Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 14, Issue 11, Pages 2835-2838Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2004.03.050
Keywords
glycopeptide; carbohydrate; dynamic combinatorial library; disulfide-linking chemistry
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We report here that disulfide-linked dynamic glycopeptide libraries can be constructed from 1-thiosugar and cysteine-rich oligopeptide building blocks upon gentle air oxidation of a slightly basic (pH7.8) aqueous solution thereof. A mixture of 1-thiogalactose and two oligopeptides H2N-CysGlyCysGly-CO2H and H2N-GlyCycCysGlyGly-CO2H, for example, affords a poorly HPLC-resolved disulfide library composed of various sugar-peptide conjugates and cyclic peptides, at least 10 of which can be identified by ESI mass spectrometry. The building components of disulfide members are exchangeable with each other in the presence of dithiothreitol as an initiator to allow dynamic equilibration. A preliminary SPR examination shows that the thiogalactose-derived library indeed contains active divalent galactoside species capable of cross-linking peanut lectin molecules. (C) 2004 Elsevier Ltd. All rights reserved.
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