MICROBIAL STEREO-DIFFERENTIATING REDUCTION OF THE CARBONYL GROUPS LOCATED ON THE C2 AXES OF GYROCHIRAL MOLECULES

被引:30
作者
NAKAZAKI, M
CHIKAMATSU, H
NAEMURA, K
NISHINO, M
MURAKAMI, H
ASAO, M
机构
[1] Department of Chemistry, Faculty of Engineering Science, Osaka University, Toyonaka
关键词
D O I
10.1021/jo00393a028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantiomer selectivity of Curvularia lunata and Rhodotorula rubra with respect to some C2 ketone substrates having the C2 axis coincident with the carbonyl axis was examined. Both microbes exhibited a marked stereodifferentiation between enantiomers of (.+-.)-9-twist-brendanone, (.+-.)-2-brexanone, (.+-.)-D3-trishomocubanone (8), (.+-.)-bisnoradamantanone, (.+-.)-biphenyl, and (.+-.)-.alpha.-binaphthyl bridged ketones, selectively reducing the P-C2 ketone enantiomers.
引用
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页码:4588 / 4593
页数:6
相关论文
共 33 条
[1]  
BENTLEY R, 1970, MOL ASYMMETRY BIOL, V2, P41
[2]   SPECIFICATION OF MOLECULAR CHIRALITY [J].
CAHN, RS ;
INGOLD, C ;
PRELOG, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) :385-&
[3]   RESOLUTION OF TRISHOMOCUBANONE - ENANTIOMERIC (D3)-TRISHOMOCUBANES [J].
EATON, PE ;
LEIPZIG, B .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2483-2484
[4]   TRISHOMOCUBANONE (PENTACYCLO[6,3,0,0,2,6,03,10,05,9]UNDECAN-4-ONE) [J].
EATON, PE ;
HUDSON, RA ;
GIORDANO, C .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (23) :978-978
[5]   SYNTHESIS AND ABSOLUTE-CONFIGURATION OF ENANTIOMERICALLY PURE D3-TRISHOMOCUBANES (PENTACYCLO[6.3.0.02,6.03,10.05,9]UNDECANE) AND TRISHOMOCUBANONES [J].
HELMCHEN, G ;
STAIGER, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (02) :116-117
[6]   STEREOSELECTIVE HORSE LIVER ALCOHOL-DEHYDROGENASE CATALYZED OXIDO-REDUCTIONS OF SOME BICYCLIC [2.2.1] AND [3.2.1] KETONES AND ALCOHOLS [J].
IRWIN, AJ ;
JONES, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (26) :8476-8482
[7]  
JONES JB, 1976, APPLICATIONS BIOCH 1, pCH4
[8]  
KIESLICH K, 1969, SYNTHESIS-STUTTGART, V1, P120
[9]  
KIESLICH K, 1969, SYNTHESIS-STUTTGART, V1, P147
[10]  
Krow G., 1970, TOP STEREOCHEM, V5, P31