Handbook Of Chemical Glycosylation - Advances In Stereoselectivity And Therapeutic Relevance

Since carbohydrate oligomers are still a challenge in synthetic chemistry, this book on recent developments fulfils a great need. Covering the chemistry necessary to synthesize exact copies of these structures, top authors from all around the world comprehensively deal with synthesis from anomeric halides, from miscellaneous glycosyl donors, and by indirect and special methods, as well as 1-oxygen-and 1-sulfur-substituted derivatives. They demonstrate the best approach for the stereoselective formation of the intermonomeric bond, making this essential reading for every biochemist working in biosynthesis, the exploration of biopathways and vaccines.

Born in 1965, Alexei Demchenko gained his MSc in chemical engineering from Mendeleev University of Chemical Technology, Russia, in 1988, before joining the Zelinski Institute of Organic Chemistry, at the Russian Academy of Sciences, Moscow. It was here, under Professor Kochetkov, that he took his first steps in researching carbohydrate synthesis. In 1993 he was awarded a PhD for his work on the development of thiocyanate methodology for stereospecific glycosylation and, after two post-doctoral years under Kochetkov, he joined Geert-Jan Boons' group at the University of Birmingham, UK, as a BBSRC post-doctoral research fellow. In 1998 he moved with Professor Boons to the Complex Carbohydrate Research Center at the University of Georgia as a research associate, where his research focused on the synthesis of complex oligosaccharides for immunological studies and the exploration of chemical O-sialylation. In 2001 he joined the University of Missouri St. Louis as an assistant professor of chemistry and biochemistry. Professor Demchenko is a recipient of the CAREER award from the National Science Foundation, and has co-authored over 50 articles, reviews, and book chapters. His current research interests are in the field of synthetic carbohydrate chemistry.

Preface.

List of Contributors.

1 General Aspects of the Glycosidic Bond Formation (Alexei V. Demchenko).

1.1 Introduction.

1.2 Major Types of O-Glycosidic Linkages.

1.3 Historical Development: Classes of Glycosyl Donors.

1.4 General Reaction Mechanism.

1.5 Anomeric Effects.

1.6 Stereoselectivity of Glycosylation.

1.7 Special Cases of Glycosylation.

1.8 Glycosylation and Oligosaccharide Sequencing.

1.9 Conclusions and Outlook.

2 Glycoside Synthesis from Anomeric Halides.

2.1 Glycosyl Fluorides (Shin-ichiro Shoda).

2.2 Glycosyl Chlorides, Bromides and Iodides (Suvarn S. Kulkarni, Jacquelyn Gervay-Hague).

3 Glycoside Synthesis from 1-Oxygen Substituted Glycosyl Donors.

3.1 Hemiacetals and O-Acyl/Carbonyl Derivatives (Daniel A. Ryan, David Y. Gin).

3.2 Glycoside Synthesis from 1-Oxygen-Substituted Glycosyl Imidates (Xiangming Zhu, Richard R. Schmidt).

3.3 Anomeric Transglycosylation (Kwan-Soo Kim, Heung-Bae Jeon).

3.4 Phosphates, Phosphites and Other O–P Derivatives (Seiichi Nakamura, Hisanori Nambu, Shunichi Hashimoto).

4 Glycoside Synthesis from 1-Sulfur/Selenium-Substituted Derivatives.

4.1 Thioglycosides in Oligosaccharide Synthesis (Wei Zhong, Geert-Jan Boons).

4.2 Sulfoxides, Sulfimides and Sulfones (David Crich, Albert A. Bowers).

4.3 Xanthates, Thioimidates and Other Thio Derivatives (Wiesław Szeja, Grzegorz Grynkiewicz).

4.4 Selenoglycosides (Robert A. Field).

5 Other Methods for Glycoside Synthesis.

5.1 Orthoesters and Related Derivatives (Bert Fraser-Reid, J. Cristóbal López).

5.2 Other Methods for Glycoside Synthesis: Dehydro and Anhydro Derivatives (David W. Gammon, Bert F. Sels).

5.3 Miscellaneous Glycosyl Donors (Kazunobu Toshima).

5.4 The Twenty First Century View of Chemical O-Glycosylation (Thomas Ziegler).

Index.