Solid-phase synthesis of carbohydrates presents unique challenges to synthetic chemists and currently represents one of the hottest areas of research in bioorganic chemistry. "Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries" addresses the exciting expectation that solid-phase assembly of oligosaccharides will have a fundamental impact on the field of glycobiology. This publication details the methodologies currently investigated for the attachment of carbohydrates to beads, synthesis including coupling strategies, and removal of the product from beads. With chapters written by eminent contributing authors, the material explores different synthetic strategies, glycosylation protocols, the use of solid supports versus soluble polymeric supports, and "on-resin" analytical methods. Tremendous progress in the field has set the stage for "Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries" to provide a wealth of information on such topics as: specific oligosaccharide structures used in signal transduction processes; preparation and screening of glycopeptide libraries; and solid-phase carbohydrate synthesis
PETER H. SEEBERGER is Firmenich Assistant Professor of Chemistry at the Massachusetts Institute of Technology in Cambridge, Massachusetts.
Preface. Contributors. Solid--Phase Carbohydrate Synthesis: The Early Work (W.--C. Haase & P. Seeberger). The Glycal Assembly Method on Solid Supports: Synthesis of Oligosaccharides and Glycoconjugates (P. Cirillo & S. Danishefsky). The Sulfoxide Glycosylation Method and its Application to Solid--Phase Oligosaccharide Synthesis and the Generation of Combinatorial Libraries (C. Taylor). The Use of O--Glycosyl Trichloroacetimidates for the Polymer--Supported Synthesis of Oligosaccharides (L. Knerr & R. Schmidt). Synthesis of Oligosaccharides on Solid Support Using Thioglycosides and Pentenyl Glycosides (V. Wittmann). Solid--Phase Oligosaccharide Synthesis Using Glycosyl Phosphates (W.--C. Haase, et al.). Stereoselective beta--Mannosylation on Polymer Support (Y. Ito & H. Ando). Tools for "On--Bead" Monitoring and Analysis in Solid--Phase Oligosaccharide Synthesis (W.--C. Haase, et al.). Polyethyleneglycol omega--Monomethylether (MPEG)--Supported Solution--Phase Synthesis of Oligosaccharides (J. Krepinsky & S. Douglas). Two--Direction Glycosylations for the Preparation of Libraries of Oligosaccharides (G.--J. Boons & T. Zhu). Carbohydrate Libraries in Solution Using Thioglycosides: From Multistep Synthesis to Programmable, One--Pot Synthesis (E. Simanek & C.--H. Wong). Carbohydrate Libraries by the Random Glycosylation Approach (O. Kanie & O. Hindsgaul). Solid--Phase Synthesis of Biologically Important Glycopeptides (N. Bezay & H. Kunz). Preparation and Screening of Glycopeptide Libraries (P. St. Hilaire, et al.). Index.