Page 1

2 OH

O

O C OO -

6.3.2.7-10 6.3.2.13 HO O

2.4.99.7

OP C

OP P U

C H 3C H

2.4.1.17

NHAC

O C HOH C HOH C H 2 OH

HO

OH 2.7.7.43

1.1.1.158

C H 2 OH O

NHAC

C OO

O

UDP -N-A c G luc os amine pyruvate N-A c -Mannos amine-6-P C H 2 OH O

C H 2 OH O

HO OH HO OH

C H 2 OH O

HO OH

OH

UDP -G luc uronate

5.4.2.8

C H 2 OH O

4.1.3.20

AC NH HO OH OH

HO OH

Mannos e-6-P

5.1.3.14

UDP -N-A c -G luc os amine

OP

OH

OH

O OH H

OH OH

C

C

C

H

OH H

C OO -

C H

OH H

OH OH

C

C

C

H

H

C

H

HOC H 2

OH H

OH

C

C

C

H

CO

OH H HOC H 2

H

O

C

OH H

HOC H 2 C

H

OH H

OH

C

C

C

H

OH H

C HO

H

OH

C

C

C

4.1.1.34

OH H

H

C

C

C

H

OH OH

C

C

C

H

H

OH

C HO

OH H

H

C

H

HOC H 2

C

H

OH H

C

C

H C

P OC H 2

2.7.1.53

OH

C

C

H

OH

HOC H 2

OH H

C

C

HOC H 2

C

C

H

H

CO

OH H

2.7.1.47

1 .1 .1

.9

HOC H 2

C

HOC H 2

C

H

H

H

OH

C

C

C

C

C

CO

C

H

C

C

2e-

2e-

H+

H

P OC H 2 C

C

3.1.3.11

C HO

E rythros e-4-P P OC H 2

5.3.1.6 P OC H 2

.1 .1

H

OH

C

C

4.1.2.-

H

HO

C

C

C

D-Xylulos e-5-P

P OC H 2 C

H

C

C

C HO

P OC H 2

OH OH OH

H

H

H OH

C

C

C

P -R ibos yl amine C O C H 2O P

C

NADP+

HOC H 2 C OC H 2 OP

Chl.A0 P700

8

β β

2

CO2

1

H+

γ

2 2

H+

c

ATP α α

β

THYLAKOID MEMBRANE

ATP synthase

P -R ibos yl-P P

A DP

3.6.1.34

STROMA

HO

C OO

C OO

A rac hidonate

HO

L I P I D

C O-S -AC P

S tearoyl-C oA

5.3.99.5

T hromboxane B 2

OH-S tearoyl-C oA

P OC H2 C H(O P ) C OO

Oxos tearoyl-C oA

C H 3 (C H 2 ) 14 C OS C oA

C hain elongation

P almitoyl-C oA C H 3 (C H 2 ) n C H=C HC OS -C oA

1.3.1.9 2, 1.3.1.10

A C Y L -A C P

4.2.1.60 4.2.1.61

3-E noyl-A C P

Dec anoyl-A C P

1. 3. 1.

C H 3 (C H 2 ) 2 C H 2 C H 2 C OS AC P

C H 3 (C H 2 ) 6 C H=C HC OS AC P

4 .2 .1

2, 3-Dec enoyl-A C P C H 3 (C H 2 ) 2 C H=C HC O-S -AC P

1.3.1.9

Hexanoyl-A C P

4. 2. 1.

3, 4-Dec enoyl-A C P 9

N

4.2.1.59

2, 3-Hexenoyl-A C P C H 3 C H=C HC O-S -AC P

1.3.1.9

B utanoyl-A C P

6.2.1.3

A C Y L -C oA

F A T T Y A C ID

3.1.2.20

2.3 .1.1 5 C H 2 O-C O-R

3.1.1.3

C arnitine O-A c yl-c arnitine

C H 2 O-C O-R "

Diac yl

FAT

O-A c yl-c arnitine

2.3.1.20 glyc erol 3.1.3.4 2.7.1.107

3.1.1.28

2.3.1.39 C H 3 C H(OH)C H 2 C OO

4.1.1.4

.1 .2

C H 3 C O-S -AC P

3.1.2.11

(Mitoc hondria)

D E G R A D A T I O N

1.3.99.3

C H 3 (C H 2 ) 2 C H 2 C H 2 C OS C oA

Hexanoyl-C oA C H 3 C H 2 C H 2 C OS C oA

B utanoyl-C oA

C H 3 (C H n C H(OH)C H 2 C OS C oA

4.2.1.17

2, 3-E noyl-C oA

C H 3 (C H 2 ) 2 C H=C HC OS C oA

4.2.1.17

C H 3 C H=C HC OS C oA

4.2.1.55

1.3.99.3

2, 3-Hexenoyl-C oA

1.3.99.2

C rotonoyl-C oA

3-OH-A c yl-C oA

1.1.1.35

C H 3 (C H 2 ) 2 C H(OH)C H 2 C OS C oA

1.1.1.35

3-OH-Hexanoyl-C oA C H 3 C H(OH)C H 2 C OS C oA

3-Oxoac yl-C oA

2. 3. 1.

C H 3 (C H 2 ) 2 C OC H 2 C OS C oA

2. 3. 1.

3-Oxohexanoyl-C oA C H 3 C OC H 2 C OS C oA

1.1.1.157

3-OH-B utanoyl-C oA

Odd C F atty ac ids

C H 3 (C H 2 ) n C OC H 2 C OS C oA

1 .1

C H 3 C H 2 C H=C HC OS C oA

P entanoyl-C oA

C H 3 C H 2 C H(OH)C H 2 C OS C oA

NA D ATP C O2

16

16

P entenoyl-C oA

1.1.1.35

3-OH-P entanoyl-C oA

4.1.3.5

3-Oxopentanoyl-C oA

OH

C H 2 O-C O-R

OH

O

-

P HOS P HA T IDY L S E R INE

OH

P hos phatidyl inos itol

2.7.8.8

P hos phatidyl ethanolamine C E P HA L IN O

2.7.7.14

C DP -E thanolamine

L E C IT HIN

3.1. 1.5

-

(C 20)

2.5.1.10

(C oenzyme Q) 5.2.1.3

trans -R etinal

11-c is -R etinal

L ight

C HO

1.1.1.105

1.1.1.105

Menaquinone

P hytol

P las toquinone CH3

C H 2 OH

5.2.1.7

O

11-c is -R etinol

Dark

(V itamin A )

C H 2 OH

(V itamin K )

C HOL E S T E R OL

P regnenolone

N

CH N

Fe

HC H3C C H2

H 3C

CH

C H

C H2

C OO -

HE ME

N H

H2C

N

N C H3

H 3C C H2

C H2

C H2

C OO -

1.3.3.4 4.99.1.1

CH

H3C

N H

H

C H2

C H2

H C H2

C OO -

C H2

N

C H2

C H2

C H2

C H2

C OO -

P rotoporphyrinogen

C OO -

1.3.3.3

H C H2

- OOC

C H2

H 2C

C H2

C H2

N

C H3 -

C H2

S qualene (C 30)

