Diamines Polyamines 2024

DIAMINES & POLYAMINES

Version: IB9_2

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II

Empowering Peptide Innovation With this guiding theme in mind, Iris Biotech’s mission is to support researchers by supplying • innovative technologies, • rare compounds, • as well as a broad portfolio on standard consumables, available in flexible quantities from small scale to bulk quantities. To fulfill our dedication “Empowering Peptide Innovation”, we are attending various conferences, symposia, and exhibitions each year. This allows us to remain in direct contact with scientists all over the world, both from academia and industry, to exchange knowledge, and to gather new ideas to tackle your current challenges.

Guided by our dedication to provide • competent service, • as well as novel substances and • latest technologies, Iris Biotech is your trusted partner for the world of peptides, while having strong expertise in associated disciplines. Thus, our portfolio comprises reagents and tools for the synthesis and modification of peptides, e.g. amino acids, resins and solvents but also for related technologies such as Drug Delivery, Linkerology® and Life Sciences.

Amino Acids

Building Blocks

Life Sciences

Drug Delivery

Reagents

Resins

Linkerology®

Click Chemistry

Owed to the growing demand for tailor-made compounds, our portfolio is fine-tuned by our Custom Synthesis Service at Iris Biotech Laboratories. Our skilled scientists offer profound expertise in • de novo route development, • upscaling towards larger scale production, • as well as synthesis optimization for increased efficiency.

Examples are the synthesis of rare chiral building blocks, unnatural amino acid derivatives, sophisticated orthogonal protecting groups, heterocycles, building blocks for nucleotides, PEGs and PEG-analogues as well as specific linkers for controlled drug delivery and release.

Iris Biotech GmbH • Email: info@iris-biotech.de • www.iris-biotech.de • Empowering Peptide Innovation

III

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Portfolio Overview Peptide Synthesis and Modification

Linkerology® and Drug Delivery

(Protected) Amino Acids

Linkers for Solid Phase Peptide Synthesis

Standards such as Fmoc-D/L-AAA and Boc-D/L-AAA, Smoc amino acids for peptide synthesis in water, variety of protecting groups (e.g. Pbf, Trt, tBu, Bzl, Acm,

Cleavable Linkers Val-Ala based, Val-Cit based, disulfide-based, Dde-helping

Life Sciences

Biotinylation Reagents Carbohydrates Galactose, Glucose, Maltose, Mannose, Xylose and others

hands

Drug Metabolites

Photo-Activatable Linkers

Peptides

Functionalized Linkers

Substrates & Inhibitors

Building Blocks

Clickable linkers, trifunctional

E.g. protein kinase inhibitors,

Amino alcohols, amino aldehy-

linkers, linkers with maleimide

Mob, SIT, Phacm, Allocam, Mmt), unusual amino acids, fluorinated derivatives, substituted prolines, arginine analogues

des, diamines and hydrazines, (pseudoproline) dipeptides, polyamines and spermines, fatty acid derivatives Reagents Coupling reagents, solvents and scavengers, protecting groups Resins Preloaded resins (e.g. based on Trityl, TCP, TentaGel, Methoxybenzhydryl, Merrifield, PAM, Rink, Wang), scavenger resins, hydrazone resins

function, cross-linkers, selective N-term acylation and biotiny-

substrates for fusion (Halo/ Snap/Clip)-tagged proteins

lation

Natural Products

PROTACs

Dyes and Fluorescent Labels

Ligands, linkers & modules

E.g. ICG, AMC, DAPI

Fullerenes, Poly(2-oxazolines) & Dextrans

Maillard & Amadori Reaction Products

Poly-Amino Acids Poly-Arg, Poly-Glu, Poly-Lys, Poly-Orn, Poly-Sar PEGylation Branched PEGylating reagents, (amino-)PEG-acids, PEG-amines & hydrazides & guanidines, reagents for Click-conjugation, Biotin-PEG-reagents, PEG-thiols, PEG-maleimides, other PEGylating reagents

Large portfolio of derivatives useful as standards for food, pharma and cosmetics industry Vitamins

Custom Synthesis Your project requires a compound not listed in our portfolio?

Get in contact and inquire about our custom synthesis capabilities.

Our experienced scientists are excited to accept your synthetic challenge!

In such cases, your request undergoes the following stages:

search Step-by-Step Analysis

Process Evaluation

Strategy Development

Quality Consistency

• Customer’s demands

• Detailed literature review • Synthetic possibilities

• Protocol development • Method development and validation • Customized synthesis

• Identity confirmation • Purity verification

Our Service Promise All our services are based on high standards, transparency & documentation, trust, honesty & confidentiality, as well as the required know-how.

High Standards

Transparency & Documentation

• Values: sustainability & responsibility

• Talk to our specialists – customer care

• State-of-the-art equipment & latest

• Certificates of analysis & impurity profiling

technologies

• Analytical and process reports

• High quality standards • Qualified suppliers & regular audits

Trust, Honesty & Confidentiality

Our Know-How

• Intergenerational business valuing

• One-step reactions & complex

partnerships

multi-step synthesis

• Meeting the customer‘s expectations

• Scalability from mg to kg quantities

• Integrity towards our customers

• Route scouting

Iris Biotech GmbH • Email: info@iris-biotech.de • www.iris-biotech.de • Empowering Peptide Innovation

V

Table of contents

Diamines & Polyamines 1.

Background

1

2. Spermines and other Biogenic Polyamines

3

3. Linear Diaminoalkanes

9

4. PEG-based linear Diamines

20

5. Cyclic Amines

22

Code of Conduct

27

Terms and Conditions of Sales

29

Index

33

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VII

Diamines & Polyamines

1. Background .

Polyamines are aliphatic cations with multiple functions in cell proliferation and differentiation and are essential for normal cell growth and development in eukaryotes. These molecules carry positive charges at their primary and secondary amino groups at physiological pH. Consequently, polyamines bind to various anionic macromolecules including DNA, RNA, acidic phospholipids, and certain proteins. These polycationic alkylamines are involved in various critical cellular functions, such as maintaining chromatin structure, regulating ion-channels, maintaining membrane stability, modulating protein synthesis, and scavenging free radicals. Polyamines also serve as substrates for transglutaminase reactions and for the synthesis of the translational regulator hypusine.

Crucial parts of the biological function of polyamines are the regulation of gene expression by altering DNA structure, the modulation of protein synthesis by binding to RNA, and the modulation of signal transduction pathways. The binding of polyamines to both RNA and DNA leads to conformational changes of those nucleic acids. Polyamines cause the conformational transition of DNA from the B form to the Z form and also cause bending of DNA. Both structural alterations are known to influence transcription. Close to 80% of all polyamines in the cell are associated with RNA, while spermine in particular has been shown to stabilize tRNA structures. Binding of polyamines to RNA causes structural changes that increase the efficiency of protein synthesis.

Polyamines are also known to modulate DNA-protein interactions, e.g. by enhancing the binding of specific gene-regulatory proteins to certain regulatory sequences termed response elements. The polyamine spermine has been reported to facilitate the binding of estrogen receptor and nuclear factor κB (NF-κB) to their respective response elements at 100 to 500 μM concentrations. Polyamines are also involved in modulating ligand-receptor interactions, for example N-methyl-D-aspartate (NMDA) receptors, which are important for the excitatory synaptic transmission in the brain and spinal cord.

Moreover, polyamines have been implicated as important molecules in virus-host interactions since many viruses utilize and manipulate polyamines for their own replication. Those pathogens depend on the presence of polyamines for numerous aspects of their replication cycles, such as DNA and RNA polymerization, genome packaging, and viral protein translation. Certain viruses even appear to stimulate polyamine synthesis upon infection, a fact that underlines the importance of this class of molecules for the viral life cycle.

The polyamine metabolic pathway and thus polyamine levels are strictly regulated in cells. However, dysregulation of polyamine metabolism is a frequently observed event in cancer. For example, elevated levels of polyamines have been associated with breast, colon, prostate, and skin cancers. Consequently, polyamine synthesis, metabolism, uptake, and function may be promising targets for cancer therapy.

