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

The Journal of organic chemistry (2019-12-26)
Qingfei Zheng, Igor Maksimovic, Akhil Upad, David Guber, Yael David
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Azide-PEG3-biotin conjugate
Sigma-Aldrich
Cy5-azide, 95% (HPLC)