Synthesis of an alkynyl methylglyoxal probe to investigate nonenzymatic histone glycation Journal Article


Authors: Zheng, Q.; Maksimovic, I.; Upad, A.; Guber, D.; David, Y.
Article Title: Synthesis of an alkynyl methylglyoxal probe to investigate nonenzymatic histone glycation
Abstract: Methylglyoxal (MGO) is a reactive dicarbonyl metabolite that modifies histones in vivo and induces changes in chromatin structure and function. Here we report the synthesis and application of a chemical probe for investigating MGO-glycation. A two-step synthesis of a Cu-click compatible alkynyl oxoaldehyde probe (AlkMGO) via sequential Dess-Martin and Riley oxidations is presented. This synthesis elevates the accessibility and utility of an important tool for tracking, enriching, and studying MGO-glycation to aid in understanding its underlying biochemical functions. Copyright © 2019 American Chemical Society.
Keywords: controlled study; unclassified drug; human cell; proteins; in vitro study; histone; histone h3; glycosylation; probes; biochemistry; histone h2a; histone h2b; oxidation; copper; synthesis; chromatin structure; click chemistry; histone h4; metabolites; alkynyl group; human; article; biochemical functions; methylglyoxal; chemical probes; glycation; alkynyls; non-enzymatic; two-step synthesis; alkynyl methylglyoxal probe; dess martin oxidation; riley oxidation
Journal Title: Journal of Organic Chemistry
Volume: 85
Issue: 3
ISSN: 0022-3263
Publisher: American Chemical Society  
Date Published: 2020-02-07
Start Page: 1691
End Page: 1697
Language: English
DOI: 10.1021/acs.joc.9b02504
PUBMED: 31875401
PROVIDER: scopus
PMCID: PMC8018604
DOI/URL:
Notes: Article -- Export Date: 1 April 2020 -- Source: Scopus
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MSK Authors
  1. Qingfei Zheng
    8 Zheng
  2. Akhil Upad
    2 Upad
  3. David Guber
    1 Guber