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Utilizing Staudinger Ligation for the Synthesis of Glycoamino Acid Building Blocks and Other Glycomimetics
Author(s) -
Schierholt Alexander,
Shaikh Harun A.,
SchmidtLassen Jörn,
Lindhorst Thisbe K.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900437
Subject(s) - chemistry , glycoconjugate , glycosyl , combinatorial chemistry , solid phase synthesis , amide , peptide synthesis , combinatorial synthesis , peptide , staudinger reaction , stereochemistry , organic chemistry , biochemistry
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)
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