References: → Polyamine metabolism and cancer: treatments, challenges and opportunities; R. A. Casero, Jr., T. Murray Stewart, A. E. Pegg; Nat Rev Cancer 2018; 18: 681-695. https://doi.org/10.1038/s41568-018-0050-3 → Polyamines and Their Role in Virus Infection; B. C. Mounce, M. E. Olsen, M. Vignuzzi, J. H. Connor; Microbiol. Mol. Biol. Rev. 2017; 81: e00029-17. https://doi.org/10.1128/MMBR.00029-17 → Targeting polyamine metabolism for cancer therapy and prevention; T. R. Murray-Stewart, P. M. Woster, R. A. Casero, Jr.; Biochem J 2016; 473: 2937-53. https://doi.org/10.1042/BCJ20160383 → Polyamine catabolism in carcinogenesis: potential targets for chemotherapy and chemoprevention; V. Battaglia, C. DeStefano Shields, T. Murray-Stewart, R. A. Casero, Jr.; Amino Acids 2014; 46: 511-9. https://doi.org/10.1007/s00726-013-1529-6 → Translational recoding as a feedback controller: systems approaches reveal polyamine-specific effects on the antizyme ribosomal frameshift; C. Rato, S. R. Amirova, D. G. Bates, I. Stansfield, H. M. Wallace; Nucleic Acids Res 2011; 39: 4587-97. https://doi.org/10.1093/nar/gkq1349

1

Iris Biotech GmbH • Email: info@iris-biotech.de • www.iris-biotech.de • Empowering Peptide Innovation

→ Synthesis and applications of polyamine amino acid residues: improving the bioactivity of an analgesic neuropeptide, neurotensin; L. Zhang, H. K. Lee, T. H. Pruess, H. S. White, G. Bulaj; J Med Chem 2009; 52: 1514-7. https://doi.org/10.1021/jm801481y → Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases; R. A. Casero, Jr., L. J. Marton; Nat Rev Drug Discov 2007; 6: 373-90. https://doi.org/10.1038/nrd2243 → The critical roles of polyamines in regulating ColE7 production and restricting ColE7 uptake of the colicin-producing Escherichia coli; Y. H. Pan, C. C. Liao, C. C. Kuo, K. J. Duan, P. H. Liang, H. S. Yuan, S. T. Hu, K. F. Chak; J Biol Chem 2006; 281: 13083-13091. https://doi.org/10.1074/jbc.M511365200 → Structural analysis of DNA interactions with biogenic polyamines and cobalt(III)hexamine studied by Fourier transform infrared and capillary electrophoresis; A. A. Ouameur, H. A. Tajmir-Riahi; J Biol Chem 2004; 279: 42041-54. https://doi.org/10.1074/jbc.M406053200 → Defining the molecular requirements for the selective delivery of polyamine conjugates into cells containing active polyamine transporters; C. Wang, J. G. Delcros, L. Cannon, F. Konate, H. Carias, J. Biggerstaff, R. A. Gardner, I. V. O. t. Phanstiel; J Med Chem 2003; 46: 5129-38. https://doi.org/10.1021/jm030223a → Role of polyamines and ethylene as modulators of plant senescence; S. Pandey, S. A. Ranade, P. K. Nagar, N. Kumar; J Biosci 2000; 25: 291-9. https://doi.org/10.1007/BF02703938

O NH2+

-O

P

O

O O

NH2+

H

P

N

N

H

N HN

O

O

N O

O

H H

O

O

N

H

N N

HN

H

O

H2N

+

O-

P

N

+

O

NH

N O

O-

P

N

O

O

NH

N

O -O

O

N

H2N

O O O

Fig. 1: Electrostatic interaction between polyamines and oligonucleotides.

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2

Diamines & Polyamines

2.

Spermines . and other Biogenic Polyamines Polyamines stabilize nucleic acids against chemical and enzymatic degradation, facilitate the formation of secondary and tertiary structures and enhance cellular uptake. Biogenic polyamines, such as putrescine and spermidine are involved in numerous diverse biological processes. Due to their binding to DNA and RNA they play an important role in nucleic acid function and cause DNA condensation and aggregation inducing DNA conformational changes.

References: → Structural analysis of DNA interactions with biogenic polyamines and cobalt(III)hexamine studied by Fourier transform infrared and capillary electrophoresis; A. A. Ouameur, H. A. Tajmir-Riahi; J Biol Chem 2004; 279: 42041-54. https://doi.org/10.1074/jbc.M406053200 → The synthesis and properties of oligoribonucleotide-spermine conjugates; A. J. Marsh, D. M. Williams, J. A. Grasby; Org Biomol Chem 2004; 2: 2103-12. https://doi.org/10.1039/b404150j → Spermine participates in oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation; M. E. Hosford, J. G. Muller, C. J. Burrows; J Am Chem Soc 2004; 126: 9540-1. https://doi.org/10.1021/ja047981q → Quadruplex structures in nucleic acids; M. A. Keniry; Biopolymers 2000; 56: 123-46. https://doi.org/10.1002/1097-0282(2000/2001)56:3<123::AID-BIP10010>3.0.CO;2-3

Alkyl-Oligoamines Product details

BNN1350

DETA(BHH*2HCl)

tert-butyl (2-((2-aminoethyl)amino)ethyl)carbamate dihydrochloride CAS-No. Formula Mol. weight

162279-67-6 C9H21N3 O 2*2HCl 203,29*72,92 g/mol

BNN1330

DETA(HBH)*2HCl

O O

H N

N H

NH2

tert-butyl bis(2-aminoethyl)carbamate CAS-No. Formula Mol. weight

1914917-65-9 C9H21N3 O 2*2HCl 203,29*72,92 g/mol

O N

H2N

BNN1340

3

NH2

DPTA(BHB)*HCl

di-tert-butyl (azanediylbis(propane-3,1-diyl))dicarbamate CAS-No. Formula Mol. weight

O

H N

O O

H N

H N

O O

82409-03-8 C16H33N3 O4*HCl 331,46*36,46 g/mol

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Product details

BNN1080

1,4-Bis-Boc-1,4,7-triazaheptane

1,4-Bis-t-butyloxycarbonyl-1,4,7-triazaheptane CAS-No. Formula Mol. weight

120131-72-8 C14H29N3 O4 303,4 g/mol

BNN1090

1,7-Bis-Boc-1,4,7-triazaheptane

1,7-Bis-t-butyloxycarbonyl-1,4,7-triazaheptane CAS-No. Formula Mol. weight

117499-16-8 C14H29N3 O4 303,4 g/mol

BNN1100

1,5-Bis-Boc-1,5,9-triazanonane

O

122248-82-2 C16H33N3 O4 331,45 g/mol

BNN1110

1,9-Bis-Boc-1,5,9-triazanonane

1,9-Bis-t-butyloxycarbonyl-1,5,9-triazanonane CAS-No. Formula Mol. weight

82409-02-7 C16H33N3 O4 331,45 g/mol

BNN1120

1,5-Bis-Boc-1,5,10-triazadecane 85503-20-4 C17H35N3 O4 345,48 g/mol

BNN1130

1,6-Bis-Boc-1,6,10-triazadecane

O

O

O HN

O

O NH

N H

O O

N H

N O

O

NH2 O

O

O H N

HN

1,5-Bis-t-butyloxycarbonyl-1,5,10-triazadecane CAS-No. Formula Mol. weight

NH2

N

O

1,5-Bis-t-butyloxycarbonyl-1,5,9-triazanonane CAS-No. Formula Mol. weight

H N

O

O NH

O O

N H

NH2

N O

O

1,6-Bis-t-butyloxycarbonyl-1,6,10-triazadecane CAS-No. Formula Mol. weight

68076-39-1 C17H35N3 O4 345,48 g/mol

O

O O

N H

O N

NH2

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4

Diamines & Polyamines Product details

FNN1040

Fmoc-DETA(Boc)-Suc-OH

N1-(9-Fluorenylmethyloxycarbonyl)-N2-(t-butyloxycarbonyl)-N3 -diethylene-triamine-succinamic acid CAS-No. Formula Mol. weight

1373763-34-8 C 28H35N3 O 7 525,59 g/mol

SNN1040

Spermine(HBBB)

O

O

O N H

O

N2,N3 ,N4-Tris-(t-butyloxycarbonyl)-1,5,10,14-tetra-aza-quatrodecan CAS-No. Formula Mol. weight

114459-62-0 C 25H 50 N4O 6 502,7 g/mol

SNN1080

Spermine(HBBH)

O

H2N

177213-61-5 C 20 H42N4O4 402,58 g/mol

SNN1200

Spermine(BHHB)

CAS-No. Formula Mol. weight

140652-55-7 C 20 H42N4O4 402,57 g/mol

SNN1140

Spermine(FBBSuc-OH)

1263046-90-7 C 39H 56N4O 9 724,9 g/mol

SNN1220

Spermine(BBBSuc)

H N

N O

N H

N H

O

N H

NH2

H N

H N

O

O

H N

N

N O

O O

O O

O N

O

O O

O O

O

H2N

N2,N3 -Bis-(t-butyloxycarbonyl)-N1-(9-fluorenylmethyloxycarbonyl)-1,5,10,14-tetra-aza-quatrodecan-N4-succinamic acid CAS-No. Formula Mol. weight

