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CHEMISTRY AT THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

Fall 2017


CHEMISTRY AT THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

Professor Jillian Dempsey has had a banner year. Read about her on page 14.

Department Chair Jeffrey Johnson A Ronald Gallant Disinguished Professor jsj25@email.unc.edu Associate Chair Ralph House, Ph.D. rlhouse@email.unc.edu Associate Chair for Business Administration Laura Yurco 919-962-2173 laura_yurco@unc.edu Associate Director of Development Halie Sue Clifton 919-843-4454 haliesue.clifton@unc.edu Newsletter Editor, Designer, and Photographer Lars E. Sahl sahl@email.unc.edu At the Department of Chemistry, we feel strongly that diversity is crucial to our pursuit of academic excellence, and we are deeply committed to creating a diverse and inclusive community. We support UNC’s policy, which “affirms the University’s commitment to providing an inclusive and welcoming environment that is free from discrimination on the basis of age, color, creed, disability, gender, gender expression, gender identity, genetic information, national origin, race, religion, sex, sexual orientation or veteran status.” CONTACT US Department of Chemistry University of North Carolina at Chapel Hill Campus Box 3290 Chapel Hill, NC 27599-3290 chemistry@unc.edu 919-843-7100

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TABLE OF CONTENT From the Chair Letter to Alumni and Friends Bicentennial Information Awards and Honors David Nicewicz Awards and Honors Robert Parr - In Memoriam Changes at the Helm Nancy Ray Longevity Jillian Dempsey’s Banner Year Graduating Twins Translational Science CURE-ious Chemistry Congratulations John Thomas Why I Give to Chemistry SAY YES!!

FRONT COVER The Venable and Murray Halls courtyard. BACK COVER The Catalpa tree by Kenan Labs in spring bloom.

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From the Chair

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Jeffrey Johnson

A. Ronald Gallant Distinguished Professor; Department Chair

Dear Friends of Carolina Chemistry, On November 8th, I had the pleasure of presiding over our annual Department of Chemistry Junior-Senior banquet. This event is a wonderful opportunity for us to gather in the midst of a hectic time of the semester to recognize the accomplishments of our chemistry majors. We were honored to be joined by our former colleague and current Washington University Provost Holden Thorp. As we gathered, foremost on our collective departmental mind was the department’s Bicentennial Celebration, which will take place next year, culminating in our on-campus celebration on the weekend of April 20-21. Please mark your calendars and plan to join us! You will find a sign-up link inside this issue. In the context of our upcoming Bicentennial, I would like to begin my annual message to you with some of the reflections that I shared with our majors at the banquet: “You are majors in a program that has a long and storied history. For seniors, you will graduate in the year that marks the 200th birthday of the Department of Chemistry’s founding. In a world of the ephemeral, Instagram, and SnapChat, an institution with nearly 200 years under its belt merits some reflection. I will ask two semi-rhetorical questions: Why has Carolina Chemistry been here for 200 years and why should you care? Let me take a crack at the former question first. There is no right or wrong answer as to the durability of the Department, but I would submit that the longevity is intimately linked to the people – faculty, students, and staff - that have inhabited our buildings. Cutting edge modern research facilities are important, but the Department was excellent even when we labored in the decrepit Venable Hall, long after it had outlived its usefulness as a research building. Faculty hiring is treated as a process that merits the level of thought and surety of deciding to get married. We as faculty look very carefully for colleagues committed to student success, to excellence in the classroom, to world-class research; to those that embody the Carolina Way. Additionally, our staff show impressive longevity with the Department. Continued on page 15 CHEM.UNC.EDU | CHEMISTRY AT THE UNIVERSITY OF NORTH CAROLINA |

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Dear Colleagues, Fellow Alumni, and Friends, We are delighted to invite you to join us in celebration of the Chemistry Department’s, our Alma Mater’s, 200th anniversary. We hope that you will join your fellow graduates and proud alumni in the celebration of this very special moment, which is scheduled for a beautiful spring weekend on Friday, April 20 and Saturday, April 21 2018, in Chapel Hill. The founding year of 1818 marked the formal beginning of chemistry education and research at UNC. Two centuries later, we are delighted to report that there has never been a more exciting time to be a part of the UNC Chemistry Family. Through the collective efforts of faculty, staff, students and alumni, our department ranks 15th in the nation with worldclass accomplishments in research and education, positiveley, and materially, affecting the world we live in. We trust your time at UNC has shaped your professional and personal lives in significant ways, as it did ours. An ever-evolving vision, built on a steadfast foundation of research and education, has been a key component to the department’s success. Under the leadership of Dean Kevin Guskiewicz and Chair Jeffrey Johnson, UNC Chemistry has identified three strategic priorities to enable our vision to “create new knowledge in chemistry for the benefit of the world and its people.” Those priorities are to:

1. Implement a sustainable growth financial model that enables high-impact education and research in chemistry 2. Expand educational opportunities for graduate and undergraduate students 3. Diversify our faculty and student body Approaching our department’s 200th birthday, we are encouraging and welcoming you to become a part of this new chapter in Carolina Chemistry history. Please visit Chemistry’s giving page, where you will find a list of departmental priorities, and recommended levels for giving. We hope you will join us in philanthropic support of the department. Through our giving we enable research and education, which ensures the continuation of excellence we enjoyed at UNC Chemistry, and that it continues for future generations to come. We are delighted that you are a part of the UNC Chemistry family, and with utmost gratitude, we thank you for all you have done, and all you will do for our beloved department and University. Please do not hesitate to contact us with any questions. We look forward to seeing you in April, as we gather to reconnect with each other as fellow graduates and proud alumni and to celebrate the bicentennial “birthday” of our beloved department of Chemistry.

