CHEMOENZYMATIC PREPARATION OF ATROLACTIC AND MOSHERS ACID USING ASPERGILLUS-ORYZAE PROTEASE

被引：22

作者：

FEICHTER, C

FABER, K

GRIENGL, H

机构：

[1] Christian Doppler Laboratory for Chiral Compounds, Institute of Organic Chemistry, Graz University of Technology, A-8010 Graz

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 03期

关键词：

D O I：

10.1039/p19910000653

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sterically demanding alpha-methyl- and alpha-trifluoromethyl-mandelic esters 5a and 6a were conveniently resolved on a large scale by a protease from Aspergillus oryzae leading to both enantiomers of atrolactic acid 5b and a precursor of Mosher's acid 6b in 75-88% e.e. Single recrystallisation led to optically pure material.

引用

页码：653 / 654

页数：2

共 21 条

[1] ENZYME CATALYZED-HYDROLYSIS OF DIALKYLATED PROPANEDIOIC ACID DIESTERS, CHAIN-LENGTH DEPENDENT REVERSAL OF ENANTIOSELECTIVITY [J].

BJORKLING, F ;

BOUTELJE, J ;

GATENBECK, S ;

HULT, K ;

NORIN, T ;

SZMULIK, P .

TETRAHEDRON, 1985, 41 (07) :1347-1352

[2]

BJORKLING F, 1987, BIOCATALYSIS, V1, P83

[3] THE STEREOCHEMISTRY OF RANEY NICKEL ACTION .3. THE STEREOCHEMICAL COURSE OF DEHYDROXYLATIONS IN THE BENZYL ALCOHOL SERIES [J].

BONNER, WA ;

ZDERIC, JA ;

CASALETTO, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (20) :5086-5088

[4] NEW SYNTHETIC CARRIERS FOR ENZYMES [J].

BURG, K ;

MAUZ, O ;

NOETZEL, S ;

SAUBER, K .

ANGEWANDTE MAKROMOLEKULARE CHEMIE, 1988, 157 :105-121

[5] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[6] KINETIC RESOLUTION OF UNNATURAL AND RARELY OCCURRING AMINO-ACIDS - ENANTIOSELECTIVE HYDROLYSIS OF N-ACYL AMINO-ACIDS CATALYZED BY ACYLASE-I [J].

CHENAULT, HK ;

DAHMER, J ;

WHITESIDES, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6354-6364

[7]

CROUT DHG, 1989, MOD SYN MET, V5, P1

[8] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[9]

DAVIS HG, 1989, BIOTRANSFORMATIONS P, P25

[10] ENZYMES IN ORGANIC-SYNTHESIS .6. SCOPE AND ENANTIOSELECTIVITY OF ENZYMATIC HYDROLYSES OF ORGANOSILYL-SUBSTITUTED ESTERS [J].

DEJESO, B ;

BELAIR, N ;

DELEUZE, H ;

RASCLE, MC ;

MAILLARD, B .

TETRAHEDRON LETTERS, 1990, 31 (05) :653-654

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