O

O

N1,N4-Bis-(t-butyloxycarbonyl)-1,5,10,14-tetra-aza-tetradecan

O

N

N O

OH

N H

N2,N3 -Bis-(t-butyloxycarbonyl)-1,5,10,14-tetra-aza-quatrodecan CAS-No. Formula Mol. weight

O

N

OH O

O

N1,N5,N10-triBoc-N14-succinoyl Spermine CAS-No. Formula Mol. weight

5

1247874-32-3 C 29H 54N4O 9 602,77 g/mol

O

O O

N H O

O N

N O

O

H N

OH O

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Product details

SNN1240

Spermine(SucBBSuc)

N5,N10-bisBoc-N1,N14-bisSuccinoyl Spermine Formula Mol. weight

C 28H 50 N4O 10 602,73 g/mol

SNN1190

Spermine(BBBB-CO2H) (S)

N H

O

119798-08-2 C 31H 58N4O 10 646,81 g/mol

SNN1130

Spermine(HHHStea)*3HCl

O

CAS-No. Formula Mol. weight

273935-54-9net C 28H 60 N4O*3HCl 468,82*109,35 g/mol

SNN1170

Spermine(HHHN3)*3HCl

N1-(3-Aminopropyl)-N4-(3-azidopropyl)butane-1,4-diamine trihydrochloride CAS-No. Formula Mol. weight

1823475-98-4 C10 H24N 6*3HCl 228,34*109,38 g/mol

SNN1210

Spermine(N3HHN3)*2TsOH

N1-(3-Aminopropyl)-N4-(3-azidopropyl)butane-1,4-diamine bistosylate

O

N

OH (S)

N H

N3

N H

CAS-No. Formula Mol. weight

2250433-79-3 net C10 H22N 8*C14H16O 6 S 2 254,34*344,40 g/mol

BNN1160

8,11-bis(Boc)-1,8,11,18-tetraazaoktadecane

N H

O

H N

O

O

H N

N H

H2N

O

N

O

H2N

OH O

O

N1-Stearoyl-1,5,10,14-tetra-aza-quatrodecan trihydrochloride

O

H N

O

O

H N

O

O N

N O

(S)-N1,N5,N10,N14-Tetrakis-(t-butyloxycarbonyl)-1,5,10,14-tetraazatetradecan-9-carboxylic acid CAS-No. Formula Mol. weight

O

O HO

H N

N3

H N

N3

tert-butyl ethane-1,2-diylbis(6-aminohexylcarbamate) CAS-No. Formula Mol. weight

216504-14-2 C 24H 50 N4O4 458,68 g/mol

O

H2N

O N

NH2

N O

O

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Diamines & Polyamines Product details

HNN1100

H-TETA(Boc2)-H

N2,N3 -bis-Boc-triethylene tetramine CAS-No. Formula Mol. weight

206531-21-7 C16H34N4O4 346,47 g/mol

FNN1045

Fmoc-TETA(Boc2)-Suc-OH

O

H2N

2389064-35-9 C 35H48N4O 9 668,78 g/mol

BNN1310

Fmoc-TEPA(Boc3)-Suc

2304536-78-3 C 42H 61N 5O 11 811,96 g/mol

FNN1130

Fmoc-TEPA(Boc3)-DIG

C 42H 61N 5O 12 827,97 g/mol

BNN1300

TEPA(HBBBH)

7

556082-09-8 C 23H47N 5O 6 489,65 g/mol

O N

N H

O

O O

O

O

O O

O

H2N

O N

N O

O

O N H

O

O O

O N

N O

OH O

O

O N

O N H

O

O N

N H

O N

N

OH O

O

O N

N H

O

H N

N

O

t-butyl N,N-bis({2-[(2-aminoethyl)[(t-butoxy)carbonyl] amino]ethyl})carbamate CAS-No. Formula Mol. weight

O

O

7,10,13-tris(tert-butoxycarbonyl)-1-(9H-fluoren-9-yl)-3,17-dioxo-2,19-dioxa-4,7,10,13,16-pentaazahenicosan-21-oic acid Formula Mol. weight

O

O O

3-[(2-{[(t-butoxy)carbonyl](2-{[(t-butoxy)carbonyl] (2-{[(t-butoxy)carbonyl][2-({[(9H-fluoren-9-yl)methoxy] carbonyl}amino)ethyl]amino}ethyl)amino}ethyl)amino} ethyl)carbamoyl]propanoic acid CAS-No. Formula Mol. weight

NH2

N O

N1-Fmoc-N2,N3 -bis-Boc-triethylene-tetramine-N4-succinamic acid CAS-No. Formula Mol. weight

O N

NH2

O

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OH

Procedure for the removal of Boc: • Dissolve 3 mmol Boc protected spermine in 80 ml 1M HCl in MeOH. • Stir the mixture at 25 °C for 6 h.

• The progress of the deprotection can be monitored by TLC (Toluene:EtOH:AcOH 40:10:1).

After completion evaporate the solution under vacuum by rotavapor to dryness.

• Redissolve with ca. 50 ml methylene chloride and evaporate again to dryness.

• The remaining sticky, glassy oil should be immediately dissolved in the solvent for the next chemical transformation and used without keeping to next day.

• In case this is not possible, the product can be stored under inert, dry atmosphere for some days at +4 °C in toluene, which is adjusted to pH 4 with a few drops of AcOH.

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8

Diamines & Polyamines

3. Linear .

Diaminoalkanes Hydrazines Product details

BNN1009

Boc3 -Hydrazine O

Tris-(t-Butyloxycarbonyl)-hydrazine CAS-No. Formula Mol. weight

185456-26-2 C15H28N2O 6 332,4 g/mol

BNN1039

Boc-HNNH-Z 57699-88-4 C13H18N2O4 266,3 g/mol

BNN1006

Boc,Z-NNH-Boc

O N H

O

CAS-No. Formula Mol. weight

202980-91-4 C18H26N2O 6 366,42 g/mol

BNN1021

Boc-HNNH-PPh3 Br

9

356534-53-7 C 23H26BrN2O 2P 473,35 g/mol

O

O

H N

O

O

O O

O

O

N

O

1-(t-Butyloxycarbonyl)-2-triphenylphosphonium-hydrazine Bromide CAS-No. Formula Mol. weight

H N

O

N,N‘-di-(t-Butyloxycarbonyl)-N-benzyloxycarbonyl-hydrazine

H N

O

O

1-(t-Butyloxycarbonyl)-2-benzyloxycarbonyl-hydrazine CAS-No. Formula Mol. weight

N

O

N H

H N

O O

P+

Br-

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Ethylenediamines Product details

BNN1018

Boc-EDA, liq.

O

N-t-Butyloxycarbonyl-ethylenediamine CAS-No. Formula Mol. weight

57260-73-8 C 7H16N2O 2 160,2 g/mol

BNN1017

Boc-EDA*HCl O

N-t-Butyloxycarbonyl-ethylenediamine hydrochloride CAS-No. Formula Mol. weight

79513-35-2 C 7H16N2O 2*HCl 160,2*36,45 g/mol

BNN1005

Boc,Me-EDA 121492-06-6 C 8H18N2O 2 174,2 g/mol

BNN1034

Boc,Me-EDA*HCl

O

202207-78-1 C 8H18N2O 2*HCl 174,2*36,45 g/mol

BNN1057

Boc,Me-EDA-Me*HCl

Me

O

202207-84-9 C9H20 N2O 2*HCl 188,2*36,45 g/mol

NH2

N

O

Me

O

N-t-Butyloxycarbonyl-N,N‘-dimethyl-1,2-ethylenediamine hydrochloride CAS-No. Formula Mol. weight

NH2

N

O

N-t-Butyloxycarbonyl-N-methyl-1,2-ethylenediamine hydrochloride CAS-No. Formula Mol. weight

NH2

N H

O

N-t-Butyloxycarbonyl-N-methyl-ethylenediamine CAS-No. Formula Mol. weight

NH2

N H

O

O

N

H N

Me

Me

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10

Diamines & Polyamines Product details

BNN1036

Boc-EDA-Et*HCl O

N-t-Butyloxycarbonyl-N‘-ethyl-1,2-ethylenediamine hydrochloride Formula Mol. weight

C9H20 N2O 2*HCl 188,25*36,45 g/mol

BNN1003

Boc,Et-EDA*HCl

N H

O

C9H20 N2O 2*HCl 188,25*36,45 g/mol

BNN1038

Boc,Pr-EDA 105628-64-6 C10 H22N2O 2 202,1 g/mol

BNN1019

Boc-EDA-Bzl*HCl

Et

O

126402-64-0 C14H22N2O 2*HCl 250,3*36,45 g/mol

BNN1037

Boc,Bzl-EDA*HCl

O

152193-00-5 C14H22N2O 2*HCl 250,3*36,5 g/mol

BNN1380

Boc-EDA-Suc-OH

O O

Boc,Succinoyl-ethylenediamine CAS-No. Formula Mol. weight

11

891781-87-6 C11H20 N2O 5 260,29 g/mol

H N

N H

O

N-t-Butyloxycarbonyl-N-benzyl-ethylenediamine hydrochloride CAS-No. Formula Mol. weight

