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Artificial Cysteine S-Glycosylation Induced by Per-O-Acetylated Unnatural Monosaccharides during Metabolic Glycan Labeling.

Wei QinKe QinXinqi FanLinghang PengWeiyao HongYuntao ZhuPinou LvYifei DuRongbing HuangMengting HanBo ChengYuan LiuWen ZhouChu WangXing Chen
Published in: Angewandte Chemie (International ed. in English) (2018)
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).
Keyphrases
  • living cells
  • fluorescent probe
  • cell cycle arrest
  • single molecule
  • induced apoptosis
  • cell death
  • cell surface
  • hydrogen peroxide
  • computed tomography
  • cell proliferation