Highly stereoselective reduction of 4-Aryl-2-oxo but-3-enoic carboxylic esters by plant cell culture of Daucus carota

被引：40

作者：

Baskar, B

Ganesh, S

Lokeswari, TS

Chadha, A ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

[2] SPIC Sci Fdn, Div Biotechnol, Madras 600032, Tamil Nadu, India

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2004年 / 27卷 / 01期

关键词：

Daucus carota; plant tissue culture; asymmetric reduction; alpha-hydroxy beta; gamma-unsaturated arylidine esters;

D O I：

10.1016/j.molcatb.2003.09.004

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A highly enantioselective preparation (92-99% enantiomeric excess, 100% conversion) of various 4-aryl-2-hydroxy but-3-enoic carboxylic acid esters from the corresponding 4-phenyl-2-keto but-3-enoic acid esters mediated by plant cell cultures of Daucus carota under mild and environmentally benign conditions in aqueous medium is described. (C) 2003 Elsevier B.V All rights reserved.

引用

收藏

页码：13 / 17

页数：5

相关论文

共 35 条

[21] BIOTRANSFORMATION OF SOME KETO ESTERS THROUGH THE CONSECUTIVE REUSE OF IMMOBILIZED NICOTIANA-TABACUM CELLS [J].

NAOSHIMA, Y ;

AKAKABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4237-4239

[22] BIOTRANSFORMATION OF AROMATIC KETONES WITH CELL-CULTURES OF CARROT, TOBACCO AND GARDENIA [J].

NAOSHIMA, Y ;

AKAKABE, Y .

PHYTOCHEMISTRY, 1991, 30 (11) :3595-3597

[23] NAD(P)+-NAD(P)H MODELS .59. 1,2-REDUCTION VERSUS 1,4-REDUCTION OF BETA,GAMMA-UNSATURATED ALPHA-KETO ESTER [J].

OHNO, A ;

YASUMA, T ;

NAKAMURA, K ;

OKA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (09) :2905-2906

[24] Syntheses and structure-activity relationships of taxoids derived from 14 beta-hydroxy-10-deacetylbaccatin III [J].

Ojima, I ;

Slater, JC ;

Kuduk, SD ;

Takeuchi, CS ;

Gimi, RH ;

Sun, CM ;

Park, YH ;

Pera, P ;

Veith, JM ;

Bernacki, RJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (03) :267-278

[25] Overview of the angiotensin-converting-enzyme inhibitors [J].

Piepho, RW .

AMERICAN JOURNAL OF HEALTH-SYSTEM PHARMACY, 2000, 57 (19) :S3-S7

[26] POLYFUNCTIONAL (R)-2-HYDROXYCARBOXYLIC ACIDS BY REDUCTION OF 2-OXO ACIDS WITH HYDROGEN GAS OR FORMATE AND RESTING CELLS OF PROTEUS-VULGARIS [J].

SCHUMMER, A ;

YU, H ;

SIMON, H .

TETRAHEDRON, 1991, 47 (43) :9019-9034

[27] SYNTHESIS AND STEREOCHEMISTRY OF ARYLIDENEPYRUVIC ACIDS AND DERIVED TRANS-ALPHA-BROMOCINNAMIC ACIDS [J].

STECHER, ED ;

INCORVIA, MJ ;

KERBEN, B ;

LAVINE, D ;

OEN, M ;

SUHL, E .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (26) :4453-4457

[28] BIOTRANSFORMATION OF EXOGENOUS SUBSTRATES BY PLANT-CELL CULTURES [J].

SUGA, T ;

HIRATA, T .

PHYTOCHEMISTRY, 1990, 29 (08) :2393-2406

[29] DIASTEREOSELECTIVE REDUCTION OF CHIRAL BETA,GAMMA-UNSATURATED ALPHA-OXO ESTERS - ASYMMETRIC-SYNTHESIS OF THE FATTY-ACID MOIETY OF SYMBIORAMIDE [J].

SUGIMURA, H ;

YOSHIDA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4484-4486

[30] LARGE-SCALE AND HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL C-13 SIDE-CHAIN THROUGH ASYMMETRIC DIHYDROXYLATION [J].

WANG, ZM ;

KOLB, HC ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :5104-5105

← 1 2 3 4 →