NH2

N

O

N-t-Butyloxycarbonyl-N‘-benzyl-ethylenediamine hydrochloride CAS-No. Formula Mol. weight

NH2

N

O

N-t-Butyloxycarbonyl-N-propyl-ethylenediamine CAS-No. Formula Mol. weight

Et

O

N-t-Butyloxycarbonyl-N-ethyl-ethylenediamine hydrochloride Formula Mol. weight

H N

O O

N H

NH2

N

O

H N

OH O

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Product details

FNN1008

Fmoc-EDA*HCl

N1-(9-Fluorenylmethyloxycarbonyl)-ethylenediamine hydrochloride CAS-No. Formula Mol. weight

391624-46-7 C17H18N2O 2*HCl 318,8 g/mol

FNN1020

Fmoc-EDA-N3

O

1-[(9-Fluorenylmethyloxycarbonyl)amino]-2-azidoethane CAS-No. Formula Mol. weight

432507-62-5 C17H16N4O 2 308,33 g/mol

NNN1003

Ns-EDA-Boc

N-(2-Nitrobenzenesulfonyl)-N‘-(t-Butyloxycarbonyl)-1,2-diaminoethane Formula Mol. weight

C13H19N3 O 6 S 345,38 g/mol

ZNN1002

Z-EDA*HCl

O

O

O S

18807-71-1 C10 H14N2O 2*HCl 230,69 g/mol

ZNN1048

Z-EDA-EDA-Z

H N

N H

C 20 H25N3 O4 371,4 g/mol

O O

NO2

O

O O

N H

NH2

N H

O

N,N“-Di-benzyloxycarbonyl-diethylenetriamine Formula Mol. weight

N3

N H

O

N1-Benzyloxycarbonyl-ethylenediamine hydrochloride CAS-No. Formula Mol. weight

NH2

N H

O

H N

O N H

O

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12

Diamines & Polyamines Diaminopropanes Product details

BNN1052

Boc-DAP O

N-t-Butyloxycarbonyl-1,3-diaminopropane CAS-No. Formula Mol. weight

75178-96-0 C 8H18N2O 2 174,24 g/mol

BNN1013

Boc-DAP*HCl

O

127346-48-9 C 8H18N2O 2*HCl 174,24*36,45 g/mol

BNN1004

Boc,Me-DAP*HCl

O

1188263-67-3 C9H20 N2O 2*HCl 188,25*36,45

FNN1004

Fmoc-DAP*HCl

N H

NH2

N

NH2

O

N-t-Butyloxycarbonyl-N-methyl-1,3-diaminopropane hydrochloride CAS-No. Formula Mol. weight

NH2

O

N-t-Butyloxycarbonyl-1,3-diaminopropane hydrochloride CAS-No. Formula Mol. weight

N H

O

Me

N1-(9-Fluorenylmethyloxycarbonyl)-1,3-diaminopropane hydrochloride CAS-No. Formula Mol. weight

210767-37-6 C18H20 N2O 2*HCl 296,36*36,45 g/mol

FNN1030

Fmoc-DAP-N3

O

1-[(9-Fluorenylmethyloxycarbonyl)amino]-3-azidopropane CAS-No. Formula Mol. weight

13

1021422-85-4 C18H18N4O 2 322,36 g/mol

NH2

N H

O

O O

N H

N

N+

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N-

Product details

NNN1001

Ns-DAP*HCl O

N-Nosyl-1,3-diaminopropane hydrochloride CAS-No. Formula Mol. weight

863983-46-4 C9H13N3 O4 S*HCl 259,29*36,45 g/mol

NNN1004

Ns-DAP-Boc

C14H21N3 O 6 S 359,4 g/mol

ZNN1000

Z-DAP*HCl

O

O

O S

N H

N H

O

NO2

O

N1-Benzyloxycarbonyl-1,3-diaminopropane hydrochloride CAS-No. Formula Mol. weight

NH2

N H

NO2

N-(2-Nitrobenzenesulfonyl)-N‘-(t-Butyloxycarbonyl)-1,3-diaminopropane Formula Mol. weight

O S

NH2

N H

O

17400-34-9 C11H16N2O 2*HCl 208,26*36,45 g/mol

Diaminobutanes Product details

BNN1012

Boc-DAB*HCl O

N-t-Butyloxycarbonyl-1,4-diaminobutane hydrochloride CAS-No. Formula Mol. weight

33545-98-1 C9H20 N2O 2*HCl 224,8 g/mol

BNN1070

Boc-DAB-Bzl*HCl

N1-t-Butyloxycarbonyl-N4-benzyl-1,4-diaminobutane hydrochloride CAS-No. Formula Mol. weight

90914-09-3 net C16H26N2O 2*HCl 278,39*36,45 g/mol

O O

NH2

N H

O

N H

H N

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Diamines & Polyamines Product details

FNN1003

Fmoc-DAB*HCl

N1-(9-Fluorenylmethyloxycarbonyl)-1,4-diaminobutane hydrochloride CAS-No. Formula Mol. weight

321660-77-9 C19H22N2O 2*HCl 346,9 g/mol

TNN1000

Trt-DAB*AcOH

O NH2

N H

O

1-(Tritylamino)-butyl-4-ammonium acetate CAS-No. Formula Mol. weight

1173021-69-6 C 23H26N2*C 2H4O 2 330,48*60,05 g/mol

ZNN1047

Z-DAB*HCl O

N1-Benzyloxycarbonyl-1,4-diaminobutane hydrochloride CAS-No. Formula Mol. weight

NH2

N H

N H

O

18807-73-3 C12H18N2O 2*HCl 258,74 g/mol

NH2

Diaminopentanes Product details

ANN1010

Aloc-DAPe*HCl

N1-Allyloxycarbonyl-1,5-diaminopentane hydrochloride CAS-No. Formula Mol. weight

1049722-41-9 C9H18N2O 2*HCl 186,25*36,45 g/mol

BNN1014

Boc-DAPe*HCl

N-t-Butyloxycarbonyl-1,5-diaminopentane hydrochloride CAS-No. Formula Mol. weight

15

77835-31-5 C10 H22N2O 2*HCl 202,29*36,45 g/mol

O N H

O

NH2

O O

N H

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NH2

Product details

FNN1005

Fmoc-DAPe*HCl

N1-(9-Fluorenylmethyloxycarbonyl)-1,5-diaminopentane hydrochloride CAS-No. Formula Mol. weight

177333-17-4 C 20 H24N2O 2*HCl 360,9 g/mol

ZNN1001

Z-DAPe*HCl

O

O

N1-Benzyloxycarbonyl-1,5-diaminopentane hydrochloride CAS-No. Formula Mol. weight

NH2

N H

O

NH2

N H

O

18807-74-4 C13H20 N2O 2*HCl 272,77 g/mol

Diaminohexanes Product details

BNN1170

Boc-Cystamine

2-(t-Butyloxycarbonylamino)ethyldithio-2‘-ethylamine CAS-No. Formula Mol. weight

485800-26-8 C9H20 N2O 2 S 2 252,40 g/mol

BNN1063

Boc-Cystamine*HCl

2-(t-Butyloxycarbonylamino)ethyldithio-2‘-ethylamine hydrochloride CAS-No. Formula Mol. weight

93790-49-9 C9H20 N2O 2 S 2*HCl 252,40*36,45 g/mol

FNN1009

Fmoc-HMD*HCl

H N

O

945923-91-1 C 21H26N2O 2*HCl 374,9 g/mol

S

NH2

O

H N

O

S

S

NH2

O

N1-(9-Fluorenylmethyloxycarbonyl)-1,6-hexamethylenediamine hydrochloride CAS-No. Formula Mol. weight

S

O O

N H

NH2

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Diamines & Polyamines Product details

HNN1090

N3 -Cystamine*HCl

Azido-cystamine hydrochloride CAS-No. Formula Mol. weight

1807512-40-8 net C 4H10 N4 S 2*HCl 178,28*36,45 g/mol

PAA1170

Poc-Cystamine*HCl

Prop-2-yn-1-yl (2-((2-aminoethyl)disulfaneyl)ethyl) carbamate CAS-No. Formula Mol. weight

1266354-28-2 net C 8H14N2O 2 S 2*HCl 234,33*36,45 g/mol

TNN1003

Trt-HMD*AcOH

-N

N+

N

S

S

H2N

S

S

NH2

H N

O O

1-(Tritylamino)-hexyl-6-ammonium acetate CAS-No. Formula Mol. weight

325708-26-7 C 25H30 N2*C 2H4O 2 358,53*60,05 g/mol

N H

NH2

Higher Diaminoalkyl Homologues Product details √

BNN1210

Boc-DAHep*HCl

N1-t-Butyloxycarbonyl-1,7-diaminoheptane hydrochloride CAS-No. Formula Mol. weight

