Glyoxalase-based toolbox for the enantioselective synthesis of a-hydroxy carboxylic acids

Mussa Yedigenov; Niyaz Amire; Aizat Abdirassil; Tomiris Mulikova; Azamat Begenov; Anniina Kiesilä; Anatoly A. Peshkov; Vsevolod A. Peshkov; Darkhan Utepbergenov

doi:10.1039/d3ob02098c

Glyoxalase-based toolbox for the enantioselective synthesis of a-hydroxy carboxylic acids

Mussa Yedigenov, Niyaz Amire, Aizat Abdirassil, Tomiris Mulikova, Azamat Begenov, Anniina Kiesilä, Anatoly A. Peshkov, Vsevolod A. Peshkov, Darkhan Utepbergenov

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

We report highly enantioselective synthesis of l-a-hydroxy carboxylic acids (l-aHCAs) via enzymatic intramolecular Cannizzaro reaction of (hetero)aryl glyoxals in the presence of glutathione-independent human glyoxalase DJ-1. Combined with the optimized synthesis of d-aHCAs using glyoxalases I and II, this approach offers a general, scalable and operationally simple access to both enantiomers of a-hydroxy acids in moderate to excellent yields with uniformly high enantioselectivity.

Original language	English
Journal	Organic and Biomolecular Chemistry
DOIs	https://doi.org/10.1039/d3ob02098c
Publication status	Accepted/In press - 2024

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Glyoxalase-based toolbox for the enantioselective synthesis of a-hydroxy carboxylic acids",

abstract = "We report highly enantioselective synthesis of l-a-hydroxy carboxylic acids (l-aHCAs) via enzymatic intramolecular Cannizzaro reaction of (hetero)aryl glyoxals in the presence of glutathione-independent human glyoxalase DJ-1. Combined with the optimized synthesis of d-aHCAs using glyoxalases I and II, this approach offers a general, scalable and operationally simple access to both enantiomers of a-hydroxy acids in moderate to excellent yields with uniformly high enantioselectivity.",

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note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

year = "2024",

doi = "10.1039/d3ob02098c",

language = "English",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Glyoxalase-based toolbox for the enantioselective synthesis of a-hydroxy carboxylic acids

AU - Yedigenov, Mussa

AU - Amire, Niyaz

AU - Abdirassil, Aizat

AU - Mulikova, Tomiris

AU - Begenov, Azamat

AU - Kiesilä, Anniina

AU - Peshkov, Anatoly A.

AU - Peshkov, Vsevolod A.

AU - Utepbergenov, Darkhan

PY - 2024

Y1 - 2024

N2 - We report highly enantioselective synthesis of l-a-hydroxy carboxylic acids (l-aHCAs) via enzymatic intramolecular Cannizzaro reaction of (hetero)aryl glyoxals in the presence of glutathione-independent human glyoxalase DJ-1. Combined with the optimized synthesis of d-aHCAs using glyoxalases I and II, this approach offers a general, scalable and operationally simple access to both enantiomers of a-hydroxy acids in moderate to excellent yields with uniformly high enantioselectivity.

AB - We report highly enantioselective synthesis of l-a-hydroxy carboxylic acids (l-aHCAs) via enzymatic intramolecular Cannizzaro reaction of (hetero)aryl glyoxals in the presence of glutathione-independent human glyoxalase DJ-1. Combined with the optimized synthesis of d-aHCAs using glyoxalases I and II, this approach offers a general, scalable and operationally simple access to both enantiomers of a-hydroxy acids in moderate to excellent yields with uniformly high enantioselectivity.

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DO - 10.1039/d3ob02098c

M3 - Article

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AN - SCOPUS:85185334055

SN - 1477-0520

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

Glyoxalase-based toolbox for the enantioselective synthesis of a-hydroxy carboxylic acids

Abstract

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