STEREODIRECTING SUBSTITUENT EFFECTS DURING ENZYME-CATALYZED SYNTHESIS OF CIS-DIHYDRODIOL METABOLITES OF 1,4-DISUBSTITUTED BENZENE SUBSTRATES

被引：49

作者：

BOYD, DR

SHARMA, ND

HAND, MV

GROOCOCK, MR

KERLEY, NA

DALTON, H

CHIMA, J

SHELDRAKE, GN

机构：

[1] UNIV WARWICK,DEPT BIOL SCI,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

[2] ZENECA SPECIALT,MANCHESTER M9 3DA,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 11期

关键词：

D O I：

10.1039/c39930000974

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The cis-dihydrodiol enantiomer preferentially formed, by dioxygenase-catalysed oxidation of 1,4-disubstituted benzene substrates in growing cultures of Pseudomonas putida UV4, is found to be largely controlled by the relative size of the substituents.

引用

收藏

页码：974 / 976

页数：3

相关论文

共 11 条

[1] ENANTIOMERIC EXCESS AND ABSOLUTE-CONFIGURATION DETERMINATION OF CIS-DIHYDRODIOLS FROM BACTERIAL METABOLISM OF MONOCYCLIC ARENES [J].

BOYD, DR ;

DORRITY, MRJ ;

HAND, MV ;

MALONE, JF ;

SHARMA, ND ;

DALTON, H ;

GRAY, DJ ;

SHELDRAKE, GN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :666-667

[2] ENZYMATIC AND CHEMICAL SYNTHESES OF CIS-DIHYDRODIOL DERIVATIVES OF MONOCYCLIC ARENES [J].

BOYD, DR ;

HAND, MV ;

SHARMA, ND ;

CHIMA, J ;

DALTON, H ;

SHELDRAKE, GN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (22) :1630-1632

[3]

BOYD DR, UNPUB

[4] STEREOSPECIFIC HYDROXYLATION OF INDAN BY ESCHERICHIA-COLI CONTAINING THE CLONED TOLUENE DIOXYGENASE GENES FROM PSEUDOMONAS-PUTIDA F1 [J].

BRAND, JM ;

CRUDEN, DL ;

ZYLSTRA, GJ ;

GIBSON, DT .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1992, 58 (10) :3407-3409

[5] THE USE OF CYCLOHEXA-3,5-DIENE-1,2-DIOLS IN ENANTIOSPECIFIC SYNTHESIS [J].

CARLESS, HAJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :795-826

[6]

GIBSON DT, 1984, MICROBIAL DEGRADATIO, P181, DOI DOI 10.1002/ACTP.1986.010371127

[7] PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES TO THE FREE CIS-DIOL METABOLITE PRODUCED FROM THE OXIDATION OF BROMOBENZENE BY PSEUDOMONAS-PUTIDA - SYNTHESIS OF NEW HOMOCHIRAL 3-ALKYNYL CIS-CYCLOHEXA-3,5-DIENE-1,2-DIOLS [J].

HUDLICKY, T ;

BOROS, EE .

TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :217-220

[8]

ISAACS NS, 1987, PHYSICAL ORGANIC CHE, P298

[9]

LEVY SV, 1991, SYNLETT, P741

[10]

SHELDRAKE GN, 1992, CHIRALITY IND COMMER, pCH6