62146-57-0 C12H26N2O 2*HCl 230,35*36,45 g/mol

BNN1220

Boc-DAOc*HCl

N1-t-Butyloxycarbonyl-1,8-diaminooctane hydrochloride CAS-No. Formula Mol. weight

17

82408-99-9 C13H28N2O 2*HCl 244,37*36,45 g/mol

O N H

O

NH2

O O

N H

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NH2

Product details

ZNN1070

Z-DAOc*HCl

N1-t-Benzyloxycarbonyl-1,8-diaminooctane hydrochloride CAS-No. Formula Mol. weight

143116-42-1 C16H26N2O 2*HCl 278,39*36,45 g/mol

BNN1230

Boc-DANon*HCl

N1-t-Butyloxycarbonyl-1,9-diaminononane hydrochloride CAS-No. Formula Mol. weight

105612-18-8 C14H30 N2O 2*HCl 258,40*36,45 g/mol

ZNN1080

Z-DANon*HCl

O

1822866-41-0 C17H28N2O 2*HCl 292,42*36,45 g/mol

BNN1240

Boc-DADec*HCl

N1-t-Butyloxycarbonyl-1,10-diaminodecane hydrochloride CAS-No. Formula Mol. weight

62146-58-1 C15H32N2O 2*HCl 272,43*36,45 g/mol

ZNN1090

Z-DADec*HCl

1051420-13-3 C18H30 N2O 2*HCl 306,44*36,45 g/mol

BNN1250

Boc-DAUnd*HCl

N1-t-Butyloxycarbonyl-1,11-diaminoundecane hydrochloride CAS-No. Formula Mol. weight

NH2

N H

O

O N H

O

NH2

O NH2

N H

O

N1-t-Benzyloxycarbonyl-1,10-diaminodecane hydrochloride CAS-No. Formula Mol. weight

NH2

O

N1-t-Benzyloxycarbonyl-1,9-diaminononane hydrochloride CAS-No. Formula Mol. weight

N H

O

O O

N H

NH2

O O

N H

NH2

937367-26-5 (net) C16H34N2O 2*HCl 286,45*36,45 g/mol

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18

Diamines & Polyamines Product details

BNN1260

Boc-DADod*HCl

N1-t-Butyloxycarbonyl-1,12-diaminododecane hydrochloride CAS-No. Formula Mol. weight

648441-48-9 C17H36N2O 2*HCl 300,48*36,45 g/mol

ZNN1110

Z-DADod*HCl

O

N1-t-Benzyloxycarbonyl-1,12-diaminododecane hydrochloride CAS-No. Formula Mol. weight

1051420-16-6 C 20 H34N2O 2*HCl 334,50*36,45 g/mol

BNN1058

Boc-DSOA*HCl

1-(t-Butyloxycarbonyl-amino)-3,6-dithio-8-octaneamine hydrochloride CAS-No. Formula Mol. weight

circle-arrow-right

19

1301739-93-4 C11H24N2O 2 S 2*HCl 280,45*36,45 g/mol

NH2

N H

O

O O

NH2

N H

O O

N H

S

S

.

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NH2

4.

PEG-based . linear Diamines Product details

BNN1016

Boc-DOOA O

1-(t-Butyloxycarbonyl-amino)-3,6-dioxa-8-octaneamine, liq.

CAS-No. Formula Mol. weight

153086-78-3 C11H24N2O4 248,32 g/mol

FNN1007

Fmoc-DOOA*HCl

1-(9-Fluorenylmethyloxycarbonyl-amino)-3,6-dioxa-8-octaneamine hydrochloride CAS-No. Formula Mol. weight

868599-73-9 C 21H26N2O4*HCl 370,45*36,45 g/mol

BNN1015

Boc-DODA

1-(t-Butyloxycarbonyl-amino)-4,9-dioxa-12-dodecanamine, liq.

CAS-No. Formula Mol. weight

101187-29-5 C15H32N2O4 304,43 g/mol

FNN1006

Fmoc-DODA*HCl

1274891-99-4 C 25H34N2O4*HCl 426,56*36,45 g/mol

BNN1028

Boc-TOTA

1-(t-Butyloxycarbonyl-amino)-4,7,10-trioxa-13-tridecanamine, liq.

CAS-No. Formula Mol. weight

NH2

O

O O

N H

O

O

NH2

O NH2

O

O

N H

O

1-(9-Fluorenylmethyloxycarbonyl-amino)-4,9-dioxa-12-dodecanamine hydrochloride CAS-No. Formula Mol. weight

O

N H

O

O O

O

N H

O

NH2

O

NH2

O O

N H

O

O

194920-62-2 C15H32N2O 5 320,43 g/mol

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20

Diamines & Polyamines Product details

FNN1011

Fmoc-TOTA*HCl

1-(9-Fluorenylmethyloxycarbonyl-amino)-4,7,10-trioxa-13-tridecanamine hydrochloride CAS-No. Formula Mol. weight

868599-75-1 C 25H34N2O 5*HCl 442,56*36,45 g/mol

BNN1150

N3 -TOTA

1-Azido-4,7,10-trioxa-13-tridecanamine CAS-No. Formula Mol. weight

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21

1162336-72-2 C10 H22N4O 3 246,31 g/mol

O O

-

N

N+

N

O

O

N H

O

O

O

O

.

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NH2

NH2

5. Cyclic .

Amines Product details

FNN1050

Fmoc-Ppd

(9H-fluoren-9-yl)methyl 4-oxopiperidine-1-carboxylate 1-Fmoc-4-piperidone CAS-No. Formula Mol. weight

204376-55-6 C 20 H19NO 3 321,37 g/mol

BNN1059

Boc-Pip(2-AM)*HCl

O

N O

O

(R,S)-1-t-Butyloxycarbonyl-2-(aminomethyl)piperidine hydrochloride

O

CAS-No. Formula Mol. weight

141774-61-0 C11H22N2O 2*HCl 214,31*36,45 g/mol

O

BNN1000

(R)-Boc-Pip(3-NH2)*HCl

N

NH2

O

(R)-1-t-Butyloxycarbonyl-3-aminopiperidine hydrochloride CAS-No. Formula Mol. weight

188111-79-7net C10 H20 N2O 2*HCl 200,28*36,45 g/mol

BNN1025

Boc-Pip(4-AM)*HCl

1-t-Butyloxycarbonyl-4-(aminomethyl)-piperidine hydrochloride CAS-No. Formula Mol. weight

359629-16-6 C11H22N2O 2*HCl 214,31*36,45 g/mol

BNN1032

Boc-Pip(4-NH2)*HCl

1-Butyloxycarbonyl-4-amino-piperidine hydrochloride CAS-No. Formula Mol. weight

87120-72-7 net C10 H20 N2O 2*HCl 200,28*36,45 g/mol

N (R)

O

NH2

O N O

NH2

O N

NH2

O

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Diamines & Polyamines Product details

BNN1023

Boc-Paz

N-(t-Butyloxycarbonyl)-piperazine CAS-No. Formula Mol. weight

57260-71-6 C9H18N2O 2 186,3 g/mol

BNN1024

Boc-Paz*HCl

N-(t-Butyloxycarbonyl)-piperazine hydrochloride Formula Mol. weight

C9H18N2O 2*HCl 186,3*36,45 g/mol

BNN1033

Boc-Paz-NH2

1-t-Butyloxycarbonyl-4-amino-piperazine CAS-No. Formula Mol. weight

118753-66-5 C9H19N3 O 2 201,27 g/mol

FNN1010

Fmoc-Paz*HCl

O

215190-22-0 C19H20 N2O 2*HCl 344,8 g/mol

BNN1022

Boc-HoPaz*HCl

N-(t-Butyloxycarbonyl)-homopiperazine hydrochloride CAS-No. Formula Mol. weight

112275-50-0 C10 H20 N2O 2*HCl 200,28*36,45 g/mol

FNN1120

Fmoc-homoPiz*HCl

N1-(9-Fluorenylmethyloxycarbonyl)-homopiperazine hydrochloride CAS-No. Formula Mol. weight

23

1823285-30-8 C 20 H22N2O 2*HCl 322,40*36,45 g/mol

NH

N

NH

O

O O

O N

N

NH2

O

N1-(9-Fluorenylmethyloxycarbonyl)-piperazine hydrochloride CAS-No. Formula Mol. weight

