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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.

SUBMITTER: Zheng Q

PROVIDER: S-EPMC8018604 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Synthesis of an Alkynyl Methylglyoxal Probe to Investigate Nonenzymatic Histone Glycation.

Zheng Qingfei Q Maksimovic Igor I Upad Akhil A Guber David D David Yael Y

The Journal of organic chemistry 20200107 3

Methylglyoxal (MGO) is a reactive dicarbonyl metabolite that modifies histones <i>in vivo</i> 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 stud ...[more]

PMID: 31875401

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