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

Результат исследований › рецензирование

4 Цитирования (Scopus)

Аннотация

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.

Язык оригинала	English
Журнал	Organic and Biomolecular Chemistry
DOI	https://doi.org/10.1039/d3ob02098c
Состояние	Accepted/In press - 2024

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d3ob02098c

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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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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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