C H2 C H2

C OO -

C OO -

4.1.1.37

H N C H2

C H2 C H2

C OO -

- OOC

C OO -

4.3.1.8 4.2.1.75

CH 2 CH 2

H 2C H 2C

C H2

Uroporphyrinogen

5-A mino-

C OO levulinate

TE

H2N

P orphobilinogen

H

H

C

C

C

A DP

Pi

ATP E ND

E R G O N IC R E

AαT

OH OH O

.4

H+

1 .2

.1 .1

1

+ C H 2 C H(NH 3 )C HO

HC

C

N

NH CH

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d-C MP

N

C ONH 2 NH C C HC N

C H2

HC

C

N

NH CH

O C

N R PPP

6.3.4.2

H+

Y

CH

A C T IO N

C H 2.7.4.6 CH

RPPP

C Y T IDINE triphos phate

.1 .2

6 .3 .2

9

N

C H3

4.2.1.9

(S A M)

HOC H 2 C (C H 3 ) 2 C OC OO

Oxopantoate

1.1.1.169 HOC H 2 C (C H 3 ) 2 C H(OH)C OO

P antoate ß-A lanine 3.5.1.22

1.2.1.25

C H3

6.3.2.1

HOC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C OO

P A NTOT HE NA T E 2.7.1.33

CH3

+ C H C H(NH 3 )C OO

C HC OC OO C H 3C H 2

2.6.1.32

P OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C OO

4-P -P antothenate C ys teine 6.3.2.5

C H 3C H 2

IS OL E UC INE CH3

C H3 C H 3 C H=C HC OS C oA

(C H 3 ) 2 C HC HC H(OH)C OO

(C H 3 ) 2 C HC H 2 C OC OO

3-Is opropyl- 1.1.1.85 Oxoleuc ine 4.2.1.33 malate

C OO P OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC HC H 2 S H

4-P -P antothenylc ys teine

1.2.1.25

C H 3 C H 2 C HC OS C oA

4.1.1.36 P OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC H 2 C H 2 S H

4-P -P antetheine

C H3 OOC C H 2 C = C HC OS C oA

6.4.1.4

3-Methylglutac onyl-C oA H C

HC OOC C

N

C H3 C H 3 C = C HC OS C oA

1.4.1.9

H2 C

H 2C OOC C

N

1.3.1.26

C arnitine

OOC C H 2 C H 2 C H 2 C OS C oA

2.7.1.24

C H2 C H-C OO

C oenzyme A

N 6 -T rimethyl3-OH-lys ine

2-Oxoadipate

OOC C H 2 C H 2 C H 2 NH 2

2. 7. 2.

1.

.7.1 1.7 .6.4 1.6 .1 .6 18 6.3.4.16 1.

2.5.1.16

P utres c ine

G lutamic s emialdehyde

CH

2.6.1.13

NO

HOC H H 2C

A rgininos uc c inate

+ NH 2

H 2 NC N(C H 3 )C H 2 C OO

C reatine

C HC OO

1.14.11.2

OOC C HC H 2 C OO N + H 2 NC NHC H 2 C H 2 C H 2 C H (NH 3 ) C OO

+ NH 2

2.1.1.2

4.1.3.16

4-Hydroxy2-oxoglutarate

NH

P R OL INE

2.7.3.2

HN C

P - HNC N(C H 3 )C H 2 C OO

P -C reatine 3.5.2.10

NH

N C H3

CO CH2

A mino A c ids B ios ynthes is Degradation

P urines & P yrimidines B ios ynthes is Degradation

V itamins C o-enzymes & Hormones B ios ynthes is

Degradation

+ OOC C H(OH)C H 2 C H(NH 3 )C OO

4-Hydroxyglutamate

C HC OO N H

1.5.1.12

P hotos ynthes is Dark R eac tions Human Metabolis m is identified as far pos s ible by black arrows

B ios ynthes is

Degradation

C OMP A R T ME NT A T ION

2.6.1.23

C H2

HY DR OXY P R OL INE

4.3.2.1

G uanidoac etate

C H2

C H2

1.14.13.39

OHC C OO

OOC C H(OH)C H 2 C OC OO

6.3.4.5

3.5.3.6

S ac c haropine

P entos e P hos phate P athway

P yrroline-5c arboxylate 1.5.99.8 C H2 1.5.1.2

A R G ININE 2

C H 3 C OC OO

P yruvate G lyoxylate

C HC OO N

2.1.3.3

NH 2

H 2 NC NHC H 2 C OO

B ios ynthes is Degradation

H 2 NC H 2 C H 2 C H 2 C H 2 NH 2

4.1.1.17

3.5.3.1

B ios ynthes is Degradation

L ipids

+ OHC C H 2 C H 2 C H (NH 3 ) C OO

+ H 2 NC ONHC H 2 C H 2 C H 2 C H (NH 3 ) C OO

+ H 2 NC NHC H 2 C H 2 C H 2 C H (NH 3 ) C OO

+ C H 2 C H 2 C H 2 C H 2 C H (NH 3 ) C OO

L E G E ND C arbohydrates

S permidine

1.2.1.41

2.1.3.3

G lyc ine +

S -A denos ylmethyl thiopropylamine

H 2 N(C H 2 ) 4 NH (C H 2 ) 3 NH 2

C H2 C H2

UR E A

C OO NH C HC H 2 C H 2 C OO

1.5.1.9

(Dec arboxylated S A M)

+

6.3.5.5

H 2 NC ONH 2

LY S INE

+ OHC C H 2 C H 2 C H 2 C H (NH 3 ) C OO

2-A minoadipate 1.2.1.31 2-A minoadipate s emialdehyde

2.5.1.22

11 P OOC C H C H C H (NH ) C OO 3 2 2

G lutamine

2.1.4.1

N 6 -T rimethyllys ine

A C I D S

+

S permine

+ H 2 NOC C H 2 C H 2 C H (NH 3 ) C OO

H 2 NC OO P

.7 5 .1 .1 20 4. 1. 1. 1.5.1.7 - 10

+ H 2 N(C H 2 ) 4 C H(NH 3 )C OO

C H 3 -S C H 2 C H 2 C HNH 2

H 2 N(C H 2 ) 3 NH (C H 2 ) 4 NH (C H 2 ) 3 NH 2

15

3.5.1.2 6.3.1.2

ATP C O2

1.14.11.8

2.6.1.39

N-S uc c inyl-2, 63.5.1.18 Diaminodiaminopimelate pimelate

A M I N O

A denos yl

(G A B A )

1.

OOC C H-C H 2 C H 2 C H 2 C HC OO + NH 3

OOC C HC H 2 C H 2 C H 2 C H-C OO + NH 3

+ + (C H 3 ) 3 N(C H 2 ) 3 C H 2 C H(NH 3 )C OO

+ OOC C H 2 C H 2 C H 2 C H (NH 3 ) C OO

4-A minobutyrate 4.