Yours Sincerely,

Tomas Navratil ’98, Ph.D. ’03 Chemistry Advisory Board Member

Chris Killian, Ph.D. ’96 Chemistry Advisory Board Member

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Chemistry Bicentennial Celebration Preliminary Program

Friday, April 20, 2018

Interspersed between Saturday’s listed events, will be several other activities such as divisional poster sessions, lab tours, “meet your professor” opportunities, social hour, and more speaker presentations. Please join us! Come back home to Chemistry and Chapel Hill in spring!!

3:00pm – 9:00pm Alumni Hall – Carolina Club Welcoming Remarks

Jeffrey S. Johnson

Chair, Department of Chemistry Welcoming Remarks

Carol Folt Chancellor

Alumni Social - Cocktails/Reception, followed by a banquet

Holden Thorp

Provost, Washington University in St. Louis Keynote Speaker

Saturday, April 21, 2018 Full Day Alumni Hall – Carolina Club Departmental Scientific Overview

Marcey Waters

Glen H. Elder, Jr. Distinguished Professor Departmental Fundraising Priorities

Lowry Caudill

Board Member, Carolina Research Ventures Research in the Dempsey Lab

Jillian Dempsey Assistant Professor Keynote Address

Joseph DeSimone

Chancellor’s Eminent Professor of Chemistry; Co-Founder and CEO of Carbon

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Samulski Honored with ACS Herman F. Mark Award Carolina Chemistry Professor Emeritus and former Chair of the Applied Sciences Department, Edward T. Samulski, has been awarded the Herman F. Mark Polymer Chemistry award for 2017. This award is one of the highest honors bestowed by the ACS Division of Polymer Chemistry and recognizes outstanding research and leadership in polymer science.

Samulski’s major advances include adapting nuclear magnetic resonance to map the stress in elastic networks, sheared polymer melts, “RheoNMR,” and the discovery of a biaxial nematic, a phase with implications for fabricating ultra-high strength polymers. He cofounded two startups, Allotropica Technologies, 2008, which makes “extreme materials for extreme conditions,” and Carbon, 2013, which pioneers a new 3D printing method based on oxygen-inhibited free radical polymerization. He served as a senior science advisor to the State Department from 2005 to 2006.

Hogan Receives Gates Foundation Scholarship Research Assistant Professor Brian Hogan, who is also the Director for Carolina Covenant and Achieve Scholars Program, was selected by the Bill and Melinda Gates Foundation to participate in the 8th Annual ASU GSV Summit, in Salt Lake City, Utah.

In 1989, through judicious hiring and the development of curricula integrated with traditional chemistry courses, Professor Samulski established UNC’s internationally recognized polymer chemistry program, while simultaneously maintaining his top research program, spanning a range of topics based on the interplay of basic polymer physics, and inherent molecular orientational order found in liquid crystals. This past year and a half, Professor Samulski returned from retirement to lead a Task Force, creating the Department of Applied Physical Sciences, Carolina’s first new science department in forty years. He subsequently served as the Department’s first Chair.

Through this highly competitive Scholarship Program, the Bill and Melinda Gates foundation are convening over one-hundred presidents, provosts, academic officers, and other institutional leaders to participate in the Summit alongside 3,500 other leaders from across the education ecosystem; all of whom care deeply about scaling innovation in education in order to improve outcomes for all students.


Pielak Alumnus Receives Hanna Gray Fellowship A former undergraduate research, and recent Master's student in the Pielak Group, Christopher Barnes, is one of 15 recipients of a 2017 Hanna Gray Fellowship from the Howard Hughes Medical Institute. Christopher, who was a chemistry major and played varsity football at UNC, was both an undergraduate and a graduate student in the Pielak Lab. There, he helped design a bioreactor for in-cell NMR, for which the group was awarded a patent, and the connected papers made the cover of the Journal of Magnetic Resonance. He also used in-cell NMR to make seminal contributions to our understanding the dynamics of protein in living cells. Each fellow will receive up to $1.4 million in funding over eight years, with mentoring and active involvement within the HHMI community. In this two-phase program, fellows will be supported from early postdoctoral training through several years of a tenure-track faculty position.

Gerardo Perez-Goncalvez Caltech WAVE Fellow We featured Gerardo Perez-Goncalvez in our previous newsletter, congratulating him on catching the attention of Caltech’s Professor Harry B. Gray, and subsequently become a member of the Pielak Group. Well, it is time to mention Gerardo’s continued success. We now congratulate Gerardo Perez-Goncalvez, wo continues as an undergraduate researcher in the Pielak Group, for having been accepted into Caltech’s WAVE Fellowsprogram. This program aims to foster diversity by increasing the participation of underrepresented students in science and engineering Ph.D. programs and making Caltech’s programs more visible and accessible to students not traditionally exposed to the institution. This Fellowship will be a fantastic way for Gerardo to increase his research experience, build his academic and professional network, and help him prepare for his continued academic path. The program will pay a weekly stipend of $600 for the ten week fellowship, and will also provide funds for travel.

