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Synthesis of Thioether‐Linked Analogues of the 2,3‐Sialyl‐TF and MECA‐79 Antigens: Mucin‐Type Glycopeptides Associated with Cancer and Inflammation
Author(s) -
Marcaurelle Lisa A.,
Pratt Matthew R.,
Bertozzi Carolyn R.
Publication year - 2003
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200390036
Subject(s) - glycopeptide , chemistry , peptide , peptide synthesis , ligand (biochemistry) , glycoprotein , thioether , antigen , solid phase synthesis , combinatorial chemistry , biochemistry , amino acid , stereochemistry , computational biology , biology , receptor , genetics , antibiotics
Sulfur linkages: A strategy for the synthesis of a glycosylated analogue of a 17 amino acid fragment of the P‐selectin glycoprotein ligand‐1 (PSGL‐1) is reported. A 2‐azido‐3‐thiogalctose‐Thr analogue was incorporated into the peptide by 9‐fluorenylmethoxycarbonyl (Fmoc)‐based solid‐phase peptide synthesis, and higher‐order oligosaccharides corresponding to the 2,3‐sialyl‐TF (STF) and MECA‐79 antigens were generated by alkylation of the corresponding 3‐thioGalNAc with N ‐bromoacetamido sugars (see scheme).