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Artificial Cysteine S‐Glycosylation Induced by Per‐O‐Acetylated Unnatural Monosaccharides during Metabolic Glycan Labeling
Author(s) -
Qin Wei,
Qin Ke,
Fan Xinqi,
Peng Linghang,
Hong Weiyao,
Zhu Yuntao,
Lv Pinou,
Du Yifei,
Huang Rongbing,
Han Mengting,
Cheng Bo,
Liu Yuan,
Zhou Wen,
Wang Chu,
Chen Xing
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711710
Subject(s) - monosaccharide , glycosylation , glycan , chemistry , acetylation , biochemistry , cysteine , enzyme , glycoprotein , gene
The unexpected, non‐enzymatic S‐glycosylation of cysteine residues in various proteins by per‐O‐acetylated monosaccharides is described. This artificial S‐glycosylation greatly compromises the specificity and validity of metabolic glycan labeling in living cells by per‐O‐acetylated azido and alkynyl sugars, which has been overlooked in the field for decades. It is demonstrated that the use of unacetylated unnatural sugars can avoid the artifact formation and a corrected list of O‐GlcNAcylated proteins and O‐GlcNAc sites in HeLa cells has been assembled by using N ‐azidoacetylgalactosamine (GalNAz).