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In Good Company! Professor David Nicewicz was selected as the 2017 winner of the prestigious Hirata Award by the University of Nagoya. The late Professor Yoshimasa Hirata with Nagoya University, was a giant of natural product chemistry in Japan. Many prominent Japanese professors are from the Hirata School, including Professors Koji Nakanishi, Yoshito Kishi, and Daisuke Uemura. In honor his prominence, the Yoshimasa Hirata Memorial Lectureship was established in 2004. The lectureship was awarded every year to a relatively young chemist who has made significant original contributions to the field of organic chemistry.

Through its splendid ten-year history, the Hirata Award has become significant in the field of organic chemistry. From 2015, the tradition of the memorial lectureship was renewed as “The Hirata Award� and it has been sponsored by Institute of Transformative Bio-Molecules, ITbM. Past winners are Professors Justin Du Bois, David Liu, Phil Baran, Peter Seeberger, Scott Miller, Jeffrey Bode, Jin-Quan Yu, Mohammad Movassaghi, Tobias Ritter, Martin Burke, Ashraf Brik, and Emily Balskus. Professor Nicewicz joins a distinguished fellowship, indeed. Congratulations, David!

Professor David Nicewicz, front left, in the very best of company - his research group.

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Waters AAAS Fellow

Professor, Marcey Waters, is being honored for her fundamental studies of molecular recognition in water and its role in biomolecular recognition, with application to epigenetic regulation, which encompasses the factors that control gene expression. Waters is the Glen H. Elder, Jr. Distinguished Professor of chemistry and vice chair for education, as well as the current president of the American Peptide Society. She was the principal investigator on a study, backed by a $1M grant from the W.M. Keck Foundation, of protein methylation, which is a mechanism of epigenetic regulation implicated in many diseases, including cancer. - Congratulations, Marcey!

Li NIH Awardee

Bo Li, an Assistant Professor has received a New Innovator Award from the National Institutes of Health, NIH. Li focuses her research on bioactive small molcules produced by bacteria and the ways in which they may help defend the human body against infectious diseases. Her lab is dedicated to unlocking the hidden chemistry of bacterial genomes and discovering the next generation of antibiotics, and the New Innovator Award will support research to identify novel combinations of antibiotics that exert synergistic activity against multidrug-resistant bacteria. Li is a previous winner of a Packard Fellowship and an NSF Career Award.

Achievement Award

Kenan Distinguished Professor of Chemistry, Biochemistry and Biophysics, Gary Pielak, has been awarded the prestigious 2017 University Mentor Award for Lifetime Achievement. The University Committee on Teaching Awards found abundant evidence of Dr. Pielak’s outstanding contributions to teaching. Both his students and faculty colleagues were enthusiastic in their praise of his continuing commitment to the highest standards of teaching and to education in general, and commended him for having provided a “rich, supportive environment for higher learning and an exceptionally positive role model which all of us honor with this award.” Professor Pielak, far left, and his research group.

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Robert Ghorm In Memoriam

One of the giants of theoretical chemistry, and a long-time member of our department, Professor Emeritus Robert Ghormley Parr, passed away on March 27, after a brief illness. Parr received an A. B. degree magna cum laude from Brown University in 1942, and then entered the University of Minnesota, receiving a Ph.D. in physical chemistry in 1947. He joined the faculty at Minnesota upon receiving his doctorate, and remained there one year. In 1948 he moved to the Carnegie Institute of Technology, now Carnegie Mellon University, in Pittsburgh, Pennsylvania, becoming a full professor in 1957. In 1962

“

Professor Parr was a pioneer the field of ab initio quantum chemistry since the 1950’s. His book entitled Quantum Theory of Molecular Electronic Structure, Benjamin 1963, was most influential at that time. Parr constructed the zero-differential overlap approximation and later, with Pariser and added by Pople, developed the influential Pariser-Parr-Pople, PPP, method. The PPP method was a landmark in the development of quantum chemistry and is still very widely used. In the early seventies, Parr had the vision to realize that density-functional theory, DFT, could very well turn out to be the method of choice for quantitative calculations on systems of chemical and biological interest, especially for those with large numbers of electrons. Parr had the foresight to begin his research in DFT long before it was as popular or as fashionable as it is today in the chemistry community. In fact, for years Parr was virtually the only chemist of his generation to pursue DFT. He had the courage to do this despite the fact that he was often criticized, and even ridiculed at times, for it.

R Parr wa rare sci and a s person made th contrib to chem

Parr led the research community in the construction of approximate functionals for practical applicaProfessor Parr and his daughter Jeanne Lemkau at his 92nd birthday celebratory symposium tions in chemistry. The Lee-YangParr correlation energy functional, also known as the LYP functional, he moved to Johns Hopkins University in Baltimore, Maryland, Phys. Rev. B 37, 785, 1988, has been cited more than 48,000 and in 1974 to the University of North Carolina at Chapel Hill, times. The LYP functional played a most critical role in bringing where he received appointment to an endowed professorship density functional theory to its practical application in chemisin 1990 and where he last taught. try, which ultimately led to the award of the 1998 Nobel Prize in

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mley Parr

Robert as a ientist special who hrilling butions mistry...

chemistry to Walter Kohn for his work on density functional theory and John Pople for his work on ab initio quantum chemistry.