+ NH 3

OOC C H 2 C H 2 C ONH OOC C H 2 C H 2 C ONH OOC C OC H 2 C H 2 C H 2 C H-C OO

2.6.1.17

OOC C H 2 C H 2 C H 2 C OC OO

G lutaryl-C oA

Dephos pho-C oenzyme A

P -ADP - OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC H 2 C H 2 S H

(C H 3 ) 2 C HC H 2 C OS C oA

Is ovaleryl-C oA

+ + (C H 3 ) 3 N(C H 2 ) 3 C H 2 C H(NH 3 )C OO

1.14.11.1

ADP - OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC H 2 C H 2 S H

L E UC INE 1.2.1.25

1.3.99.10

3-Methylc rotonyl-C oA

C H2 C H-C OO

2.7.7.3

+ (C H 3 ) 2 C HC H 2 C H(NH 3 )C OO

2.6.1.6

2.5.1.6

S -A denos yl methionine

C H 2S H + OOC C H(NH 3 )C H 2 C H 2 C ONHC HC ONHC H 2 C OO

C H 3 C HC O-S C oA

C H3

C H 3 C H(OH)C HC OS C oA

2.1.1.10 2.1.1.20

G lyc ine

.3

3-Hydroxy- 4.2.1.17 Methyl 1.3.99.3 Is obutyryl-C oA Is obutyryl-C oA ac rylyl-C oA

C H 3C H 2

+ C H 3 S C H C H C H(NH )C OO 2 2 3 +

4.1.2.12

C H3 C H 2 = C C OS C oA

HOC H 2 C HC OS -C oA-

1.2.1.32

Adenos yl

2-Oxo- 1.4.1.8 V A L INE is ovalerate

C H3

3.1.2.4

ME T HIONINE

C H3 + C HC H(NH 3 )C OO C H3

2.6.1.32

2SO 4

G lutathione

HC HO C HC OC OO

C HC OO

+ C H 3 S C H C H C H(NH )C OO 2 2 3

6 .3 .2

4.2.1.19

NH

4.3.1.3

2.7.7.4

Adenos yl

C H3

CH

2.1.1.13 2.1.1.14

B ile A c ids

2.3.1.46

C (OH)C H(OH)C OO

C H 2 C OC H 2 OP

N

Imidazole ac etol-P

C

(A P S )

γ-G lutamylc ys teine

C H

Uroc anate

A denylyls ulphate

C H 2S H + OOC C H(NH 3 )C H 2 C H 2 C ONHC HC OO

.2

C H

NH CH

N

+ S C H 2 C H 2 C H(NH 3 )C OO

T aurine

C

HC

2.6.1.9

S -A denos yl homoc ys teine

HO 3 S C H 2 C H 2 NH 2

1.8.1.3

CH

C

OH OH HN

CH

Homoc ys teine

G lutamate

H C

Imidazole glyc erol-P

4.2.1.49

+ HS C H 2 C H 2 C H(NH 3 )C OO

4.4.1.8

H P OC H 2 C

RP

His tidinol-P

NH CH

2.7.1.25

4.2.1.22

C ys tathionine

C H3

2.6.1.19

1.4.1.14

N2

+ NH

C

N

P Y R I M I D I N E S

(C T P )

N N

C DP

NH 2

N OC

CH CH

C H 2 C H(NH 3 )C H 2 OP

Imidazolone propionate

P hos phoadenylyls ulphate

RP

1.17.4.1

C ytos ine

HN OC

C HC H 2 C H 2 C OO

OC

CH N

d-C DP

NH 2 C CH CH OC NH

CO

3.1.3.15

N C C

N

HOC H HC

C H2 C HC OO

N

3-Hydroxypyrroline5-c arboxylate

T he "B ackbone" of metabolis m involves G LY C OLY S IS in the C Y T OP LAS M, the T C A C Y C LE (mainly) in the Mitochondrial matrix and AT P F OR MAT ION s panning the MIT OC HONDR IAL INNE R ME MB R ANE

An electron flow (an electric current) generated from NADH and UQH2 drives the translocation of protons from the matrix to the intermembrane space. The retrolocation of these protons through the F0 subunits of ATP synthase to the matrix then supplies the energy needed to form ATP from ADP and phosphate

E lectron F low

P roton F low

1.5.1.2 S mall Numbers ( eg. 2.4.6.7) refer to the IUB MB E nzyme C ommis s ion (E C ) R eference Numbers of E nzymes

C reatinine

22 nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-A ldrich Product No. M 3907

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C

3.5.2.7

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H

C H 2 C H(NH 3 )C H 2 OH

C HC H 2 C H 2 C OO NH CH

2-3-Dihydroxy is ovalerate

+ (C H 3 ) 3 NC H 2 C H(OH)C H 2 C OO

NH 4+

F0

© 2003 International Union of Biochemistry and M olecular Biology

A rgentina SIGMA-ALDRICH DE ARGENTINA, S.A. Tel: 54 11 4556 1472 Fax: 54 11 4552 1698

H

O C

2.7.4.14

N

2.4.2.9

P OC H 2 C

His tidinol

1.1.1.23

C H3

1.1.1.86

+ OHC C H 2 C H (NH 3 )C OO

OR NIT HINE

s n it

HN H 2N C

NH 2 C CH N CH OC N DP

d-UMP

OH OH

C OOH

1.1.1.3

G L UT A MA T E

T IO N

β

H+ H+

6.3.4.1 6.3.5.2

1

CH CH N DP 3.5.4.12

.4

RP

NH

CH3

4.2 .1. 18

+ OOC C H 2 C H 2 C H (NH 3 ) C OO

F1

1 0 c -s ucb- u

2. 4. 2.

O C

P -R ibulos ylformimino P -R ibos ylformimino 5-aminoimidazole- 5.3.1.16 5-aminoimidazolec arboxamide-R P+ c arboxamide-R P +

Homos erine 2.7.1.39

C OOH

+ H 2 NC H 2 C H 2 C H 2 C H (NH 3 ) C OO

ε

NH 2 N OC C NH CH C HC N N

C (OH)C H(OH)C OO

2-Is opropylmalate

2-OXO A C ID NA

H+ H+ H+ H+

D P R OTONS

X

3

α

H+

α

4.2.1.24

N H

H

C

CH N RP

H

P U R I N E S

G UA NOS INE -P

3.5.4.1

CH OC N C H RP

N C C

N

2.7.4.8

HN OC

O C

HN

+ HOC H 2 C H 2 C H(NH 3 )C OO

C IT R UL L INE

γ

γ

a

A

N H

CH

RP

(G MP )

2.1.1.45

+ OOC C H 2C H 2 C OO C H 2 C H 2 C H(NH 3 )C OO

1.1.1.3

(C H 3 ) 2 C HC (OH)C H 2 C OO

ATP

P +1 P i

δ

CH2 H2NCH2C=O

C H2 C H2

Pi AD P + H+ H+ H+ β H+ H+

H2O

COOCH2

C OO C H2

N H

H

H 2C

OOC

C H2

C H2

H2 C

N H

H 2C

N

C oproporphyrinogen

C OO -

C H2

C H2

N H

H

H 3C

C H3

C OO C H3

H2 C

N H

H 2C

N

5.4.99.7 1.14.99.7

C OO -

C H2 C H3 C H 2

H2 C

L anos terol

C

N

Zymos terol

β

β

IV

1/ O 2 2

TR A NS L O

H 3C

CH

CH

H

6.4.1.3

C arbamoyl-P

AT P

G uanine

T HY MIDINE -P 2 .4 .2

CH N

XA NT HOS INE -P

.1

C -C H 3 CH DP

OC

(XMP )

