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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