Catalyst–Oxide Assemblies An important element in synthetic organic chemistry has been the development and application of organic excited states in solution, either by sensitization or electron transfer catalysis. Exploitation of organic excited states has evolved from the bench scale to the photochemical reactor scale.

Parr’s contributions to chemistry are characterized by his visionary approach and his foresight. In the speech at the American Chemical Society Southeast Regional Symposium in honor of Parr in 1998, Chemistry Nobel Prize winner John Pople summarized Parr’s contributions: “I have followed Bob Parr’s footsteps throughout my career, starting from the field of semiempirical quantum chemistry to the latest effort in density functional theory.”

In addition to his ground-breaking contributions to computational quantum theory, Parr was, of course, considered the father of conceptual DFT for chemistry, as clearly presented in the acclaimed Parr-Yang book, Density-Functional Theory of Atoms and Molecules, 1989.

Robert Parr was a rare scientist and a special person who made thrilling contributions to chemistry while profoundly affecting the lives of the many young scientists whom he mentored and who have had contact with him and his work. In honor of Bob Parr’s scientific achievements and on the occasion of his 92nd birthday, an international conference “Frontiers of Theoretical Chemistry - the Parr Celebration,” was held in the Auditorium of French Family Science Center at Duke University, on Saturday, September 7, 2013. Over fifty participants, Parr’s scientific and international family and friends, gathered to present exciting new progress in the field Parr pioneered. There were over twenty presentations throughout the day. The meeting ended in the evening with a symposium dinner, where there were more speeches on reminiscences about Bob’s life and career. Obituary originally published in Angewandte Chemie, and is used by permission.

In a parallel effort, with a different focus, advances have also been made in exploiting nanoparticle oxide surfaces for energy conversion applications based on chemically bound molecular reactants, which has the advantage of maximization of the local microscopic surface volume for enhancing efficiencies. In a collaborative effort between the David Nicewicz and Thomas Meyer groups, published in PNAS, researchers describe the integration of the two areas with the goal of creating stable photochemical environments that minimize reaction volumes in photooxidation reactions. The results presented, provide a basis for extension to larger scales and to catalyst–oxide assemblies with potential applications for larger-scale organic reactions.


Ruth Retires

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fter fourteen years of dedicated service to the Department, and thirty years of service at the University, our Business Manager, Ruth Hyde, retired on November 17th. During her time with us, she managed one of the most complex units in the University. Ruth was always the calm epicenter in all of our activities, and handled her heavy workload with courtesy and professionalism, never failing to recognize and convey that our human resources are the most important assets in our unit. Ruth served the department with distinction and was a valued member of the leadership team for seven, yes seven, Department Chairs, which has to be a record. She directed the administrative operations of the department with a high level of skill and efficiency, implementing many improvements that will have long-time positive impact on Chemistry operations.

“The stability in the departmental administration and staff is especially noteworthy and is a great testament to the environment Ruth helped foster,” says current Chair, Professor Jeff Johnson. He continues, “she was a tireless advocate for staff behind the scenes; all of us in the Chair’s position have appreciated her counsel, and we will miss her expertise in navigating many byzantine University policies.”

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Laura Begins

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e wish a warm welcome to Laura Yurco, MBA, as the Department’s new Associate Chair for Business Administration. Laura is an accomplished business professional with over thirteen years of University and academic accounting experience. She comes to the Department from the College of Arts & Sciences, where she was the Senior Director of Budget Management. She has also held various accounting and management roles within central offices and departments, including Budget Analyst in the College, Accounting Manager for the Department of Psychology, the Department of Otolaryngology, and as an Accounting Technician in the School of Public Health Dean’s Office.

Laura has formed many strong relationships with Managers, Faculty, and Central Campus constituents from her time in the College and within departments; her experience and skills will be very beneficial for our Department. She has also managed a wide range of fund types including state, facilities and administration, contract and grants, clinical, discretionary trusts, endowments, and expendable funds. Laura also brings experience in the management of contracts and grants from pre to post-award, for a variety of federal and private agencies. Laura is a highly motivated and successful individual, and we look forward to working with her as we build on past successes and continue to implement the Department’s strategic plan.

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Nancy Ray - Thirty Years of Service! This is how happy Nancy Ray looked on the day she celebrated thirty years of service with the University! She was celebrated, congratulated, and lauded by staff, students, and faculty, who are all in awe of her ever-smiling attitude, deep knowledge of everything HR, and can-do attidtude. Our department is lucky to have her! Nancy started with the University in April of 1987, working in the UNC Division of Plastic and Reconstructive Surgery and Surgery of the Hand, as a medical secretary. She remained there in a couple of different positions until she joined Chemistry, in August of 1998. Her first task here was as Student Payroll Coordinator. She moved into her current postion as Human Resource Manager in November of 2001. Thank you for all you do, Nancy!

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Jillian Dempsey A BANNER YEAR!