2-Methylac eto-1.1.1.35 2-Methyl-3-4.2.1.17T iglyl-C oA 2 Methylbutyryl1.3.99.3 ac etyl-C oA hydroxyC oA butyryl-C oA

4.1.1.70

2.6.1.-

MI

NO 2 -

F1

2

HO

H

C OO -

C H2 C H3

H C

2H +

1.9.3.1

H

HO

Des mos terol

C HL OR OP HY L L

C H2 CH

H

HO

H

C H3

1.3.99.7

1.6.6.1 1.7.99.4

F6

2eH HO

N

CH CH

C -C OO OC N RP

4 .1

C OO

A s paragine

NO 3 -

ting A s por . 6 . 1 . 3 T P s y 4 nth 3 os cp

δ

2H+ C uB Heme a 3

P roges terone

CH C -C OO NH

Hypotaurine

G lutamyl-P

2H+

Heme a

S T E R OIDS

31

R -C O-C OO

n tra

C

.4 .9 HN

RP

N C C

O C

HN

1.1.1.205

3

.1

OOC C H 2 C H 2 C HO A s partyl 4.2.1.52 2, 3-DihydroP iperideineN-S uc c inylS emialdehyde dipic olinate 2, 6-dic arboxylate 2-amino-6-oxoS uc c inic pimelate s emialdehyde OH

1.4.1.2

2.5.1.21

(V itamin E )

1. 1. 1.

2-A MINO A C ID

_ UQ.

+-

O C

C ys teate

3-Hydroxyis obutyrate

+ R -C H(NH 3 ) C OO

C uA C uA

(C 15)

O C H3

α-T oc opherol

P hylloquinone

8

A s partyl-P

C yt.c

F arnes yl-P P

CH3

4.2.99.9

O C N

6.3.4.4

O

2 .7

Urac il

HN

+ HO 3 S C H 2 C H(NH 3 )C OO

C H3 HOC H 2 C HC OO

.3 .1

+ H 2 NOC C H 2 C H (NH 3 C OO

5-A minolevulinate

(C 20)

C H3

1.3.1.2

7 .4

C A T E C H O L A M I N E S

CH N

(IMP )

3.1.4.6

G DP

3.3.1.1

C H 3 C OC (OH)C H 3

4.2.1.18

5.4.99.2

Glycine

e

C H 2 OH

trans -R etinol

HO

OPP C H2

3. 5. 4.

N

C

INOS INE -P

2.4.2.1

1. 17 .4

O C

+ C H 2 C H(NH 3 )C OO + S C H 2 C H 2 C H(NH 3 )C OO

4.4.1.1

C Y S T E INE

C OO

UQ

1.10.2.2

A denylos uc c inate

.6

4.2.1.9 2-A c eto-22-Oxo-3-methyl 2: 3-Di-OHhydroxy- 1.1.1.86 3-methylvalerate valerate butyrate

1.2.1.16

as

O

2.3.1.76 3.1.1.21

S UC C INY L -C oA

1eC yt.bH

C yt.c 1 2UQ

(C 10)

G eranyl-geranyl-P P n

Ubiquinone

O

C HO

1.2.1.36

2.5.1.1

C H 3 C = C HC H 2 C H 2 C = C HC H 2 O P P C H 2O P P

5

A s partate

2.7.4.6

2.4.2.4

HN OC

O C

A C I D S

F ormylamidoimidazolec arboxamide-R P HC

(P A P S )

2-A c etolac tate

5.1.99.1

2H+ 1e-

3. 1. 3.

O C C

3.5.4.10

OC

C H2 C H2 NH

1.8.99.2

C H 3 C H 2 C OC OO

-OOCCH2CH2COO-

S UC C INA T E

UQH 2

2e- 2UQ _. III 2eF e-S C yt.bL

G eranyl-P P

C H3

C H 3O

4H+

18

6.3.5.4 -OOCCH2CH2CO.SCoA

H2N HC O

NH

2.4.2.1

d-G DP

T DP

His tidinal

HS O -

1.8.99.1

+ P OOC C H 2 C H (NH 3 )C OO

4.3.1.1

2.3.1.37

2UQH 2

2 .7 .2

1.2.4.2 2.3.1.61

2H+

1.10.2.2

C H3

CH3

AS PAR TATE

A

R etinoate

(C 5)

2.5.1.29

O C H 3O

Ops in

C OO -

R etinol es ters

C H 3 C = C HC H 2 O P P

1.1.1.23

O-P hos pho4.2.99.2 homos erine

C H3

NS

1.13.11.21

R hodops in

(C 5)

CH

+ P OC H 2 C H 2 C H(NH 3 )C OO

Methylmalonyl-C oA

4.1.1.71

TR A

Metarhodops in

C H 3 C -C H 2 C H 2 O P P

Is opentenyl-P P

Inos ine

2

NH

2.4.2.15

.7 .6

HO 2 S C H 2 C H 2 NH 2

16

1.1.1.41

C H2

Dimethylallyl-P P

2.5.1.32

II

3. 2. 2.

CH

4.3.2.2

T hymine

C

HC N

C ys teine s ulphinate

C H 3 C H 2 C OS C oA

G L UT A R A T E

UQH 2

C H3

(C 40)

hv

(C 40)

UQ 4.1.1.33

C C

1 .1

3.5.4.19

NH

+ .8 HS C H 2 C H(NH 3 )C OO

4.2.1.16

2.1.3.1 4.1.1.41 5.1.99.1

6.2.1.4

F AD

RP

P ropanoyl-C oA

-

2-OXO -

+

N

N

F umarate

O C

P OC H 2

+ C H 2 C H(NH 3 )C OO

C CH

HS .9 9

OOC -C H-C OS C oA

1.3.5.1

F e-S C yt.b

NHC OR

C erebros ide

P hytoene T o B rain -V IS ION

ß-C A R OT E NE

Diphos phomevalonate

C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 O- G alac tos e

C H-C OO

C H 3 C OC HC OS C oA

-OOCCOCH CH COO2 2

F ADH 2

N

UR IDINE Dihydro Orotate Orotidine-P Uridine-P UDP 4.1.1.23 (UMP ) 2.7.4.4 2.4.2.10 2.7.4.6 triphos phate orotate 1.3.1.14

C H3

OOCCH=CHCOO-

P s yc hos ine

3.2.1.46 2.4.1.47 1.3.99.7

4.1.3.1

CH

C

H 2N

2.1.2.3

1.13.11.20

CH2COOC(OH)COOCH2COO-

CH(OH)COO CHCOOCH2COO-

N C

H 2N

RP

P lant P igments

HN

2 .7

HN OC

Oxobutyrate

2. 3. 1.

F UMA R A T E

UQH 2

C H 3 C (OH)C H 2 C H 2 O P P

A c yl-C oA

52

4.2.1.3

or 2H+ -

C H 2 C OO

+ NH 3 C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 O- G alac tos e

UDP -G alac tos e

C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 OH

C eramide

C HOL INE

2.7.1.32

Malonic s emialdehyde

IS OC IT R A T E

MA L A T E 4H+ 2H+ 4.2.1.2

2.7.1.36 2.7.4.2

+ HOC H 2 C H 2 N(C H 3 ) 3

+ OC H 2 C H 2 N(C H 3 ) 3

C holine-P

2.4.1.23 3.5.1.23

(C 40)

HE MOG L OB IN

P O R P H Y R I N S

4-S phingenin

3.1.4.12

L yc opene

3.1 .4. 12

NHC OR

2.7.8.3

2.3.1.6

1.

