Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions

被引：35

作者：

Dao, DH

Okamura, M

Akasaka, T

Kawai, Y

Hida, K

Ohno, A ^{[1
]}

机构：

[1] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan

[2] Niigata Univ, Grad Sch Sci & Technol, Course Fundamental Studies & Energy Technol, Niigata 9502181, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(98)00277-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of baker's yeast with phenacyl chloride in an aqueous-organic solvent has been proven to be an effective method of inhibiting the enzymes that afford (S)-enantiomers of alpha-hydroxy esters in the reduction of alpha-keto esters. The procedure is effective for the whole-cell system to produce the (R)-product with high chemical yield and high enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2725 / 2737

页数：13

相关论文

共 37 条

[1] NEW POTENT INHIBITORS OF ANGIOTENSIN CONVERTING ENZYME [J].

ATTWOOD, MR ;

FRANCIS, RJ ;

HASSALL, CH ;

KROHN, A ;

LAWTON, G ;

NATOFF, IL ;

NIXON, JS ;

REDSHAW, S ;

THOMAS, WA .

FEBS LETTERS, 1984, 165 (02) :201-206

[2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[3]

CARPINO LA, 1988, ORG SYNTH, V6, P403

[4] Asymmetric reduction of 2-Oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures [J].

Chadha, A ;

Manohar, M ;

Soundararajan, T ;

Lokeswari, TS .

TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1571-1572

[5]

COREY EJ, 1979, TETRAHEDRON LETT, P399

[6] BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].

CSUK, R ;

GLANZER, BI .

CHEMICAL REVIEWS, 1991, 91 (01) :49-97

[7] Stereochemical control in microbial reduction. 30. Reduction of alkyl 2-oxo-4-phenylbutyrate as precursors of angiotensin converting enzyme (ACE) inhibitors [J].

Dao, DH ;

Kawai, Y ;

Hida, K ;

Hornes, S ;

Nakamura, K ;

Ohno, A ;

Okamura, M ;

Akasaka, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (02) :425-432

[8] ASYMMETRIC REDUCTION OF CARBONYL-COMPOUNDS BY YEAST .2. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES [J].

DEOL, BS ;

RIDLEY, DD ;

SIMPSON, GW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (11) :2459-2467

[9] A NOVEL AND EFFICIENT SYNTHESIS OF 6-ALKYL-7-ALKYLOXY-2,2-DIMETHYL-CHROMANS [J].

ESZENYI, T ;

TIMAR, T .

SYNTHETIC COMMUNICATIONS, 1990, 20 (20) :3219-3222

[10] BAKERS YEAST-MEDIATED PREPARATION OF OPTICALLY-ACTIVE ARYL ALCOHOLS AND DIOLS FOR THE SYNTHESIS OF CHIRAL HYDROXY-ACIDS [J].

FERRABOSCHI, P ;

GRISENTI, P ;

MANZOCCHI, A ;

SANTANIELLO, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09) :2469-2474

← 1 2 3 4 →