Sitterson Teaching Award

Professor Jillian Dempsey, who began her career at UNC in 2012 and over the past five years has developed a vibrant research program in physical inorganic chemistry, which has been supported by the NSF CAREER Program, Alfred P. Sloan Fellowship, a Packard Fellowship for Science and Engineering, the Department of Energy and an Air Force Office of Scientific Research Young Investigator Award, has indeed had a very

nate deserving faculty and graduate teaching assistants for the awards and subsequently oversee the selection process. The committee chose recipients who promote the value of undergraduate teaching by example, demonstrate concern for students through interaction and approachability inside and outside the classroom, create meaningful learning experiences and maintain high expectations of their students. “Rewarding student-teacher relationships are the foundation for success at our University,” said James W. Dean, Jr., Executive Vice Chancellor and Provost, at the award ceremony. “Carolina is always proud of its talented faculty, and it is especially satisfying when students help the University recognize the meaningful impact our teachers make to their lives.”

Chemical Education

Later in the year, Jillian published an article discussing the necessity of technical writing in Chemistry. In it, she elaborates on the need for writing skills, which often first becomes pronounced during a chemist’s graduate studies. Beyond writing of manuscripts and a thesis, many graduate programs require students to write original research proposals in order to cultivate skills associated with proposing new ideas. This requirement is particularly helpful for those students who go on to be academic faculty because writing grants and proposing new research is a crucial part of running a laboratory.

accomplished year. It began by her being awarded the 2017 J. Carlyle Sitterson Award for Teaching First-Year Students. Sitterson awardees are selected by the University Committee on Teaching Awards, based on input from students, who nomi-

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In the article, Jillian points to the plethora of writing requirements and expectations for graduate students, which continues into their professional careers, particularly for academic chemists, and raise an important question: when do students learn the necessary skills, particularly good grant-writing skills? A number of undergraduate-level writing courses or inclass exercises have been proposed. However, states Jillian, it is unclear what percentage of students have exposure to these classes.

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Jillian’s work, written with former graduate student, Brian McCarthy, was published in the Journal of Chemical Education and introduce a graduate-level course, now featured in the Carolina Chemistry curriculum, focused on writing original research proposals to address the uneven preparation in technical writing of new chemistry graduate students. The general course structure features extensive group discussions, small-group activities, and regular in-class small-group peer review. Since the introduction of this course, it has been found by student surveys, faculty feedback, and student success in winning graduate fellowships, that the course is a valuable graduate

Graduate Fellows will be provided with structured mentoring, professional development opportunities, and travel funds to attend conferences to present their research and network. “The attrition of women in chemistry pursuing academic careers is startling, and research has shown that lack of both mentoring and female role models are major factors influencing women’s departure from the tenure track,” says Jillian. “At UNC, we have done a great job recruiting women to our graduate program in chemistry and supporting them as they pursue their degrees. With help from the Clare Boothe Luce Program, we will be able to pilot enhanced mentoring and professional

Professor Jillian Dempsey in the midst of her research group

education component. The work details course structure, pedagogical approach, and course evaluation.

development opportunities designed to narrow the gap between degrees awarded and women in tenure-track academic positions.”

STEM Grant

Family Addition

Later in the year, Jillian Dempsey was named the principal investigator for a $300,000 grant from the Clare Boothe Luce Program. This grant will support three new graduate fellowships for women in Chemistry who are aspiring to tenure-track academic positions at UNC-Chapel Hill. Concurrently, the University has committed to an additional fourth fellowship. The

And as if the year was not busy enough, Jillian and her husband also welcomed their first child, a baby boy named Orin, on April 12th. Orin has already made appearances at regional and national American Chemical Society meetings, and has a set of periodic table blocks to help him master chemistry basics.

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Joshua and Isaiah Gober - Twin Ph.D.’s Department faculty members were excited to have twin brothers Joshua, on the left in the above image, and Isaiah, to the right, Gober join us as graduate students. They have graduated together since kindergarten, always receiving highest honors and adulations, so we had high hopes that they would bring that same energy and enthusiasm to their work here. We were not disappointed, as both of them successfully defended the doctoral theses earlier this year.

only author other than myself,” she continues. Not only that, “this and a second project of his resulted in two patent applications, and subsequently to an NIH SBIR grant with a local company, Epicypher,” she concludes proudly.

Both Isaiah and his twin brother, Joshua, “arrived at UNC with with an impressive resume and a passion for chemistry,” says Professor Marcey Waters. She was thrilled when Isaiah chose to join her group. “His goal was to advance our fundamental work on molecular receptors for methylated lysine, a post-translational modification implicated in a number of diseases, into useful tools for sensing these modifications,” she says.

“Joshua was one of the first students to join my group, says Professor Eric Brustad, “and he proved to be a vital member of our team,” he continues. “Joshua was highly creative and independent, and though soft spoken, when Joshua talked science, everyone listened,” comments Brustad.

“Due to both his creativity and tenaciousness, Isaiah successfully accomplished his goal in my group, through a system of his own design,” comments Professor Waters. “Not only did he develop the sensor, he did the biological studies to demonstrate its utility,” she says. “And his work lead to an impressive first-author paper in JACS, with Isaiah as the

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Isaiah graduated this summer and took a job with CEM, a leading company in application of microwave technology to peptide and pharmaceutical chemistry based in Matthews, NC.