CH3CH(OH)CH2CO.SCoA

1.6. 5.3

Mevalonate

.4 .2

2.

2.6.1.1

Glyoxylate Cycle

2H

2F e -S (5 C lusters)

4H+

HC

NH

F ormimino glutamate

1.6.4.1

C IT R A T E 1.1.1.37

O C

CH

N

NH N C C N CH C HC NH R P N

C C H3 CH NH

HN

C Y S T INE

Methylmalonyl s emialdehyde

-OOCCHO

F MNH 2

HN

CH

d-C T P GTP T T P 2.7.4

OOC

4 .2

4 .1

4.1.3.8

4.1.3.2

T annins

4.3.1.3

C H 2 C H 2 NH 2

4.1.3.7

I

L IG NIN

OOC -C H-C H 2 C OO

O C

HIS T A MINE

+ S -C H 2 C H(NH 3 )C OO + S -C H 2 C H(NH 3 )C OO

C H3 OHC C HC OO

AD

S T E R O I D S

.3

2.4 .1. 62

S P HING OMY E L IN

I S O P R E N O I D S

2 .7 .8

UDP -S ugars A c yl-C oA

G anglios ides

2.7.7.15

C DP -c holine

1.1.1.102

NHAcyl O + C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 O P O C H 2 C H 2 N(C H 3 ) 3 O

C H 3 C (OH)C H 2 C H 2 OH

3.1.4.3 + C P P -O C H 2 C H 2 N(C H 3 ) 3

+ NH 3 C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 OH

S phinganin

3 .1

3.1.4.4

2.7.8.2

+ NH 3 C H 3 (C H 2 ) 14 C H(OH)C HC H 2 OH

3

C H 3 (C H 2 ) 14 C OC HC H 2 OH

Dehydros phinganin

A c etylc holine

G lyc erophos phoc holine

C H 2 C OO

C H2

NH

O C

N C C

Dihydrourac il

3.5.2.2

C H 3 C OC (OH)C H 2 C H 3

18

C

H 2N

d-G T P

1.3.1.2

NH

4. 1. 3.

OHC C H 2 C OO -

4.1.1.32

OX A L OA C E T A T E

+

1.1.1.32

C H 3 C OC H 2 C H 2 N(C H 3 ) 3

C H

T HR E ONINE

1.2.1.18

-OOCCOCH COO2

I C H 2 C OO

Mevaldate

E thanolamine

C H 2 OH + C H 2 OP O C H 2 C H 2 N(C H 3 ) O

O C

4.1.1.29

GTP

NAD+

F MN

C H 3 C (OH)C H 2 C HO

+ HOC H 2 C H 2 NH 3

HOC H O

- L ys olec ithin

1.1.1.34

Oxalate

1.4.3.8

2.7 .1. 82

E thanolamine-P

C H 2 O-C O-R

+ C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 2.1.1.17 O C H 2 OC H=C HR 2.1.1.71 C H 2 O-C O-R R -C O-OC H O 3.1.1.32 O R '-C O-OC H + + C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 O O

2.3.1.50

+ P OC H 2 C H 2 NH 3

HOOC -C OOH

HOC H 2 C HO

4. 2. 1.

OH

T HY R OXINE

RP

.7 .6

OC

HIS T IDINE

1.1.1.39

NA DH+H +

ß-OH-ß-Methylglutaryl-C oA

G lyc ol aldehyde

OP hos phatidylglyc erol

HOC H O

C holine plas malogen 1.3.1.35 S erine +NH

1.2.1.21 2.7.8.5

O

C H 2 O-P O C H 2 C HOHC H 2 OH

-

+ C P P - OC H 2 C H 2 NH 3

2.7.8.1

G lyc olate

N

+ C H 3 C H(OH)C H(NH 3 )C OO

2.6.1.18

2.6 .1.4 4

4.1.3.4

C H 3 C (OH)C H 2 C OS C oA

1.6.5.3

C ardiolipin

O + C H 2 O P OC H 2 C H 2 NH 3

HOC H 2 C OO

C H 2 O-C O-R

C H 2 O-P O C H 2 C H(OH)C H 2 O-P -OC H 2 O O

R '-C O-OC H

1.2.3.5

C DP -diac yl glyc erol

R '-C O-OC H

O HC O-C O-R

4.1.3.5 C H 2 C OO

1.1.1.79

O

Inos itol

2.7.8.11

OHC C OO

G lyoxylate

2.7.7.41

O

C H 2 O P OC MP

S erine

C H 2 O-C O-R ’

C H 2 O-C O-R R '-C O-OC H O

4.1.1.65

R '-C O-OC H

C OO O + C H 2 O P O C H 2 C HNH 3 O

HO OH

C H 2 O-C O-R

C H 2 O-C O-R

R '-C O-OC H

1.3.99.7

C oumarate

I

S uc c inylhomos erine

A C E T Y L -C oA

NAD+

H

C H 2 O-C O-R

HOH GDP C O2

1.2.4.1 2.3.1.12 3.1.3.43

C H=C HC OO

OOC -C H-C H 2 C OO HNC O C N

.7 .7

HN OC

P -R ibos yl-A MP

4.1.2.5

4.1.1.12

7

4.

6.4.1.1

2.6 .1.4

C H 2 O-P O

.1 .2

18

LACTATE

NADH+H+

C H 3 C H 2 C OC H 2 C OS C oA

3.6.1.31

HC

HO 2 S C H 2 C OC OO

C H 3 C H(OH)C OO

CH3COSCoA

C H 3 C H 2 C H 2 C H 2 C OS C oA

R '-C O-OC H O

A L A NINE

4. 1. 3.

CH3COCOO-

2.3 .1.9

A c etoac etyl-C oA

2 .7

C H-C H 3 CH2 NH

3-S ulphinyl pyruvate

+ C H 3 C H(NH 3 )C OO

2.6.1.2

P Y R UV A T E C H 3 (C H 2 ) n C H=C HC OS C oA

I

I

ME L A NIN

2. 7. 7. 7 2.7.7.6

+ HO 2 S C H 2 C H(NH 3 )C OO

HS O 3-

1.4.1 .1

1.2.4.1 2.3.1.12 1.8.1.4

2.3.1.38

C innamate Menaquinone 1.14.13.11

T yramine

O

NH

O

2.7.7.7

NH 2 N + C C N CH C HC N N R P (P P )

4.4 .1.1 5

4.4 .1. 15

4.1.1.9

A c etyl-A C P

C H 3 (C H 2 ) n C H 2 C H 2 C OS C oA

A C Y L -C oA

C

C arnos ine

H

.1 .1

P Y R UV A T E

Malonyl-C o-A

1.1.1.30

A c etoac etate

P hos phatidate

3 .7

ATP

HOOC C H 2 C O-S C oA

C H 3 C OC H 2 C OO

C H 2O P

H

C

2.7.1.40

K E TONE B ODIE S

2.7.8.5

R ’-C O-OC H

C H 2 OH

Malonyl-A C P

2.3.1.41

C H 3 C OC H 3

4 .1

HOOC C H 2 C O-S -AC P

A c etone 3-OH-B utyrate

C H 2 O-C O-R

C H 2 O-C O-R R ’-C O-OC H

R ’-C O-OC H

T riac ylglyc erol

A DP

C H 3 C OC H 2 C OS AC P

3-P -G lyc erol

H

C

A c etyls erine

A c etaldehyde

P

L I P I D

2.7.1.30

H

C

+ C H 2 C O-OC H 2 C H(NH 3 )C OO

HS

C H 2O P

2.3. 1.51

0

C H 3 C HO

P -enolpyruvate

A c etoac etyl-A C P

1.1.1.8

HOC H

G lyc erol

(C ytos ol)