N

O N

NH

O

O

NH

N O

O O

N

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NH

Product details

BNN1290

Boc(2)-Oxadiazepane*HCl

2-t-Butyloxycarbonyl-1,2,5-oxadiazepane hydrochloride CAS-No. Formula Mol. weight

1350362-73-0 C9H18N2O 3*HCl 202,25*36,45 g/mol

BNN1280

Boc(1)-Triazepane

O O

N

1-t-Butyloxycarbonyl-1,2,5-triazepane CAS-No. Formula Mol. weight

1138150-46-5 C9H19N3 O 2 201,27 g/mol

BNN1270

Di-Boc(1,2)-Triazepane*HCl

O O

C14H27N3 O4*HCl 301,38*36,45 g/mol

BNN1008

Boc-1,4-trans-DACH*HCl

N-t-Butyloxycarbonyl-1,4-trans-diaminocyclohexane hydrochloride CAS-No. Formula Mol. weight

946002-43-3 C11H22N2O 2*HCl 214,31*36,45 g/mol

FNN1002

Fmoc-1,4-trans-DACH*HCl

672310-17-7 C 21H24N2O 2*HCl 372,89 g/mol

BNN1007

Boc-1,3-cis-DAMCH*HCl

N-t-Butyloxycarbonyl-1,3-cis-diaminomethyl-cyclohexane hydrochloride Formula Mol. weight

C13H26N2O 2*HCl 242,36*36,45 g/mol

NH

O O

N

O

NH

N O

O O HN

N1-(9-Fluorenylmethyloxycarbonyl)-1,4-trans-diaminocyclohexane hydrochloride CAS-No. Formula Mol. weight

N HN

1,2-Di-t-butyloxycarbonyl-1,2,5-triazepane hydrochloride Formula Mol. weight

NH

O

NH2

O O HN

NH2

HN O O

(R)

NH2 (S)

HN O O

(S)

NH2 (R)

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24

Diamines & Polyamines Product details

FNN1001

Fmoc-1,3-cis-DAMCH*HCl

N1-(9-Fluorenylmethyloxycarbonyl)-1,3-cis-diaminomethyl-cyclohexane hydrochloride Formula Mol. weight

HN O

(R)

O

C 23H28N2O 2*HCl 364,49*36,45 g/mol

HN O

(S)

O

BNN1043

O

CAS-No. Formula Mol. weight

203306-83-6 net C13H26N2O 2*HCl 242,36*36,45 g/mol

O

BNN1075

Boc-1,4-trans-DAMCH

N-t-Butyloxycarbonyl-1,4-trans-diaminomethyl-cyclohexane (oil) CAS-No. Formula Mol. weight

166168-16-7 C13H26N2O 2 242,36 g/mol

BNN1035

Boc-1,4-trans-DAMCH*HCl O

CAS-No. Formula Mol. weight

256649-59-9 C13H26N2O 2*HCl 242,36*36,45 g/mol

O

BNN1180

Boc3 -Cyclen 175854-39-4 C 23H44N4O 6 472,62 g/mol

BNN1190

Boc3 -Cyclen-COOH

NH

NH2

NH

NH2

O

O N

O

NH

N O

N O

2-(4,7,10-tris(t-butoxycarbonyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid 247193-74-4 C 25H46N4O 8 530,65 g/mol

NH2

O

N-t-Butyloxycarbonyl-1,4-trans-diaminomethyl-cyclohexane hydrochloride

CAS-No. Formula Mol. weight

NH

O

1,4,7-tri-(t-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane

25

NH2 (R)

Boc-1,4-cis-DAMCH*HCl

N-t-Butyloxycarbonyl-1,4-cis-diaminomethyl-cyclohexane hydrochloride

CAS-No. Formula Mol. weight

NH2 (S)

O

O

HO

O N

O N

O N O

N O

O

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Notes

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26

Diamines & Polyamines

Code of Conduct As business activity of Iris Biotech GmbH impacts people’s lives and health, it must be operated in ethical and correct manner and act with integrity and responsibility. To ensure high ethical standards and fair business practices, Iris Biotech GmbH applies an integrated policy known as its Code of Conduct.

In 2001 Iris Biotech GmbH was founded just at the beginning of the Biotech movement and the first remarkable breakthrough of biotech pharma products. Although the biotech field is rather young compared to other industries we believe on long-term business, a good partnership between our business partners and Iris Biotech GmbH and a good reputation. It is our duty as well as our responsibility to maintain and to extend this over the next generations – based on the principles of an honourable and prudent tradesman which based upon the concept of honourable entrepreneurship.

This Code of Conduct has been developed following the “Voluntary Guidelines for Manufacturers of Fine Chemical Intermediates and Active Ingredients” issued by AIME (Agrochemical & Intermediates Manufacturers in Europe) and the requirements of some of our business associates.

Iris Biotech GmbH commits to hold this Code of Conduct and to include and apply its principles in the management system and the company policies.

Ethics Iris Biotech GmbH undertakes business in an ethical manner and acts with integrity. All corruption, extortion and embezzlement are prohibited. We do not pay or accept bribes or participate in other illegal inducements in business or government relationships. We conduct our business in compliance with all applicable anti-trust laws. Employees are encouraged to report concerns or illegal activities in the workplace, without threat of reprisal, intimidation or harassment.

Labour Iris Biotech GmbH is committed to uphold the human rights of workers and to treat them with dignity and respect. Child labour, workplace harassment, discrimination, and harsh and inhumane treatment are prohibited. Iris Biotech GmbH respects the rights of the employees to associate freely, join or not join labour unions, seek representation and join workers’ councils. Employees are paid and their working timetable is established according to applicable wage and labour laws. Employees are able to communicate openly with management regarding working conditions without threat of reprisal, intimidation or harassment.

General Policies Contracts and Secrecy Agreements are binding and the confidential information received is only used for intended purposes. Clear management and organizational structures exist to provide efficient normal working and to address problems quickly. Know-how is protected and intellectual property isrespected.

27

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Health and Safety Iris Biotech GmbH provides a safe and healthy working environment to the employees and protects them from overexposure to chemical and physical hazards. Products are produced, stored and shipped under the guidelines of the relevant chemical and safety legislation. Risks and emergency scenarios are identified and evaluated, and their possible impact is minimized by implementing emergency plans and written procedures. Safety information regarding hazardous materials is available to educate, train and protect workers from hazards. Preventive equipment and facilities maintenance is performed at suitable periods to reduce potential hazards. Employees are regularly trained in health and safety matters and are informed about product properties and risk classification when it is required.

Environment Iris Biotech GmbH operates in an environmentally responsible and efficient manner, minimizing adverse impacts on the environment. Waste streams are managed to ensure a safe handling, movement, storage, recycling and reuse, before and after being generated. Systems to prevent and mitigate accidental spills and releases to the environment are in place. All required environmental permits and licenses are obtained and their operational and reporting requirements are complied with.

Production and Quality Management A quality management system following the Good Distribution Practices (GDP rules) of Active Pharmaceutical Ingredients is established covering all the aspects of the worldwide distribution of products.

Regular audits are performed to evaluate the efficiency and fulfilling of the quality system. Process controls to provide reproducible product quality are established. There are preventive maintenance procedures to ensure plant reliability and the lowest risk of failure. Staff is trained periodically about GMP and GDP rules. Procedures are established and installations are designed to avoid cross contamination.

Batch and analytical records are kept for inspection and audit purposes for suitable periods according guidelines.

Research and Development Research and development staff education is appropriate to their functional activity and they are trained to develop, optimize and scale-up the processes. Intellectual property is respected and knowhow protected. Development of manufacturing processes reflects the principles of the Green Chemistry according to the American Chemical Society Green Chemistry Institute. Animal testing is not used unless alternatives are not scientifically valid or accepted by regulators. If animal testing is carried out, animals are treated so that pain and stress are minimized.

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Diamines & Polyamines

Terms and Conditions of Sales All orders placed by a buyer are accepted and all contracts are made subject to the terms which shall prevail and be effective notwithstanding any variations or additions contained in any order or other document submitted by the buyer. No modification of these terms shall be binding upon Iris Biotech GmbH unless made in writing by an authorised representative of Iris Biotech GmbH.

Placing of Orders Every order made by the buyer shall be deemed an offer by the buyer to purchase products from Iris Biotech GmbH and will not be binding on Iris Biotech GmbH until a duly authorised representative of Iris Biotech GmbH has accepted the offer made by the buyer. Iris Biotech GmbH may accept orders from commercial, educational or government organisations, but not from private individuals and Iris Biotech GmbH reserves the right to insist on a written order and/or references from the buyer before proceeding.

