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

共 50 条

[21] Chemoselective allylic addition of allyltrichlorosilane to α-oxocarboxylic acids:: synthesis of tertiary α-hydroxy carboxylic acids
Wang, Z
Xu, GY
Wang, DJ
Pierce, ME
Confalone, PN
TETRAHEDRON LETTERS, 2000, 41 (23) : 4523 - 4526
[22] Enantioselective synthesis of α-hydroxy-β-amino acids from α-amino acids mediated by sulfoxides
Sanchez-Obregon, Ruben
Salgado, Fernando
Ortiz, Benjamin
Diaz, Eduardo
Yuste, Francisco
Walls, Fernando
Ruano, Jose L. Garcia
TETRAHEDRON, 2007, 63 (42) : 10521 - 10527
[23] Calixarene based chiral solvating agents for α-hydroxy carboxylic acids
Bozkurt, Selahattin
JOURNAL OF MOLECULAR STRUCTURE, 2013, 1048 : 113 - 120
[24] Total synthesis of natural tert-alkylamino hydroxy carboxylic acids
Kang, SH
Kang, SY
Lee, HS
Buglass, AJ
CHEMICAL REVIEWS, 2005, 105 (12) : 4537 - 4558
[25] SYNTHESIS OF SOME METHOXY AND HYDROXY-PHENAZINE-1-CARBOXYLIC ACIDS
BROOKE, PK
CHALLAND, SR
FLOOD, ME
HERBERT, RB
HOLLIMAN, FG
IBBERSON, PN
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (21): : 2248 - 2251
[26] ENANTIOSELECTIVE SYNTHESIS OF 1-SUBSTITUTED TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACIDS
CZARNOCKI, Z
SUH, D
MACLEAN, DB
HULTIN, PG
SZAREK, WA
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (05): : 1555 - 1561
[27] An inexpensive carbohydrate derivative used as a chiral auxiliary in the synthesis of α-hydroxy carboxylic acids
Yu, HW
Ballard, CE
Boyle, PD
Wang, BH
TETRAHEDRON, 2002, 58 (38) : 7663 - 7679
[28] NEW SYNTHESIS OF OLEFINS FROM BETA-HYDROXY CARBOXYLIC-ACIDS
HARA, S
TAGUCHI, H
YAMAMOTO, H
NOZAKI, H
TETRAHEDRON LETTERS, 1975, (19-2) : 1545 - 1548
[29] AN IMPROVED SYNTHESIS OF 4'-HYDROXY AND 4'-METHOXYBIPHENYL-2-CARBOXYLIC ACIDS
ESTENNE, G
DODEY, P
RENAUT, P
LECLERC, G
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1995, 27 (04) : 500 - 503
[30] Diastereoselective synthesis of anti-3-hydroxy-2-trifluoromethyl carboxylic acids
Ramachandran, P. Veeraraghavan
Otoo, Barnabas
Chanda, Prem B.
TETRAHEDRON LETTERS, 2015, 56 (23) : 3019 - 3022

← 1 2 3 4 5 →