Joshua established an impressive program in the Brustad lab, developing cytochrome P450 based enzymes that carry out a non-natural carbene-mediated cyclopropanation reaction. Excitingly, he showed that many enzymes are capable of carrying out this reaction and that different protein scaffolds provide routes for different diastereomeric products. In addition, he developed a general strategy Continued on page 22

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From the Chair Continued from page 3

Our alumni also care very deeply about the Department. Earlier in November, we hosted the visit of our External Advisory Board, a group of alumni, leaders in their respective fields, who give freely of their own time to assist the Department in the issues it is facing. If the alumni are our past, you, our students, are the future and tomorrow’s leaders in multiple human endeavors. You are getting a truly unique foundation for what life holds ahead of you by investing your efforts in a Carolina Chemistry education. Why should you care about the Carolina Chemistry bicentennial? The same traits that have led to the Department’s longevity, allow you to study in a department where internationally recognized leaders in research and entrepreneurship are also worldclass classroom instructors, bringing innovative new instructional techniques that transcend “rock on rock” methodologies of just a generation ago. Some things that are 200 years old are old and musty. I will make the argument that our Department’s longevity is a result of constant renewal. The faculty we hire are always seeking the new; working to find small molecules therapeutics to target RNA, to develop nanoparticles that release therapeutic NO, to revolutionize 3D printing by deploying novel chemistries. These three examples happen to have evolved to the point where each is a freestanding startup company having raised millions of dollars.

Arguably the most important piece of the renewal process in a university is its student body. You bring fresh ideas and fresh perspectives in ways that never cease to drive the research and teaching enterprise. We are grateful for the energy brought to bear on key scientific questions of the day and recognize you for those efforts tonight.” With this backdrop, I am happy to, in this issue of our Newsletter, share some recognitions and items of interest from the previous twelve months that I hope you find as exciting as I do. Please take this collection as representative rather than comprehensive! I will close as I began, with an invitation to join us here in Chapel Hill on the weekend of April 20-21 to recognize two hundred years of Carolina Chemistry. It promises to be a wonderful celebration of where we have been and where we are going. Please mark your calendars and plan to attend if at all possible! With my best wishes,

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Ribometr Translational Medicine

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or roughly a decade, Professor Kevin Weeks and his laboratory colleagues have been developing chemical technologies for interrogating the structures of RNA molecules and then using these technologies to understand new features of biology. RNA is that funny little molecule that lies between DNA and proteins according to first-year biology textbooks. It turns out that RNA functions in a much more complex way than that simple picture and, in fact, drives central communication links in all cells. The technologies developed in the Weeks lab are now collectively called SHAPE and RING chemistries, have been adopted by laboratories worldwide, and are featured in several recent textbooks.

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eeks lab members have used SHAPE and RING technologies to understand the structures of HIV

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and HCV genomes and to define mechanisms that underlie Huntington’s disease, leading to the proposal that RNA structure comprises another level of the genetic code. “This was all well and exciting” says Weeks, “but it became clear to us that we could use this same technology to potentially discover drugs to treat serious human diseases.” It turns out that a much larger fraction of the human genome is used to make RNA than to make proteins, but only a handful of current drugs actually target RNA. The bottom line was that RNA-targeted drugs represented a huge, exciting, and risky opportunity.

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r. Weeks started Ribometrix to realize this goal and recruited a former student, Katie Warner, to co-found the company with him. The key insight that inspires Ribometrix is that SHAPE and RING strategies can be used to

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RNA Image by Christine Hajdin


rix

Based on UNC Chemistry identify RNA motifs in therapeutically compelling RNAs that have cave-like clefts and crevices. Small molecules that bind in these clefts may modulate RNA function and the underlying biology. If successful, Ribometrix could make finding drugs that target RNA straightforward in the sense that targeting RNA will be no harder than targeting proteins, the cellular targets of most drugs. Weeks notes, “targeting proteins is still a big challenge, of course, but Ribometrix technologies are easily adapted to high-throughput screening of many RNAs and small molecules, so there is also a tremendous opportunity here.”

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rug discovery is expensive and so Weeks and Warner spent roughly two years working to convince funding agencies and outside investors that they had a special angle on drug discovery, especially on potentially high-reward but high-risk drugs that target RNA. Ribometrix has since received multiple grants from the National Institutes of Health and, critically, private equity funding, together totaling roughly nine million dollars. “Although Katie and I keep getting congratulated on all

this fund raising, I do not really see this as success at all,” emphasizes Weeks. “Drug discovery is an incredibly difficult and no-nonsense endeavor, which suits our personalities. We will not consider this completely successful until we have created new chemical matter that makes people’s lives better.”

R

ibometrix has moved to lab space in a renovated former tobacco-processing factory in Durham and has recruited leadership and scientific teams.The group is focusing on Huntington’s disease and on several targets that were previously thought to be “undrugable” but probably can be drugged with the novel RNA technologies that underlie the Ribometrix approach to drug discovery. “We now have a good shot at proving our ideas,” concludes Weeks. “Ultimately, if you want to make the largest possible impact with your university-created technology and ideas, a commercial company is often the best and most direct way to impact human lives. Lots of challenges ahead, but we are giving this our most aggressive efforts.”

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CURE-ious Che Purslane Chemistry

Madeline Cooke squats in the dirt and leans over the stacked, wooden two-by-fours supporting a raised garden. Scissors at the ready, she trims away weeds and checks the health of rows of red-stemmed succulents. Although many might consider this jade-like plant called Purslane a weed, it is actually edible, often found in Asian soups, salads, and stews. And is packed with antioxidants.

also wanted to get some type of chemistry research going in an undergrad lab course so students would have some purpose in their experiment other than making crystals to throw in the waste jar as they walk out.”