There is no minimum order value. At the time of acceptance of an order Iris Biotech GmbH will either arrange prompt despatch from stock or the manufacture/acquisition of material to satisfy the order. In the event of the latter Iris Biotech GmbH will indicate an estimated delivery date. In addition to all its other rights Iris Biotech GmbH reserves the right to refuse the subsequent cancellation of the order if Iris Biotech GmbH expects to deliver theproduct on or prior to the estimated delivery date. Time shall not be of the essence in respect of delivery of the products. If Iris Biotech GmbH is unable to deliver any products by reason of any circumstances beyond its reasonable control („Force Majeure“) then the period for delivery shall be extended by the time lost due to such Force Majeure. Details of Force Majeure will be forwarded by Iris Biotech GmbH to the buyer as soon as reasonably practicable.

Prices, Quotations and Payments Prices are subject to change. For the avoidance of doubt, the price advised by Iris Biotech GmbH at the time of the buyer placing the order shall supersede any previous price indications. The buyer must contact the local office of Iris Biotech GmbH before ordering if further information is required. Unless otherwise agreed by the buyer and Iris Biotech GmbH, the price shall be for delivery ex-works. In the event that the buyer requires delivery of the products otherwise than ex-works the buyer should contact the local office of Iris Biotech GmbH in order to detail its requirements. Iris Biotech GmbH shall, at its discretion, arrange the buyer‘s delivery requirements including, without limitation, transit insurance, the mode of transit (Iris Biotech GmbH reserves the right to vary the mode of transit if any regulations or other relevant considerations so require) and any special packaging requirements (including cylinders).

For the avoidance of doubt all costs of delivery and packaging in accordance with the buyer‘s requests over and above that of delivery in standard packaging ex-works shall be for the buyer‘s account unless otherwise agreed by both parties. Incoterms 2020 shall apply. Any tax, duty or charge imposed by governmental authority or otherwise and any other applicable taxes, duties or charges shall be for the buyer‘s account. Iris Biotech GmbH may, on request and where possible, provide quotations for multiple packs or bulk quantities, and non-listed items. Irrespective of the type of request or means of response all quotations must be accepted by the buyer without condition and in writing before an order will be accepted by Iris Biotech GmbH. Unless agreed in writing on different terms, quotations are valid for 30 days from the date thereof. Payment terms are net 30 days from invoice date unless otherwise agreed in writing. Iris Biotech GmbH reserves the right to request advance payment at its discretion. For overseas transactions the buyer shall pay all the banking charges of Iris Biotech GmbH. The buyer shall not be entitled to withhold or set-off payment for the products for any reason whatsoever. Government/

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Iris Biotech GmbH • Email: info@iris-biotech.de • www.iris-biotech.de • Empowering Peptide Innovation

Corporate Visa and MasterCard (and other such credit cards) may be accepted on approved accounts for payment of the products. Personal credit cards are not acceptable. Failure to comply with the terms of payment of Iris Biotech GmbH shall constitute default without reminder. In these circumstances Iris Biotech GmbH may (without prejudice to any other of its rights under these terms) charge interest to accrue on a daily basis at the rate of 2% per month from the date upon which payment falls due to the actual date of payment (such interest shall be paid monthly). If the buyer shall fail to fulfil the payment terms in respect of any invoice of Iris Biotech GmbH Iris Biotech GmbH may demand payment of all outstanding balances from the buyer whether due or not and/or cancel all outstanding orders and/or decline to make further deliveries or provision of services except upon receipt of cash or satisfactory securities.

Until payment by the buyer in full of the price and any other monies due to Iris Biotech GmbH in respect of all other products or services supplied or agreed to be supplied by Iris Biotech GmbH to the buyer (including but without limitation any costs of delivery) the property in the products shall remain vested in Iris Biotech GmbH.

Shipping, Packaging and Returns The buyer shall inspect goods immediately on receipt and inform Iris Biotech GmbH of any shortage or damage within five days. Quality problems must be notified within ten days of receipt. Goods must not be returned without prior written authorisation of Iris Biotech GmbH. Iris Biotech GmbH shall at its sole discretion replace the defective products (or parts thereof) free of charge or refund the price (or proportionate price) to buyer. Opened or damaged containers cannot be returned by the buyer without the written prior agreement of Iris Biotech GmbH. In the case of agreed damaged containers which cannot be so returned, the buyer assumes responsibility for the safe disposal of such containers in accordance with all applicable laws.

Product Quality, Specifications and Technical Information Products are analysed in the Quality Control laboratories of Iris Biotech GmbH’s production partners by methods and procedures which Iris Biotech GmbH considers appropriate. In the event of any dispute concerning reported discrepancies arising from the buyer’s analytical results, determined by the buyer’s own analytical procedures, Iris Biotech GmbH reserves the right to rely on the results of own analytical methods of Iris Biotech GmbH. Certificates of Analysis or Certificates of Conformity are available at the discretion of Iris Biotech GmbH for bulk orders but not normally for prepack orders. Iris Biotech GmbH reserves the right to make a charge for such certification. Specifications may change and reasonable variation from any value listed should not form the basis of a dispute. Any supply by Iris Biotech GmbH of bespoke or custom product for a buyer shall be to a specification agreed by both parties in writing.

Technical information, provided orally, in writing, or by electronic means by or on behalf of Iris Biotech GmbH, including any descriptions, references, illustrations or diagrams in any catalogue or brochure, is provided for guidance purposes only and is subject to change.

Safety All chemicals should be handled only by competent, suitably trained persons, familiar with laboratory procedures and potential chemical hazards. The burden of safe use of the products of Iris Biotech GmbH vests in the buyer. The buyer assumes all responsibility for warning his employees, and any persons who might reasonably be expected to come into contact with the products, of all risks to person and property in any way connected with the products and for instructing them in their safe handling and use.

The buyer also assumes the responsibility for the safe disposal of all products in accordance with all applicable laws.

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Diamines & Polyamines Uses, Warranties and Liabilities All products of Iris Biotech GmbH are intended for laboratory research purposes and unless otherwise stated on product labels, in the catalogue and product information sheet of Iris Biotech GmbH or in other literature furnished to the buyer, are not to be used for any other purposes, including but not limited to use as or as components in drugs for human or animal use, medical devices, cosmetics, food additives, household chemicals, agricultural or horticultural products or pesticides. Iris Biotech GmbH offers no warranty regarding the fitness of any product for a particular purpose and shall not be responsible for any loss or damage whatsoever arising there from. No warranty or representation is given by Iris Biotech GmbH that the products do not infringe any letters patent, trademarks, registered designs or other industrial rights. The buyer further warrants to Iris Biotech GmbH that any use of the products in the United States of America shall not result in the products becoming adulterated or misbranded within the meaning of the Federal Food, Drug and Cosmetic Act (or such equivalent legislation in force in the buyer‘s jurisdiction) and shall not be materials which may not, under sections 404, 505 or 512 of the Act, be introduced into interstate commerce. The buyer acknowledges that, since the products of Iris Biotech GmbH are intended for research purposes, they may not be on the Toxic Substances Control Act 1976 („TSCA“) inventory. The buyer warrants that it shall ensure that the products are approved for use under the TSCA (or such other equivalent legislation in force in the buyer‘s jurisdiction), if applicable. The buyer shall be responsible for complying with any legislation or regulations governing the use of the products and their importation into the country of destination (for the avoidance of doubt to include, without limitation, the TSCA and all its amendments, all EINECS, ELINCS and NONS regulations). If any licence or consent of any government or other authority shall be required for the acquisition, carriage or use of the products by the buyer the buyer shall obtain the same at its own expense and if necessary produce evidence of the same to Iris Biotech GmbH on demand. Failure to do so shall not entitle the buyer to withhold or delay payment. Any additional expenses or charges incurred by Iris Biotech GmbH resulting from such failure shall be for the buyer‘s account. Save for death or personal injury caused by negligence of Iris Biotech GmbH, sole obligation of Iris Biotech GmbH and buyer‘s exclusive remedy with respect to the products proved to the satisfaction of Iris Biotech GmbH to be defective or products incorrectly supplied shall be to accept the return of said products to Iris Biotech GmbH for refund of the actual purchase price paid by the buyer (or proportionate part thereof), or replacement of the defective product (or part thereof) with alternative product. Iris Biotech GmbH shall have no liability to the buyer under or arising directly or indirectly out of or otherwise in connection with the supply of products by Iris Biotech GmbH to the buyer and/or their re-sale or use by the buyer or for any product, process or services of the buyer which in any way comprises the product in contract tort (including negligence or breach of statutory duty) or otherwise for pure economic loss, loss of profit, business, reputation, depletion of brand, contracts, revenues or anticipated savings or for any special indirect or consequential damage or loss of any nature except as may otherwise be expressly provided for in these terms. All implied warranties, terms and representations in respect of the products (whether implied by statute or otherwise) are excluded to the fullest extent permitted by law. The buyer shall indemnify Iris Biotech GmbH for and against any and all losses, damages and expenses, including legal fees and other costs of defending any action, that Iris Biotech GmbH may sustain or incur as a result of any act or omission by the buyer, its officers, agents or employees, its successors or assignees, its customers or all other third parties, whether direct or indirect, in connection with the use of any product. For the avoidance of doubt and in the event that Iris Biotech GmbH supplies bespoke or custom product to the buyer‘s design or specification, this indemnity shall extend to include any claim by a third party that the manufacture of the product for the buyer or the use of the product by the buyer infringes the intellectual property rights of any third party.