2.3.1.7

C H 2 OH

C H 2 OH HOC H C H 2 OH

.1 .3

1.1.1.1 C H 2 =C (O P ) C OO

3-Oxo-Hexanoyl-A C P

1.1.1.100

3-OH-B utanoyl-A C P

R -C H 2 C OO C H 3 (C H 2 ) n+2 C OS -C oA

2 .3

2.1.3.2

2.3.1.41

C H 3 C H(OH)C H 2 C OS -AC P

4.2.1.58

C rotonoyl-A C P

H

4.1.1.22

E T HA NOL

3-Oxo-Dec anoyl-A C P

1.1.1.100

3-OH-Hexanoyl-A C P

I

C H=C HC OO

OH

OH

NH

C H 3 C H 2 OH

C H 3 (C H 2 ) 2 C OC H 2 C OS AC P

C H 2 C H 2 NH 2

5

A denine

C arbamoyl ß-alanine

C C H 2 C HC OO NH NHC OC H 2 C H 2 NH 2

C

N

1.2.1.4

3-Oxoac yl-A C P

2.3.1.41 C H 3 (C H 2 ) 2 C H(OH)C H 2 C OS AC P

C

HC

2-P -G lyc erate

C H 3 (C H 2 ) 6 C OC H 2 C OS AC P

1.1.1.100

3-OH-Dec anoyl-A C P

.1 .2

(A MP )

Dihydro thymine

3.5.2.2

3.5.2.3

OH OH O

G lyc erate

2.3.1.41

60 C H 3 (C H 2 ) 6 C H(OH)C H 2 C OS AC P

.6 0

C H 3 C H=C HC O.S -AC P

C H 3 C H 2 C H 2 C OS AC P

1.1.1.100

3-OH-A c yl-A C P

O

A DE NOS INE -P

O C

HN OC

HN OC

P -R ibos yl-A T P

2.4.2.17

HOC H2C H(O P ) C OO

Mitoc hondrial

A DP

H 2 NC ONHC H 2 C H 2 C OO

3.5.1.6

ACE TATE

C H 3 (C H 2 ) n C OC H 2 C OS AC P

4 .1

Ubiquinone

1.1.1.204 1.1.3.22 Hypoxanthine 1.1.3.22 Xanthine

2.7.4.3 2.7.4.4

4.2.1.51

A M I N O

P henylpyruvate

(UT P )

P OC H 2

P -Hydroxypyruvate

4.2.1.11

C H 3 (C H 2 ) 5 C H=C HC H 2 C OS AC P

C H 3 (C H 2 ) 6 C H 2 C H 2 C OS AC P

C H 3 (C H 2 ) n C H(OH)C H 2 C OS AC P

1.3.1.13

NH 2 N C C CH C HC N R P (P ) N

HN

13

C H 3C OO

E ndoplas mic R etic ulum C H 3 (C H 2 ) 14 C OS -AC P

P almitoyl-A C P

. 1.

2.6.1.22

HOC H2C H(OH) C OO

5.4.2.1

P rephenate C H 2 C OC OO

2.6.1.5 4. 3. 1. 5

P HE NY L A L A NINE

N

R NA

H

HC

2, 3-Diphos phoglyc erate

C H 3 (C H 2 ) 14 C OC H 2 C OS -C oA

C H 3 (C H 2 ) 14 C H(OH)C H 2 C OS -C oA

Dehydros tearoyl-C oA

OH

OC

NH

2 .7

ß-Ureido is obutyrate

C arbamoyl as partate

2.6.1.52

2.7.1.31

OH

+

O

O C

2-A mino muc onate

A R O M A T I C

1.3.1.13 1.14.16.1

CH

HN

DNA

.7

2.7.7.6

2 C H2 OC C H-C OO N

P OC H 2 C OC OO

C H 3 (C H 2 ) 14 C OC H 2 C OS -C oA

B I O S Y N T H E S I S

P H O S P H O L I P I D S

OH

5.4.99.5

C horis mate

NH 2

OOC OOC C H 2 C OC OO

4.1.3.27

OC -C OO

1.1.1.29

1.1.1.95

3-P -G lyc erate

C OO O

HO

P ros taglandin P G E2

C H 3 (C H 2 ) 14 C H=C HC OS -C oA

C OS C oA

C OO

HO

P almitoleoyl-A C P

Oleoyl-C oA

1.14.99.5

P OC H2C HOH C OO

OH

2. 1

-OOC NH

P hos phos erine

ATP

C OO

L eukotriene B 4

O

5. 1 .1 3 . 9 9 4 .9 . 3 9 .1

1.3.1.35 C OS C oA

1.13.11.34

3.5.1.6

H 2 NC H 2 C H 2 C OO

+ P OC H 2 C H(NH 3 )C OO

C OO

γ-L inolenate

1.14.99.25

L inoleate

4.1.1.11

3.1.3.3

Hydroxypyruvate

A DP

1.14.12.1

NH 2

A nthranilate

C H 2 C H(NH 3 ) C OO

O

1.17.4.1

C H3

ß-A lanine

HOC H 2 C OC OO

2.7.2.3

CHLOROPLAST OUTER MEMBRANE

CO

UR A T E CH N

H 2 NC ONHC H 2 C HC OO

4.2.1.22

S E R INE

2.6.1.51 1.4.1.7

N H

20

3-A minois obutyrate

+

HOC H 2 C H(NH 3 )C OO

OH OH

4. 2. 1.

C H3 H 2 NC H 2 C HC OO

C HOL INE

1: 3-bis -P -G lyc erate

OP OP

ATP

4.1.2.5

+ HOC H 2 C H 2 N (C H 3) 3

P OC H 2C HOHC OO P

2.7.6.1

ATP

ATP

H+

C H 2O P O

Fixation

3

H+

THYLAKOID LUMEN

β2

α

εε

H+

H+

2.1.2.1

B etaine aldehyde

NA DH

C C

N

2.7.4.6

ATP

4.6 .1. 1

C

OH OH

2 .7 .7

F OL IC A C ID C1 P OOL

+

1.2.1.12 1.2.1.13

NH 2 N

2.7.4.6

1.1.99.1

Glyceraldehyde Pi

A DP

1.7.3.3

HC

d-A DP

OHC C H 2 N(C H 3 ) 3

Pi NA D+

+

HN

N

NH

d-A T P

1.2.1.8

2.4.2.14 6.3.4.7

Pi

Ribulose-1,5-bis-P

α

a

H+

H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ Protons from Water H+ H+ H+ H+ H+ H+ H+ H+ H+ H+

