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A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol–Ene Coupling
Author(s) -
Dondoni Alessandro,
Massi Alessandro,
Nanni Paolo,
Roda Aldo
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901746
Subject(s) - thiol , bovine serum albumin , cysteine , peptide , chemistry , glycosylation , cystine , ene reaction , residue (chemistry) , chemical ligation , native chemical ligation , combinatorial chemistry , biochemistry , stereochemistry , enzyme
Photoclick with proteins : Two cysteine containing peptides and the natural protein bovine serum albumin (BSA) were glycosylated (see scheme) by an alkenyl glycoside upon irradiation with visible light in the presence of a sensitizer (click thiol–ene coupling). The hyperglycosylation of BSA involved the cysteine free SH and two SH groups derived from selective photocleavage of a cystine residue.