Nita Eskew, Ph.D., Director of Undergraduate Laboratories Course-Based Undergraduate Research Experiences, CURE, are part of the university’s Quality Enhancement Plan, a fiveyear initiative that is part of the 2017 Southern Association of Colleges and Schools Commission on College accreditation process. Cooke, a UNC senior majoring in chemistry, spent six months last year helping organic chemist and Director for Chemistry’s Undergraduate Laboratories, Dr. Nita Eskew, tend to these weedy plants so she could use them in her “Chemistry of Purslane” class. A Course-Based Undergraduate Research Experience, the class provides many students with their first active research experience. “Some students do not have the opportunity to do undergraduate research while they are here, so this gives them the experience while also getting course credit,” Eskew explains. “I

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Organic chemistry can be a little obscure, admits Eskew, so a course that highlights real-world applications draws more student attention. “It is helpful to have something more concrete you can put your hands on,” she says, adding that the class had so many applicants she were unable to accept them all. Purslane’s antioxidant content suggests it has medicinal properties, but it is largely understudied in the United States. Eskew hopes that she and her students can answer some basic questions about it. What are the main differences between the gold and red varieties? Does one have a higher antioxidant concentration than the other? Does the growing environment impact their chemical composition?

Encouraging Curiosity

Throughout the class, which first began in Spring 2017, Eskew teaches standard chemistry techniques like extraction and ul-

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emistry traviolet-visible spectroscopy for identifying antioxidants in plants. Although every student learns how to perform these procedures, Eskew encourages each individual group to cultivate their own sets of questions and experiments. “This is very much about not having a recipe,” Eskew points out. “It is about developing questions and going through the process of testing and modifying. And it is also about iteration.”

Portulaca oleracea, common Purslane

In a traditional chemistry lab, students will complete one experiment and then move onto a different one in the following lab. But in this class, they will continue to run the same experiments three times or more, tweaking them each week. “In research, you do not just do an experiment one time; you do it multiple times to try to improve it and see if you can reproduce results.” To test the Purslane for antioxidants, students perform a procedure involving a color shift that indicates when antioxidants are present. “Students can actually visualize what’s happening when the electrons are moving because they see a physical change in color,” Eskew says. “It makes the chemistry of it all more real.” “The first time my team completed the test we were really excited, because the procedure worked,” Cooke explains. “It felt very gratifying and made us all very enthusiastic.”

Growing Together

Before she developed the class, Eskew had never heard of Purslane. Not until Claire Lorch pointed it out on a tour of the Carolina Campus Community Garden, CCCG, a program of the North Carolina Botanical Garden located on Wilson Street that donates all its produce to university housekeepers. Lorch, the CCCG program manager, solicits volunteers from across campus and the greater community to work in the garden yearround. “I learned of Purslane when my dear friend Vimala, of Vimala’s Curry Blossom Cafe, pointed out the plant and its nutritional value,” Lorch explains. “From then on we stopped weeding it

and started planting it. Forty percent of the housekeepers are refugees from Burma and appreciate that we have Purslane in the garden.” Eskew’s partnership with the CCCG for the class means that it is also one of the Carolina Center for Public Service’s APPLES courses, which connect academic learning with community service. Students enrolled in the course, held once a week, must spend a minimum of thirty hours volunteering in the garden, some of which is used for lab time.

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Joshua and Isaiah Gober - Twin Ph.D.’s Continued from page 16

to improve the activity of these proteins via the introduction of simple and conserved mutations that led to robust and predictable outcomes. As a result of his efforts, Joshua is a co-author on five papers in journals such as JACS, ACS Chemical Biology, and ChemBioChem, from his time at UNC, including four first author papers! Joshua is now a senior research scientist at Genentech, one of the leading biotechnology companies and a pioneer in the development of protein-based therapeutics. Congratulations to both Jushua and Isaiah on your continued excellence! We wish you all the best and hope to see you back on campus for the Bicentennial Celebrations in April!

Congratulations, John Thomas! Our warmest congratulations to undergraduate chemistry major John Thomas, who has been selected to receive a scholarship from the Air Force Health Professional Scholarship Program, HPSP. John started at UNC studying chemistry as an Air Force ROTC student, and during his time in this program he grew to love the search and rescue mission field. He decided early to pursue a career as a physician in search and rescue, as he was inspired by the opportunity to provide emergency care to people all over the world. He knew that the Air Force offered opportunities for medical school funding, and that in order to qualify, he had to perform excellently both as a student, and cadet in the ROTC. So, John focused, and worked hard. Pre-med cadets compete for the HPSP scholarships at the beginning of their senior year, and John was one of the lucky few who learned that his hard work had been rewarded. He was one of only twelve Air Force ROTC cadets in the country to be granted an HPSP scholarship. The scholarship provides financial support to pay for all expenses, supplies, books, and full tuition required to whatever medical school John decides tor attend. Additionally, the scholarship provides a stipend to pay for living expenses. Upon completion of his medical degree, John will serve in the Air Force Medical Corps as a physician. -Congratulations to your dedication and recognition, John, and all the best wishes for your future!