ADP α α 1

H+ H+

H+ PC PC

4H +

Translocated protons

Pi

.1

.1 5 .3 .1 2.7.1.28

(G lyc erone-P )

NADPH+H+

2PQ

OH

C yc lic A MP 1.4.4.2

B etaine

3-P -G lyc eraldehyde 5 .3 .1

OC

-O P ~O P ~O P O C H 2 O O O O

+

2.2.1.1

NH

N

OOC C H 2 N(C H 3 ) 3

Dihydroxyac etone-P

H+ H+

HN

O

O

2.1.1.5

S edoheptulos e-P P

O

NH CO

A llantoin O

N

O

1.5.99.2

3.5.2.5

CH

N C H2 O

O

C N H H

NH

HC

P

OC

OC

Dimethylglyc ine

2.2.1.1

H+

O

S arc os ine

OH OH OH H

D-R ibos e-5-P

O

OOC C H 2 N(C H 3 ) 2

4.1.2.13

2.4.2.18

C H2

S hikimate-5 4.6.1.4 enolpyruvate 3-P

N C C

H2N

RP

1.2.1.32

C OO

OOC

OH

+ C H 2 C H (NH 3 ) C OO

CH N

2.5.1.19

1.14.16.2

OOC

N

HC C

N

N

2. OOC C H 2 NHC H 3

G lyoxylate

C N H H

NH 2

.1 .4 2 .6 .1 0 .1 20 1 .4 1. 1.

NH 2

H 2N

RP

H2N

A llantoate

+

C H 2 (NH 3 )C OOH

C H 2O P O

NH

NH 2 CO

C OO

OC

G LY C INE

OH OH H

H 2N

Urea

6.3.4.13

C O C H 2O P

O

N-(5-P -R ibos yl) anthranilate

C H 2 C H (NH 3 ) C OO

T Y R OS INE

1.14.18.1

P las toquinone

C HO

HN

RP

3.5.3.4

F ruc tos e1: 6-bis -P

2.2.1.2

OH H

5

H

O

Dopaquinone

NH H 2C C

C HO NH

H 2 NC ONH 2

OH OH H C O C H 2 OH

C H C H 2O P

6.3.5.3 6.3.3.1 F ormyl F ormyl 5-A mino 4.1.1.21 5-A mino-4-imidazole 6.3.2.6 5-A mino-4-imidazole 4.3.2.2 5-A minoimidazole c arboxylate-R P (N-s uc c inylc arboxamide)-R P c arboxamide-R P glyc inamide-R P glyc inamidine-R P imidazole-R P

G lyc inamideribos yl-P

A DP

C

O-C -C OO

OH

OH

H2 C C H-C OO + NH 3

O

(V itamin E )

OC H NH 2 C OO

NH 2

C OO

Dopa

1.14.18.1

NH OC

OH

OC H 3

P O

2.6.1.5

OH

4.1.1.28

α-T oc opherol

OH

2.7.1.11

OH OH

H+

A1

Fe-S 2e- Cyt.f

H

C OO

OH OH

4.1.1.48

+ C H 2 C H (NH 3 ) C OO-

Dopamine

C HOHC H 2 OH

OH

S hikimate-3-P PEP

OH

OH

4-OH-3-Methoxyphenylglyc ol

2.1.2.2

2.7.1.71

C H 2 C H 2 NH 2

.1 .6

(Normetadrenaline)

H 2C OH

C

C OO

OH

Hydroxyphenyl pyruvate 1.3.1.13

(Noradrenaline)

2 .1

OC H 3

NHC OC H 2 NH 2

OH

P O

S hikimate

1.13.11.27

1.14.17.1

Norepinephrine

C HOHC H 2 NH 2

C O C H 2 OH

ATP

5.1.3.1

C HO

2 .7

8

2e-

C

2.7.1 .17

Fe-S

PC

Mn

HO

C

OH OH H

C O C H 2 OH

D-R ibulos e-5-P

3 3

._

2PQ

H

C H 2O P O

F ruc tos e-6-P

OH OH

C

H P OC H 2 C

1 .4

OH

OH

OH

Normetepinephrine .3 .4

NH

H

C H 2 C OC OO

OH

OH

4-OH-3-MethoxyD-mandelate

P OC H 2C HOHC HO

2e-

2PQH2

2.2.1.1

D-R ibos e

OH

OH

NA DP H

1.1.1.25

Dehydros hikimate

C HOHC H 2 NH 2

OH

OC H 3

5.3.1.9

5.3.1.8

1.1.1.44

H

OH

NADP +

HO

OH

OH

(A drenaline)

C H(OH)C OO

HO OH

NADP +

P OC H 2

H

H

.1 7

5.1.3.1

5.1 .3. 4

PQ

1e-

C C OO -

C H 2O P

C H 2 OH

C H 2 OH

*2e

Cyt bc

P680 Chl.a

O2

C

C

.1 3 .1

G luc os e-6-P

P -G luc ono lac tone

OH

O

C H 2 C OO

O C H 2 C OO

2.1.1.28

E pinephrine

C H 2 OP O

OC H

C OO

OH

OH

A DP

1.1.1.49

OH

OH OH H OH 6-P -G luc onate NA DP H

H

Cyt bf

PQH2

H+

C

OH H

PHOTO- H+

2e-

1e-

Pheophytin

H+

HOC H 2 C

H

2.6.1.16

HO OH

4

4.2.1.10

Dehydroquinate

O

C OO

OH

2.7.1.2 2.7.1.1

O

. 1.

OH OH OH

C H 2 OH

CO

2. 7

w

.

_ PQ

PQH2

QB

H 2O

OH

C

HOC H 2 C CO

C H 2 OH

OH

H

H

Ferredoxin

PQ

2eQA

H

OH

C

C

H

c otophosphoryla SYSTEM n-cycli electr 2H+ yclic Ph tion l No (electric curre on fl C nt) o H+ 2H+

PHOTOSYSTEM II

P H O T O S Y N T H E S I S

H

R ibitol

C HO

OH H

H+

C

OH OH OH

D-Xylulos e H+

H+

C

OH OH H

S orbitol

F ruc tos e-1-P

OH OH P OC H 2

HOC H 2 C

OH

C HOHC H 2 NHC H 3

ATP

3.1.3.9

C H 2O P O

CO

5.4.2.2

21

C OO

C OO

1-(o-C arboxy phenylamino) 1-deoxyribulos e-5-P

C OO

F umaryl 5.2.1.2 Maleyl 1.13.11.5 Homogentis ate ac etoac etate ac etoac etate

G L UC OS E

3.2.1.48

1. 1. 1.

