Carbohydrate chemistry/glycoscience

The inspiration for this issue on carbohydrate chemistry arose from the Kyoichi A. Watanabe Commemorative issue organized by Steve Patterson, Guest Editor. The touching editorial [1] not only outlined Watanabe’s amazing academic achievements, including synthesis of therapeutic nucleosides and carbohydrate transformations, but also provided insights into his broad influence (impact) and his wonderful character. The contributed papers covered a specific range of carbohydrate topics including a review of nucleoside inhibitors of inosine monophosphate dehydrogenase [2], synthesis of an AZT analogue [3], and the synthesis of various therapeutic nucleosides [4], [5], [6], [7], [8], [9], [10].

Carbohydrate chemistry is an expanding area in chemistry and biochemistry. The importance of glycoscience/carbohydrate chemistry is clearly outlined in the National Research Council report: Transforming glycoscience: A roadmap for the future – NCB1 [https://www.ncbi.nlm.nih.gov/pubmed/23270009], the NIH funding opportunities [https://commonfund.nih.gov/glycoscience/fundingopportunities#current] and the increasing number of publications [https://www.ncbi.nlm,nim.nih.gov/pubmed/?Term=glycol*] in the field. An effort has been made to include additional areas of carbohydrate chemistry as well as those that are more traditional. The issue begins with an excellent review of boron-based compounds as potential therapeutics and for detection applications by Binghe Wang (Associate Dean/Regent’s Professor/Eminent Scholar in Drug Discovery/Georgia Cancer Coalition Distinguished Scholar at Georgia State University). Wang is the Chief Editor of Medicinal Research Reviews, a high impact journal and the founding editor of the ‘Wiley Series in Drug Discovery’. He has trained a large number of scientists at various levels and published over 200 papers. Several of his boronic acid-diol complexation papers are among the most cited in the sugar recognition field [11], [12], [13].

Markus Germann has provided an extensive review on the effect of modifying ribose sugars on nucleic acid structure and function. Markus Germann obtained his PhD in nucleic acid biochemistry under the direction of Van de Sande; did postdoctoral work on nuclear magnetic resonance (NMR) structural determination with Vogel and was an NMR application specialist with Bruker-Spectrospin. He joined Thomas Jefferson University in Philadelphia as an Assistant Professor. Upon promotion, he moved to Georgia State University’s Department of Chemistry as a Georgia Cancer Coalition Distinguished Scientist. His interests include DNA damage/repair, macromolecular structures and design of antiviral agents. His current research deals with the effect of modified nucleotides on DNA structure [14].

Todd Houston has contributed a communication related to boronic acid structure. Houston moved to Griffith University in Australia form Virginia Commonwealth University in 2001. He is currently a Research Leader at the Institute of Glycomics. He studies recognition of cell-surface carbohydrates and applications of glycosides inhibitors and aminoglycosides against disease. He has reported a fluorescent boronate receptor with a response specific for free sialic acid [15].

A contribution by Anatoly Yatsimirsky provides the latest information on sugar recognition by bis-boronic acid containing derivatives. Anatoly Yatsimirsky obtained the rank of Professor at Moscow State University. Subsequently, he moved to the National Autonomous University of Mexico as a Professor. His interests include physical organic chemistry, molecular recognition and catalysis. He has over 190 publications including a monograph on supramolecular chemistry. A recent publication [16] addressed important concerns regarding boronic acid-polyol complexation questions raised in Binghe Wang’s seminal early work [12]. An analysis of pH profiles of binding constants and a description of electronic effects on boronic acid complexation (Hammett and Brønsted correlations) are presented. Another paper [17] extends applications of boronic acids to anion recognition.

Suri Iyer’s contribution focuses on the recent work on detection of influenza viruses. Suri Iyer received his PhD on the development of chiral metal alkoxides for ring opening polymerization. Subsequently, he synthesized complex glycans (potential anticoagulants) at Emory University and then moved to the Biosensor Group at Los Alamos to synthesize glycans for biosensing applications. He started his academic career at the University of Cincinnati. After tenure and promotion, he moved to the Center for Diagnostics and Therapeutics at Georgia State University. His group works in the interdisciplinary area of glycoscience developing probes to understand how infectious agents interact with cell surface carbohydrates to gain entry into cells. A recent paper describes an innovative way to detect the virus using a glucose meter [18].

