Anomeric Fatty Acid Functionalization Prevents Nonenzymatic S-Glycosylation by Monosaccharide Metabolic Chemical Reporters

Nichole J. Pedowitz, Emma G. Jackson, Justin M. Overhulse, Charles E. McKenna, Jennifer J. Kohler, Matthew R. Pratt

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Metabolic chemical reports have fundamentally changed the way researchers study glycosylation. However, when administered as per-O-acetylated sugars, reporter molecules can participate in nonspecific chemical labeling of cysteine residues termed S-glycosylation. Without detailed proteomic analyses, these labeling events can be indistinguishable from bona fide enzymatic labeling convoluting experimental results. Here, we report a solution in the synthesis and characterization of two reporter molecules functionalized at the anomeric position with hexanoic acid: 1-Hex-GlcNAlk and 1-Hex-6AzGlcNAc. Both reporters exhibit robust labeling over background with negligible amounts of nonspecific chemical labeling in cell lysates. This strategy serves as a template for the design of future reporter molecules allowing for more reliable interpretation of results.

Original languageEnglish (US)
Pages (from-to)1924-1929
Number of pages6
JournalACS chemical biology
Volume16
Issue number10
DOIs
StatePublished - Oct 15 2021

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine

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