2.7.1.3

H

D-Xylos e

C O C H 2 OH

OH H

1.10.2.1 1.10.3.3

CO

H

L -R ibulos e 2.7.1.16 L -R ibulos e-5-P

L -L yxos e

H

1.1.1.14

O

C H 2 OH

C

3.2.1.26

C OO

OH

O

4.6.1.3

O C H 2 C OO

-OOC OH

HO OH

H

Quinolinate

(ME L A TONIN)

C H2

OH

O

C H 2 OH O

N

C OO

N

NH

N-A c etyl-5-O-methyl-s erotonin

4.1.1.45 3-Hydroxy 1.13.11.6 2-A mino-3-c arboxy 2-A minomuc onateanthranilate muc onate s emialdehyde 6-s emialdehyde C OO H H C atec hol

3.7.1.3

C OO HOC -C H(OH)C H(OH)C H 2 OP CH N

C -C H(OH)C H(OH)C H 2 O P CH

2.4.2.19

C OO

C H 2 C H 2 NHC OC H 3

NH 2

OH

Quinolinatenuc leotide

2.4.2.19

C H 3O

2.1.1.4

N-A c etyl-s erotonin

NH 2

OH

Indole-3-glyc erol-P

C OO

NH

2.3.1.5

C OO + C OO N RP

N

Nic otinatenuc leotide

C H 2 C H 2 NHC OC H 3

+ C O C H 2 C H(NH 3 )C OO

+ C O C H 2 C H(NH 3 )C OO NH 2

4.2.1.20

T R Y P TOP HA N HO

3-Deoxy-D-arabinoheptulos onate-7-P

HO

NH 2

4.1.1.28

HOC H HC OH C

H

NH

5-Hydroxytryptamine

K ynurenine 1.14.13.9 3-Hydroxy kynurenine

+ C H 2 C H(NH 3 )C OO

C OO OC P OC H 2 C H 2

OP P U

OH

HO

C H 2 C H 2 NH 2

11

2. 4. 2.

R ibos e- P

2.7.7.18

C OO

NIC OT INA T E

+ N

-Adenos ine

O

Des amino-NA D

1.13.11.11

NH

NH

T ryptamine

OH

G luc os amine-6-P

S UC R OS E

H

OH OH H

H

OH OH

C HO

OH OH

C

C H 2 C H 2 NH 2

UDP -G alac tos e

G luc os e-1-P

OH

5.5.1.4

CO

2.7.1.47

CO

4

2.4.1.22

OH

C H 2 OH O

HO 5.1.3.2 2.7.7.10

OP

HO OH

HO OH

5.3.1.8

OP

OH

2.7.7.12

C H 2 OH O

Indolepyruvate

C OO

O

-O-P -O-P -O O

(S E R OTONIN)

3.5.1.9

F ormylkynurenine

HO

4.1.1.28

+ C O C H 2 C H(NH 3 )C OO C HO NH

4.1.99.1

NH

OH

P OC H 2

L -Xylulos e-5-P

C H 2 OH

Xylitol

.1 .4

C

C O C H 2 OH

D-R ibulos e

C H 2 OH

C

OH H

1.1.1.10

5 .3

L -A rabinos e HOC H 2 C

CO

OH

L -Xylulos e

OH OH H

C

OH OH

2.4.1.13

2. 3. 1.

C H 2 OH

F ruc tos e

OH H

C

CO

Dehydroas c orbate

H

OH H HOC H 2 C H

C H 2 OH

C

H

HOC H 2 C

5.3.1.3

D-A rabinos e

L -A rabitol HOC H 2

C HO

C

O

HOC H 2

2, 3-Dioxogulonate

H

C

A S C OR B A T E

C O C OO -

CO

OH

OH OH H

L -Xylos e HOC H 2

HOC H 2

C

H

1.1.1.130

3-Dehydrogulonate HOC H 2

HOC H 2 C

OH

C

2.7.7.9

C H 2O P O

2.4.1.9

Inos itol-P

OH H

OH H

C C OO -

CO

OH

H

P E N T O S E S

OH

C

H

C

2.7.7.27 2.7.7.34

OH OH

H

O

G ulonolac tone 1.1.3.8 2-Oxogulonolac tone 1.1.1.45

H

HO

OH OH H

OH

3.1.3.25

Inos itol

CO

HOC H 2

HO OH OH

1.13.99.1

G luc uronate

CO

OH NHC OC H 3

OH OP

HO OH

OH OH

1.1.1.19

G ulonate 3.1.1.18 HOC H 2

OH

OH

HO OH

OH

N-A c -G luc os amine-6-P

2.7.7.23

C OO

HOC H 2

HO

NHC OC H 3 5.4.2.3

N-A c -G luc os amine-1-P

HO

OP P U

UDP -G luc os e G alac tos e-P

2.7.7.24

HO OH HO OH

C H 2O P O

HO OH

OP P U

NHAC

1. 1. 1. 22

T DP -G luc os e

C H 2O P O

2.7.1.60

N-A c -Mannos amine

4.2.1.46

2.7.1.7

HO OH HO O P

5.1.3.6

OP P U

HO OH

1.14.16.4

C H 2 C OC OO

C H 2 OH O

2.7.1.6

NH

5-Hydroxytryptophan

Indole

4.1.1.43

G A L A C TOS E

C H 2OH O OH

G DP -G luc os e

MA NNOS E

2.7.7.13

Mannos e-1-P

5.1.3.7

3.1.3.29 AC NH 4.1.3.20 HO OH OH

OP P U OH

UDP G alac turonate

C OO

A DP G luc os e

OH

G DP -Mannos e OH

UDP -N-A c G alac tos amine

OP P U

OH

OP P T

OH

T DP -4-Oxo6-deoxygluc os e

+ C H 2 C H(NH 3)C OO

NH

NH

Indoleac etaldehyde

3.2.1.23 2.7.1.38

OH

19

C H 2O P O

HO

NHC OC H 3

5.1.3.13 O C H 2 OH O

C H 2 C HO

C H 2OH O

2.4.1.11 HO 2.4.1.21

2.4.1.1 etc.

OH

2.4.1.33

HO OH HO OP P G

O

L A C TOS E 2.4.1.21

O

1.

HO O C H2 C

C H 2 OH O

4.2.1.47 C OO -

C H3

R ibos e

6.3.5.1 6.3.1.5

NA D( P ) HO

4.

N-A c -Neuraminate (S ialate)

H E X O S E S

5.1.3.12

OP P U

OH

3.1.3.29 HO

C H 2 OH O C OO

T DP -R hamnos e

G DP Mannuronate

OH

(A uxin)

1.2.3.7

OH

O

O

O

N

Adenos ine(P )

-O - P - O - P - O-

+

Indoxyl

+

O

O

R ibos e

NH

Indoleac etate OH

OH

+

N

OH

NH

O OH

2.4.1.29

OH OH

HO OP P G

HO

C H 2 OH O

OH OP P T

G DP -F uc os e

2.4.1.16

C OO

HO C H 3

O C H3

OH

UDP -N-A c -Muramate

1.1.1.132

2.4.1.68 2.4.1.69 OP P U

OH

UDP Iduronate

C OO-

HO

C MP -N-A c etyl neuraminate AcNH

HO

C H 2 C OO C H 2 OH O

HO

O

C OO

C ONH 2

G LY C OG E N

.5

C OO -

C H 2 OH

B L OOD G R OUP A L G INA T E S O-A NT IG E NS S TAR CH S UB S T A NC E S P E C T IN INUL IN C E L L UL OS E

DE R MA T A N

C HONDR OIT IN

3. 5

C HIT IN

O

C HOH C HOH

AcNH

P E P T IDOG LY C A N C H

6.

HY A L UR ONIC A C ID

G LY C OP R OT E INS G A NG L IOS IDE S MUC INS

1.

P O L Y S A C C H A R I D E S

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metabolic pathway  

complete cellulars metabolic pathways

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