Oligosaccharide–Peptide Ligation of Glycosyl Thiolates with Dehydropeptides: Synthesis of S‐Linked Mucin‐Related Glycopeptide Conjugates
- 11 December 2003
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (24) , 5997-6006
- https://doi.org/10.1002/chem.200305290
Abstract
A chemoselective strategy for oligosaccharide–peptide ligation is described in which α-thio analogues of mucin-related glycoconjugates can be readily accessed through site-selective conjugate addition of complex oligosaccharide thiolates to dehydroalanine-containing peptides. The efficiency of the ligation is highlighted by the rapid convergent assembly of thio-isosteres of the four tumor-associated carbohydrate antigens, TN, T, STN, and 2,6-ST, as a pair of diastereoisomers at the newly formed cysteine stereocenter. The process proceeds in high yield and with complete retention of the α-anomeric configuration.Keywords
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