Open AccessSynthesis of an Alkynyl Methylglyoxal Probe to Investigate Nonenzymatic Histone Glycation
Author(s) -
Qingfei Zheng,
Igor Maksimovic,
Akhil Upad,
David Guber,
Yael David
Publication year - 2019
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b02504
Subject(s) - methylglyoxal , glycation , chemistry , histone , bioorthogonal chemistry , biochemistry , chromatin , in vivo , metabolite , click chemistry , combinatorial chemistry , enzyme , biology , dna , microbiology and biotechnology , receptor
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.