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

被引：5

作者：

Yedigenov, Mussa ^{[1
,3
]}

Amire, Niyaz ^{[1
,4
]}

Abdirassil, Aizat ^{[1
,5
]}

Mulikova, Tomiris ^{[1
,6
]}

Begenov, Azamat ^{[1
]}

Kiesilae, Anniina ^{[2
]}

Peshkov, Anatoly A. ^{[1
]}

Peshkov, Vsevolod A. ^{[1
,2
]}

Utepbergenov, Darkhan ^{[1
]}

机构：

[1] Nazarbayev Univ, Sch Sci & Humanities, Dept Chem, 53 Kabanbay Batyr Ave, Astana 010000, Kazakhstan

[2] Univ Jyvaskyla, Dept Chem, Survontie 9 B, FI-40500 Jyvaskyla, Finland

[3] Max Planck Inst Med Res, Max Planck Sch Matter Life, Jahnstr 29, D-69120 Heidelberg, Germany

[4] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

[5] Univ Pittsburgh, Ctr Pharmacogenet, Sch Pharm, 3501 Terrace St, Pittsburgh, PA 15261 USA

[6] Univ N Carolina, Sch Med, Dept Biochem & Biophys, 120 Mason Farm Rd, Chapel Hill, NC 27599 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 13期

关键词：

KINETIC RESOLUTION; (R)-(-)-MANDELIC ACID; HIGHLY EFFICIENT; KETO ACIDS; DJ-1; ENZYME; METHYLGLYOXAL; DEHYDROGENASE; CONVERSION; NITRILASE;

D O I：

10.1039/d3ob02098c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report highly enantioselective synthesis of l-alpha-hydroxy carboxylic acids (l-alpha HCAs) 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-alpha HCAs using glyoxalases I and II, this approach offers a general, scalable and operationally simple access to both enantiomers of alpha-hydroxy acids in moderate to excellent yields with uniformly high enantioselectivity. Glyoxalases DJ-1 and GlxI/II were used for the enantioselective conversion of 13 (hetero)aryl glyoxals to l- and d-alpha-hydroxy carboxylic acids, respectively.

引用

页数：6

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