Frontiers in Modern Carbohydrate Chemistry

by Alexei V. Demchenko

Overview

Recent understanding of the involvement of carbohydrate molecules and conjugates in many vital biological processes and, consequently, the appreciation of their tremendous therapeutic potential has stimulated the development of new methods for the synthesis of this class of compounds. The main efforts in the field of synthetic carbohydrate chemistry have been focused on the development of new glycosylation methodologies and convergent strategies for oligosaccharide synthesis, in which the number of synthetic and purification steps is reduced. As a result, many efficient approaches have been developed both on the solid phase and in solution. This book brings together leading specialists working in the emerging areas of chemistry and biology on specific topics in the area of carbohydrates. As a result, the book will be of great interest to scientists solving carbohydrate puzzles in many diverse areas of research.

Product Details

ISBN-13:	9780841239708
Publisher:	American Chemical Society
Publication date:	03/19/2007

About the Author

University of Missouri-St. Louis

Table of Contents

1. Synthesis of modified monosaccharides as biological probes and therapeutic agents
1.1. Synthesis of 9-Substituted Sialic Acids As Probes for CD22-Ligand Interactions on B cells, Shoufa Han, Brian E. Collins, and James C. Paulso
1.2. Uncommon Sugars and Their Conjugates to Natural Products, Wenlan Chen, Guisheng Zhang, Lizhi Zhu, Lanyan Fang, Xianhua Cao, James Kedenburg, Jie Shen, Duxin Sun,* and Peng George Wang
1.3. Plant Cell Wall Glycans: Chemical Synthesis of the Branched Sugar Aceric Acid, Sergey A. Nepogodiev,* Nigel A Jones, and Robert A. Field
1.4. Iodoamidation of Glycals: A Facile Preparation of 2-Deoxy-N-glycosylamides, Cecilia H. Marzabadi* and Michael DeCastro
2. New methods for stereoselective O-glycosylation
2.1. Stereocontrolled Glycosylation: Recent Advances: ?-D-Rhamnosides and ?-D-Mannans, David Crich
2.2. Stereoselective Glycosylations Using Chiral Auxiliaries, Jin-Hwan Kim, Hai Yang, Geert-Jan Boons
2.3. Protecting Groups in Carbohydrate Chemistry Profoundly Influence All Selectivities in Glycosyl Couplings, Bert Fraser-Reid,K. N. Jayaprakash, J. Cristóbal López,Ana M. Gómez, Clara Uriel
2.4. Synthesis of N-5-Derivatives of Neuraminic Acid and their Application as Sialosyl Donors, Cristina De Meo
3. New strategies for convergent oligosaccharide synthesis
3.1. 2'-Carboxybenzylglycosides: A Novel Type of Glycosyl Donors and Their Application to Oligosaccharide Synthesis, Kwan Soo Kim and Heung Bae Jeon
3.2. Oligosaccharide Synthesis with Glycosyl Phosphates, Jeroen D. C. Codée and Peter H. Seeberger
3.3. Glycosyl thioimidates as versatile glycosyl donors for stereoselective O-glycosylation and convergent oligosaccharide synthesis, Papapida Pornsuriyasak, Medha N. Kamat, and Alexei V. Demchenko*
3.4. Sequential glycosylation strategies; a focus on thioglycosides as donors and acceptors, G. A. van der Marel,* L. J. van den Bos, H. S. Overkleeft, R. E. J. N. Litjens, J. D. C. Codée
3.5. New Aspects of Glycoside Bond Formation - Solid Phase Oligosaccharide Synthesis, Richard R. Schmidt, Simon Jonke, and Ke-gang Liu
4. Chemical and enzymatic synthesis of therapeutically significant complex glycostructures
4.1. Synthesis of carbohydrate antigens related to Shigella dysenteriae type 1 and of their protein conjugates, Vince Pozsgay and Joanna Kubler-Kielb
4.2. Enzymatic Synthesis of Glycosaminoglycans: Improving on Nature, Fikri Y. Avci, Paul L. DeAngelis, Jian Liu, Robert J. Linhardt
4.3. The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi trypomastigote mucins: exploration of ester and acetal type permanent protecting groups, Dmitry V. Yashunsky, Vladimir S. Borodkin, Philip G. McGivern, Michael A. J. Ferguson and Andrei V. Nikolaev*
4.4. Glycodiversification for the Synthesis of Neomycin and Kanamycin Class Aminoglycoside Antibiotics, Jinhua Wang and Cheng-Wei Tom Chang
n 4.5 Convergent N-Glycopeptide Synthesis, Katja Michae
5. Special topics of modern glycochemistry
5.1. Targeting Galectin-1 with Self-Assembled Multivalent Pseudopolyrotaxanes, Jason M. Belitsky and J. Fraser Stoddart
5.2. De Novo Synthesis of Biofunctional Carbohydrate-Encapsulated Quantum Dots, Sergei A. Svarovsky and Joseph J. Barchi, Jr.