Peng Wang and Jun Zhou present a potential general protocol for the glycosylation of nitrogen containing molecules. Peng Wang obtained his PhD from UC Berkeley, carried out postdoctoral work at Scripps and joined the faculty at the University of Miami. Subsequently, he moved to Wayne State University and then to Ohio State University as Ohio Eminent Scholar. He joined Georgia State University as a Georgia Research Alliance Eminent Scholar in Chemical Glycobiology and is the current Chair of Chemistry. He has published over 400 research papers as well as a substantial number of reviews, book chapters and patents. His research interests have focused on the field of carbohydrate chemistry and glycobiology for the past 23 years. Jun Zhou is a postdoctoral fellow in Wang’s group. He is focused on the development of chemical glycosylation and chemo-enzymatic synthesis of N-linked glycans and glycopeptides. After obtaining his PhD under the direction of Wenbao Hu, he trained in medicinal chemistry at GlaxoSmithKline North Carolina (Research Triangle). A recent publication [19] deals with oligomannoside synthesis.

Ibrahim Abdou has contributed an article on the synthesis and antimicrobial activity of 4-trifluoromethylpyridine nucleosides. Ibrahim Abdou received his PhD at Georgia State University, did a postdoctoral fellowship at Georgia Institute of Technology and took an academic position in Chemistry at UAE University where he has been promoted. His research interests are the design of nucleosides and nucleotides as anti-cancer agents, charge transfer in DNA, drug-DNA interactions and solvent-free microwave-assisted synthesis. A paper on the synthesis and activity of pyrimidine glycosides [5] has recently appeared.

Rajendra Srivastava has presented the synthesis of 2,3-unsaturated O-glycosides using conventional and microwave methods. Rajendra Srivastava obtained his PhD in India and ran the Laboratory of Organic Synthesis in the Centro de Ciencias Exatas e da Natureza at the Universidade Federal de Pernambuco, Brazil, until his retirement. His research interests include the synthesis of monosaccharides and synthesis of heterocycles. A recent paper deals with the synthesis of selected 2,3-unsaturated O-glycosides [20].

Yasutaka Shimotori’s article focuses on the synthesis of glycosyl hydroxybenzoates. His research interests center on the synthesis of optically active compounds using lipase as a catalyst. He is an Associate Professor at the Kitami Institute of Technology in the School of Regional Innovation and Social Design Engineering: Biotechnology and Environmental Chemistry. A recent paper presents the synthesis of triazole derivatives [21] using cross-coupling click chemistry.

Naoufel Ben Hamadi’s contribution deals with the synthesis of carbohydrate-derived isoxazole derivatives. He is affiliated with the Laboratory of Synthesis, Heterocyclic and Natural Products in the Department of Chemistry at the University of Monastir, Tunisia, and with the Department of Chemistry, College of Sciences at Al Imam Mohammad Ibn Saud Islamic University, Riyadh, Saudi Arabia. His research interest focuses on supramolecular chemistry and catalysis.

Wei-Wei Liu’s article describes the synthesis and bioactivity of glycosyl triazole derivatives. Wei-Wei Liu is a member of the College of Pharmaceutic Sciences and the Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening at Huaihai Institute of Technology, Lianyungang, China.

Yang Yang and Peng Yu have contributed a study of the interactions of the aminophenylboronic acid modified bovine serum albumin using surface plasmon resource and isothermal calorimetry, as related to biosensor development. Both are members of the China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry (Sino-French Joint Lab), Key Laboratory of Industrial Fermentation Microbiology, College of Biotechnology, Tianjin University of Science and Technology. Current research on the synthesis of PG-tb1 monovalent glycoconjugate and its immunogenicity has appeared [22]. Yang Yang and Peng Yu have described a new glycan sensor based on surface plasmon resonance and isothermal titration calorimetry. They are affiliated with College of Biotechnology, Tianjin University of Science and Technology, Tianjin, China.

I would like to thank all of the authors to this issue for their contributions. Special thanks to Binghe Wang and Markus Germann for providing the excellent reviews which are the cornerstones upon which the rest of the articles are built. The extraordinary efforts of the Editor-in-Chief Lucjan Strekowski to bring this issue to press deserves special recognition. His commitment to excellence, his willingness to give his time to editing and his patience, as well as the occasional wake-up reminders to me have resulted in this special carbohydrate issue of Heterocyclic Communications.