Glycomimetics : modern synthetic methodologies

Bibliographic Information

Glycomimetics : modern synthetic methodologies

René Roy, editor ; sponsored by the ACS Division of Carbohydrate Chemistry

(ACS symposium series, 896)

American Chemical Society, c2005

Available at  / 7 libraries

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Note

"This book is the result of combined symposia held under the auspices of the American Chemical Society (ACS). The symposia were held at the 225th National Meeting in New Orleans, Louisiana on March 23-27, 2003"--Pref

Includes bibliographical references and indexes

Description and Table of Contents

Description

Modern Synthetic Methodologies Toward Glycomimetics contains 10 chapters describing the syntheses of natural and non-natural glycomimetics using modern transition metal catalyzed reactions. This book also contains several experimental details allowing the readers to get familiar with such intricate reactions using complex alkylidene carbenoids, samarium diodide, dicobalt octacarbonyl alkyne cyclotrimerization, and the like. The descripitions of biologically active carbohydrates are elegantly detailed. A new solution-phase glycopeptide synthesis using unprotected glycosyl amino acids as phase-tags is also described. Important strategies into the design of complex sialic acid C-saccharides, aryl C-glycosides, and conformationally restricted analogs of the important sialyl Lewis X are discussed. Tethering of carbohydrate residues through ester bonds and applications of the Tebbe's methylenation and either ring closing metathesis or intramolecular C-glycosidations are used to provide novel carbohydrate analogs.

Table of Contents

Preface 1: Alois Furstner: Reflections upon Olefin Metathesis in Carbohydrate Chemistry 2: Maarten H.D. Postema, Jared L. Piper, Lei Liu, Venu Komanduri, and Russell L. Betts: Synthesis of Stable Carbohydrate Mimetics 3: Chi-Chang Chen, Dino Ress, and Robert J. Linhart: Synthesis of Neu5Ac, KDN, and KDO C-Glycosides 4: Emma R. Palmacci, Holger Herzner, and Peter H. Seeberger: Synthesis of C-Glycosides with Glycosyl Phosphates 5: Kathlyn A. Parker: Aryl C-Glycosides by the Reverse Polarity Approach 6: Peter S. Belica, Alain Berthold, Nikki Charles, Guangwu Chen, Ajit Parhi, Paolo Pasetto, Jun Pu, Guangli Yang, and Richard W. Franck: The Ramberg-Backlund Way to C-Glyucosides 7: R.W. Denton, and D.R. Mootoo: Conformationally Restrained C-Glycoside Probes for Sialyl Lewis X-Selectin Recognition 8: Rene Roy, M. Corazon Trono, and Denis Giguere: Effects of Linker Rigidity and Orientation of Mannoside Clusters for Multivalent Interactions with Proteins 9: Vincent Bouvet, and Robert N. Ben: Antifreeze Glycoprotein Analogs: Synthesis, In Vitro Testing, and Applications 10: Zhongwu Guo: Unprotected Oligosaccharides as Phase Tags for Solution-Phase Glycoprotein Synthesis with Solid-Phrase Workup Author Index Subject Index

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