期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 9, 期 24, 页码 5997-6006出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200305290
关键词
carbohydrates; chemoselective; ligation; dehydropeptide; glycopeptides; mucin
资金
- NIGMS NIH HHS [GM58833, GM58822] Funding Source: Medline
A chemoselective strategy for oligosaccharide-peptide ligation is described in which alpha-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, T-N, 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 alpha-anomeric configuration.
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