CURE-ious Chemistry

Selective Transformations

Continued from page 21 Since completing the class last spring, Cooke, now Eskew’s teaching assistant, continues to dedicate her time to the garden each Sunday. “It is a unique experience in that it is inter-generational,” she says. “On campus, I do not get the opportunity to interact with people who are in different stages of their life, but community members and grad students come to the garden. Gardening is a lot of work with your hands so there is plenty of time to chat.”

The selective, and controllable, modification of complex molecules with disparate functional groups, for example, natural products, is a long-standing challenge that has been addressed using catalysts tuned to perform singular transformations, for example, C–H hydroxylation. In research published in Nature Chemistry, and also highlighted in ChemistryWorld, researchers in the Gagné Group demonstrate silylium ions combined with reducing counterions to forge chemoselective transformations on complex bioactive compounds.

Inspiring Others

During her own undergraduate career at Carolina, Eskew, a first-generation college student, never knew about research opportunities until her adviser suggested she pursue it one summer. She did not have any family or friends who were chemists, nor did she understand what chemists did outside the academic environment. This meant graduate school was not originally in the cards for her either, Eskew admits, but that same adviser encouraged her to apply. “By the end of that summer doing research, I was hooked with discovery and learning something new, and realizing that other people had never made the compounds I did or seen their reactions,” she says. “That is why I think this class is a great opportunity to give students a small introduction into what research is, especially for those who are first-generation or have never been exposed to research.” “Dr. Eskew is a really special person here at Carolina,” Cooke adds. “It is admirable that she put so much time into creating this class, and how dedicated she is to her students. I think getting research experience is one of the most important things during your undergraduate career. It has changed the way I think. To be put in a setting where no one in the room really knows the answer, and it is okay to not know the answer, that is great.”

Fluoroarylborane catalysts can heterolytically split Si–H bonds to yield an oxophilic silylium, R3Si+, equivalent along with a reducing, H–, equivalent. Together, these reactive intermediates enable the reduction of multiple functional groups. Exogenous phosphine Lewis bases further modify the catalyst speciation and attenuate aggressive silylium ions for the selective modification of complex natural products. Manipulation of the catalyst, silane reagent and the reaction conditions provides experimental control over which site is modified, and how. The ability to carry out varied and selective transformations under catalyst control across diverse natural product structures suggests that it will emerge as a powerful tool for the synthesis of new chemical entities that encircle the structure of natural products and drug candidates. Whether these structures have resulted from traditional medicinal chemistry, screening of natural product, fully synthetic libraries or diversity-oriented synthesis, the chemistry described in this publication will enable those hits to be diversified further, even if the substrates are already complex.

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Why I Give to Chemistry I recall my arrival at Carolina as if it were only a few years ago, rather than decades. An initial fascination with math and physics faded a bit as I learned that my mind worked differently than the minds of those destined for those fields. My first general chemistry course was intriguing but did not inspire. But courses in analytical chemistry with Tom Meyer, and organic chemistry with Robert McKee, sold me on the subject. Guidance and inspiration, in courses and in the lab, from Slayton Evans, Tom Baer, Ernest Eliel, and many others led to a desire to understand the workings of things.

Slayton in particular taught me that hard work and depth of understanding were more important than being smart. Slayton was also an avid fisherman and we used to wade the Eno River, fishing from bridge to bridge. So he provided education, inspiration, and recreation. Out of gratitude for his influence I have been pleased to contribute to the lectureship in his honor. The Chemistry Department was uniquely collegial. I remember nights in the lab or at the NMR machine, very primitive by today’s standards, seeing professors wandering through the labs during the night, going to bluegrass night at a local bar with the chemistry graduate students and many of the faculty, enjoying a community that was very supportive. With excellent teachers and with the opportunities provided by the Morehead Foundation, I was privileged to have a truly liberal education in the old sense of the phrase. Courses in history, music and literature, concerts and plays, and visiting artists enhanced the quality of life and caused me to explore how the various disciplines and arts fit together. These experiences enrich life even today. I was prepared for graduate school in Chemistry, but for reasons that are still a bit mysterious I ended up in medical school. The training at Carolina was good preparation for 20 years in academic hematology and oncology, and subsequently 20 years in clinical trials and clinical care. Though I’ve strayed from Chemistry, it all started in the Department. For several decades I have donated specifically to Chemistry. I am now honored, although probably unqualified to be on the Chemistry Advisory Board. I give to Carolina to honor excellent teachers and role models. I give to help support an institution facing public funding hurdles and adverse political winds. I also give because the future of our country depends on educated, resourceful, and creative young people. As we are about to celebrate the Bicentennial of Chemistry at Carolina we need to build on the past: “What’s past is prologue, what to come. in yours and my discharge.”

Spence McCachren, MD


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T R O P Y P R T U S S EMI H C

The “Say Yes” fund in Chemistry allows the Department Chair to say “YES” to special and often urgent requests from faculty and students for small amounts of support, which contribute greatly to their research and education. Even your smallest gift will make a tremendous difference in the Chair’s ability to support our outstanding faculty and students. Please follow the link below to help our Chair say “YES!” Your continued support is greatly appreciated. Thank you!

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CHEMISTRY

Profile for uncchemistry

Fall 2017