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Iris Biotech GmbH • Email: info@iris-biotech.de • www.iris-biotech.de • Empowering Peptide Innovation

General Iris Biotech GmbH shall be entitled to assign or sub-contract all or any of its rights and obligations hereunder. The buyer shall not be entitled to assign, transfer, sub-contract or otherwise delegate any of its rights or obligations hereunder. Any delay or forbearance by Iris Biotech GmbH in exercising any right or remedy under these terms shall not constitute a waiver of such right or remedy. If any provision of these terms is held by any competent authority to be invalid or unenforceable in whole or in part the validity of the other provisions of these terms and the remainder of the provision in question shall not be affected. These terms shall be governed by German Law and the German Courts shall have exclusive jurisdiction for the hearing of any dispute between the parties save in relation to enforcement where the jurisdiction of the German Courts shall be non-exclusive.

Notes

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Diamines & Polyamines

Index

33

Product code

Product name

BNN1000

(R)-Boc-Pip(3-NH2)*HCl

BNN1080

Page

Product code

Product name

Page

22

BNN1058

Boc-DSOA*HCl

19

1,4-Bis-Boc-1,4,7-triazaheptane

4

BNN1017

Boc-EDA*HCl

10

BNN1120

1,5-Bis-Boc-1,5,10-triazadecane

4

BNN1018

Boc-EDA, liq.

10

BNN1100

1,5-Bis-Boc-1,5,9-triazanonane

4

BNN1019

Boc-EDA-Bzl*HCl

11

BNN1130

1,6-Bis-Boc-1,6,10-triazadecane

4

BNN1036

Boc-EDA-Et*HCl

11

BNN1090

1,7-Bis-Boc-1,4,7-triazaheptane

4

BNN1380

Boc-EDA-Suc-OH

11

BNN1110

1,9-Bis-Boc-1,5,9-triazanonane

4

BNN1021

Boc-HNNH-PPh3 Br

9

BNN1160

8,11-bis(Boc)-1,8,11,18-tetraazaoktadecane

6

BNN1039

Boc-HNNH-Z

9

ANN1010

Aloc-DAPe*HCl

15

BNN1022

Boc-HoPaz*HCl

23

BNN1280

Boc(1)-Triazepane

24

BNN1023

Boc-Paz

23

BNN1290

Boc(2)-Oxadiazepane*HCl

24

BNN1024

Boc-Paz*HCl

23

BNN1037

Boc,Bzl-EDA*HCl

11

BNN1033

Boc-Paz-NH2

23

BNN1003

Boc,Et-EDA*HCl

11

BNN1059

Boc-Pip(2-AM)*HCl

22

BNN1004

Boc,Me-DAP*HCl

13

BNN1025

Boc-Pip(4-AM)*HCl

22

BNN1005

Boc,Me-EDA

10

BNN1032

Boc-Pip(4-NH2)*HCl

22

BNN1034

Boc,Me-EDA*HCl

10

BNN1028

Boc-TOTA

20

BNN1057

Boc,Me-EDA-Me*HCl

10

BNN1180

Boc3-Cyclen

25

BNN1038

Boc,Pr-EDA

11

BNN1190

Boc3-Cyclen-COOH

25

BNN1006

Boc,Z-NNH-Boc

9

BNN1009

Boc3-Hydrazine

9

BNN1007

Boc-1,3-cis-DAMCH*HCl

24

BNN1350

DETA(BHH*2HCl)

3

BNN1043

Boc-1,4-cis-DAMCH*HCl

25

BNN1330

DETA(HBH)*2HCl

3

BNN1008

Boc-1,4-trans-DACH*HCl

24

BNN1270

Di-Boc(1,2)-Triazepane*HCl

24

BNN1075

Boc-1,4-trans-DAMCH

25

BNN1340

DPTA(BHB)*HCl

3

BNN1035

Boc-1,4-trans-DAMCH*HCl

25

FNN1001

Fmoc-1,3-cis-DAMCH*HCl

25

BNN1170

Boc-Cystamine

16

FNN1002

Fmoc-1,4-trans-DACH*HCl

24

BNN1063

Boc-Cystamine*HCl

16

FNN1003

Fmoc-DAB*HCl

15

BNN1012

Boc-DAB*HCl

14

FNN1004

Fmoc-DAP*HCl

13

BNN1070

Boc-DAB-Bzl*HCl

14

FNN1030

Fmoc-DAP-N3

13

BNN1240

Boc-DADec*HCl

18

FNN1005

Fmoc-DAPe*HCl

16

BNN1260

Boc-DADod*HCl

19

FNN1040

Fmoc-DETA(Boc)-Suc-OH

5

BNN1210

Boc-DAHep*HCl

17

FNN1006

Fmoc-DODA*HCl

20

BNN1230

Boc-DANon*HCl

18

FNN1007

Fmoc-DOOA*HCl

20

BNN1220

Boc-DAOc*HCl

17

FNN1008

Fmoc-EDA*HCl

12

BNN1052

Boc-DAP

13

FNN1020

Fmoc-EDA-N3

12

BNN1013

Boc-DAP*HCl

13

FNN1009

Fmoc-HMD*HCl

16

BNN1014

Boc-DAPe*HCl

15

FNN1120

Fmoc-homoPiz*HCl

23

BNN1250

Boc-DAUnd*HCl

18

FNN1010

Fmoc-Paz*HCl

23

BNN1015

Boc-DODA

20

FNN1050

Fmoc-Ppd

22

BNN1016

Boc-DOOA

20

FNN1130

Fmoc-TEPA(Boc3)-DIG

7

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Product code

Product name

Page

BNN1310

Fmoc-TEPA(Boc3)-Suc

7

FNN1045

Fmoc-TETA(Boc2)-Suc-OH

7

FNN1011

Fmoc-TOTA*HCl

21

HNN1100

H-TETA(Boc2)-H

7

HNN1090

N3-Cystamine*HCl

17

BNN1150

N3-TOTA

21

NNN1001

Ns-DAP*HCl

14

NNN1004

Ns-DAP-Boc

14

NNN1003

Ns-EDA-Boc

12

PAA1170

Poc-Cystamine*HCl

17

SNN1190

Spermine(BBBB-CO2H) (S)

6

SNN1220

Spermine(BBBSuc)

5

SNN1200

Spermine(BHHB)

5

SNN1140

Spermine(FBBSuc-OH)

5

SNN1040

Spermine(HBBB)

5

SNN1080

Spermine(HBBH)

5

SNN1170

Spermine(HHHN3)*3HCl

6

SNN1130

Spermine(HHHStea)*3HCl

6

SNN1210

Spermine(N3HHN3)*2TsOH

6

SNN1240

Spermine(SucBBSuc)

6

BNN1300

TEPA(HBBBH)

7

TNN1000

Trt-DAB*AcOH

15

TNN1003

Trt-HMD*AcOH

17

ZNN1047

Z-DAB*HCl

15

ZNN1090

Z-DADec*HCl

18

ZNN1110

Z-DADod*HCl

19

ZNN1080

Z-DANon*HCl

18

ZNN1070

Z-DAOc*HCl

18

ZNN1000

Z-DAP*HCl

14

ZNN1001

Z-DAPe*HCl

16

ZNN1002

Z-EDA*HCl

12

ZNN1048

Z-EDA-EDA-Z

12

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Get in Contact Iris Biotech GmbH Adalbert-Zoellner-Str. 1 95615 Marktredwitz Germany

+49 (0) 9231 97121-0 +49 (0) 9231 97121-99 info@iris-biotech.de www.iris-biotech.de

Distribution Partners The list contains the current distributors of Iris Biotech in different regions of the world. The latest list of distribution partners and contact details is available at: www.iris-biotech.de/distribution-partner

China: Chengdu Yoo Technology Co., Ltd.

Japan: BizCom Japan, Inc. Shigematsu & Co., Ltd Cosmo Bio Co., Ltd.

USA & Canada: Peptide Solutions LLC

India, Bangladesh, Oman, Sri Lanka, United Arab Emirates: Sumit Biosciences Pvt Ltd.

Singapore, Thailand, Malaysia, Indonesia, Vietnam, Philippines, Brunei, Burma (Myanmar), Laos, Cambodia, Timor-Leste: SciClix Pte. Ltd.

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Empowering Peptide Innovation