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Literature DB >> 31875401

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

Qingfei Zheng¹, Igor Maksimovic^1,2, Akhil Upad¹, David Guber^1,3, Yael David^1,2,4,5.

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.

Entities: CellLine Chemical Disease Gene Species

Year: 2020 PMID： 31875401 PMCID： PMC8018604 DOI： 10.1021/acs.joc.9b02504

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

27 in total

1. Discovery and Optimization of Inhibitors of the Parkinson's Disease Associated Protein DJ-1.

Authors: Shinya Tashiro; Jose M M Caaveiro; Makoto Nakakido; Aki Tanabe; Satoru Nagatoishi; Yasushi Tamura; Noriyuki Matsuda; Dali Liu; Quyen Q Hoang; Kouhei Tsumoto
Journal: ACS Chem Biol Date: 2018-08-15 Impact factor: 5.100

Review 2. Chemical biology approaches for studying posttranslational modifications.

Authors: Aerin Yang; Kyukwang Cho; Hee-Sung Park
Journal: RNA Biol Date: 2017-09-21 Impact factor: 4.652

3. Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones.

Authors: Guo-Chao Chu; Man Pan; Jiabin Li; Sanling Liu; Chong Zuo; Ze-Bin Tong; Jing-Si Bai; Qingyue Gong; Huasong Ai; Jian Fan; Xianbin Meng; Yi-Chao Huang; Jing Shi; Haiteng Deng; Changlin Tian; Yi-Ming Li; Lei Liu
Journal: J Am Chem Soc Date: 2019-02-13 Impact factor: 15.419

Review 4. DJ-1 as a human oncogene and potential therapeutic target.

Authors: Ji Cao; Siyue Lou; Meidan Ying; Bo Yang
Journal: Biochem Pharmacol Date: 2014-12-11 Impact factor: 5.858

Review 5. Readout of epigenetic modifications.

Authors: Dinshaw J Patel; Zhanxin Wang
Journal: Annu Rev Biochem Date: 2013 Impact factor: 23.643

Review 6. Methylglyoxal, the dark side of glycolysis.

Authors: Igor Allaman; Mireille Bélanger; Pierre J Magistretti
Journal: Front Neurosci Date: 2015-02-09 Impact factor: 4.677

7. Protein arginine deiminase 4 antagonizes methylglyoxal-induced histone glycation.

Authors: Qingfei Zheng; Adewola Osunsade; Yael David
Journal: Nat Commun Date: 2020-06-26 Impact factor: 14.919

8. Histone glycation: Linking metabolic perturbation with epigenetic misregulation in cancer.

Authors: Xiayao Diao
Journal: AIMS Genet Date: 2019-06-04

9. Methylglyoxal, a glycolysis side-product, induces Hsp90 glycation and YAP-mediated tumor growth and metastasis.

Authors: Marie-Julie Nokin; Florence Durieux; Paul Peixoto; Barbara Chiavarina; Olivier Peulen; Arnaud Blomme; Andrei Turtoi; Brunella Costanza; Nicolas Smargiasso; Dominique Baiwir; Jean L Scheijen; Casper G Schalkwijk; Justine Leenders; Pascal De Tullio; Elettra Bianchi; Marc Thiry; Koji Uchida; David A Spiegel; James R Cochrane; Craig A Hutton; Edwin De Pauw; Philippe Delvenne; Dominique Belpomme; Vincent Castronovo; Akeila Bellahcène
Journal: Elife Date: 2016-10-19 Impact factor: 8.140

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

1. Discovery and Optimization of Inhibitors of the Parkinson's Disease Associated Protein DJ-1.

Review 2. Chemical biology approaches for studying posttranslational modifications.

3. Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones.

Review 4. DJ-1 as a human oncogene and potential therapeutic target.

Review 5. Readout of epigenetic modifications.

Review 6. Methylglyoxal, the dark side of glycolysis.

7. Protein arginine deiminase 4 antagonizes methylglyoxal-induced histone glycation.

8. Histone glycation: Linking metabolic perturbation with epigenetic misregulation in cancer.

9. Methylglyoxal, a glycolysis side-product, induces Hsp90 glycation and YAP-mediated tumor growth and metastasis.

Review 10. Post-Translational Modifications of Protein Backbones: Unique Functions, Mechanisms, and Challenges.

1. Chemical Labeling and Enrichment of Histone Glyoxal Adducts.

2. An Azidoribose Probe to Track Ketoamine Adducts in Histone Ribose Glycation.

Review 3. A chemical field guide to histone nonenzymatic modifications.

Review 4. Non-enzymatic Covalent Modifications as a New Chapter in the Histone Code.

5. Protein arginine deiminase 4 antagonizes methylglyoxal-induced histone glycation.

Review 6. Non-enzymatic covalent modifications: a new link between metabolism and epigenetics.

Review 7. Tumor microbiome metabolism: A game changer in cancer development and therapy.