Science of Synthesis Update on Purines

Recent developments in purine synthesis have been reviewed by Prof. Stanislav Wnuk and colleagues.

A team of researchers from Florida International University (Miami), led by Prof. Stanislav Wnuk, have recently compiled a review of significant developments in the synthesis of purine-containing compounds for Science of Synthesis. This timely contribution brings together the most significant developments reported in recent years for the synthesis of purine-containing compounds, which have been widely investigated for the development of antiviral, antiretroviral, antibiotic, anti-inflammatory, and anticancer agents. To access the chapter on Science of Synthesis, click here.

The 164-page team-effort, by Prof. Wnuk, Dr. Yong Liang, Dr. Zhiwei Wen, Dr. Maria de Cabrera, and Md Abu Hasan Howlader, includes approaches for constructing the purine core itself (e.g., via ring-closure reactions) and also methods for modifying purine-containing compounds. There is a particular emphasis on the regioselective C-H functionalization of purines, as well as transition-metal-catalyzed cross-coupling reactions of halopurines. Recent methods for the preparation of azidopurines, which have found useful application in click reactions for biological probes and imaging agents, are also discussed.

The Volume Editor for this contribution was Dr. Jie Jack Li, currently Vice President of Discovery Chemistry at Shanghai ChemPartner. Dr. Li comments: “Purine and purine analogues are of paramount importance in drug discovery. Many purine analogues are antimetabolites that mimic the structure of metabolic purines. The most prominent drugs include thiopurines, azathioprine, and mercaptopurine. Prof. Wnuk and colleagues have done a great job in updating the advances of chemistry of purine and analogues. It will serve as an invaluable resource for the community working on purine and purine analogues.”

This an update to the original (2003) Science of Synthesis review on purines (by Prof. Frank Seela, Dr. Natalya Ramzaeva, and Prof. Helmut Rosemeyer).

 

Dr. Yong Liang — SOS Author for Chapter 16.17Dr. Yong Liang was born and grew up in Beijing. He received his bachelor’s and master’s degree in chemistry from Shaanxi Normal University in China. During the last year of his master's study, he came to Florida International University as a visiting scholar, and then became a full-time doctoral student, receiving his Ph.D. degree in 2014 under the guidance of Dr. Stanislaw Wnuk in nucleoside chemistry. After graduation, he joined the Beckman Research Institute as a staff scientist. He is currently working on the chemical synthesis and modification of nucleosides and oligonucleotides.

Dr. Zhiwei Wen received his Ph.D degree in Chemistry from Florida International University in 2018. His dissertation research in Dr. Stanislaw Wnuk’s lab was focused on organic chemistry of nucleoside/tide analogues with applications in biochemistry and in anticancer, antiviral, and antibacterial medicine. He has been a postdoc in Dr. Kenneth Jacobson’s lab at the National Institutes of Health since 2018. His is currently working on the synthesis of subtype-selective agonists and antagonists for GPCRs as well as characterization of their pharmacological properties.

Dr. Maria de Cabrera graduated with her PhD in Chemistry from Florida International University (FIU) in July 2019. At FIU, she worked under the supervision of Dr. Stanislaw Wnuk on the synthesis of nucleoside analogues for Positron Emission Tomography Imaging and on the chemistry of azido nucleosides to study radiation-mediated generation of aminyl radicals from azides. Since her graduation, she has focused on chemistry education, working as a teacher and professor.

Md Abu Hasan Howlader is a PhD candidate in the Department of Chemistry and Biochemistry at Florida International University (FIU). His primary research focuses on the synthesis of nucleoside/tide analogues with purine bases modified with reactive probes at the C2 or C8 position. He is also developing the chemical synthesis of organoarsenical antibiotic arsinothricin (AST) and its derivatives. Furthermore, his research interests involve the synthesis of polyaromatic hydrocarbons (PAHs) to study the growth mechanisms of polycyclic aromatic hydrocarbons. He is expected to graduate with his Ph.D in the summer of 2021.

Professor Stanislav Wnuk — SOS Author for Chapter 16.17Prof. Dr. Stanislaw F. Wnuk received his Ph.D. in 1983 and his habilitation in 1995 from Adam Mickiewicz University in Poznan, Poland. He undertook a postdoctoral fellowship with Professor Morris Robins at University of Alberta, and then continued to work with Robins at Brigham Young University. In 1997, he joined Florida International University in Miami, where he later served as Chair of the Chemistry and Biochemistry Department and Associate Dean for Graduate Educations. His research interests involve organic chemistry of carbohydrates and nucleosides with applications in biochemistry and in anticancer and antiviral medicine. Another area of his research focuses on fluorinations and cross-coupling methodologies. He is an author of over 150 research articles, 10 book chapters, and 5 patents. Click here to visit Prof. Wnuk’s research group page.

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