Utilizing Staudinger Ligation for the Synthesis of Glycoamino Acid Building Blocks and Other Glycomimetics

✍ Scribed by Alexander Schierholt; Harun A. Shaikh; Jörn Schmidt-Lassen; Thisbe K. Lindhorst

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 212 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200900437

✦ Synopsis

Abstract

The synthesis of amide‐linked glycomimetics is of interest in the glycosciences as they represent a typical linkage in biologically important glycoconjugates. We have addressed the synthesis of three types of N‐glycosyl amide architectures, which were targeted using Staudinger ligation. This facile method has allowed us to synthesize a collection of N‐glycosyloctanamides, N‐glycosyloxyethyl amino acids and multivalent glycoclusters. The last two classes represent molecules that can be used as building blocks in solid‐phase peptide synthesis for the preparation of multivalent glycoconjugates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)