ENZYMES IN ORGANIC-SYNTHESIS - OXIDOREDUCTIONS

被引:53
作者
FANG, JM [1 ]
LIN, CH [1 ]
BRADSHAW, CW [1 ]
WONG, CH [1 ]
机构
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 08期
关键词
D O I
10.1039/p19950000967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This article reviews the use of several oxidoreduction enzymes, including monooxygenases, chloroperoxidase, arene dioxygenase, lipoxygenase, galactose oxidase and alcohol dehydrogenases, in the preparation of optically pure or enriched epoxides, halohydrins, sulfoxides, hydroperoxides, alcohols, cyclohexadienediols, lactones and alpha-hydroxy aldehydes. The mechanisms of some of these enzyme-catalysed transformations, and their scopes and limitations in synthetic chemistry are also discussed. Representative syntheses of a key intermediate of 5-lipoxygenase inhibitor, a seven-carbon C-glycoside and an active component of the antibiotic bialaphos have been experimentally illustrated using Lactobacillus alcohol dehydrogenase, chloroperoxidase and glutamate dehydrogenase, respectively.
引用
收藏
页码:967 / 978
页数:12
相关论文
共 159 条
[101]   STEREOSPECIFIC OXIDATION OF ALIPHATIC-ALCOHOLS CATALYZED BY GALACTOSE-OXIDASE [J].
KLIBANOV, AM ;
ALBERTI, BN ;
MARLETTA, MA .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1982, 108 (02) :804-808
[102]   KINETIC MECHANISM OF THE CU(II) ENZYME GALACTOSE-OXIDASE [J].
KWIATKOWSKI, LD ;
ADELMAN, M ;
PENNELLY, R ;
KOSMAN, DJ .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1981, 14 (03) :209-222
[103]   ENZYMATIC CONVERSIONS OF 10,10-DIFLUOROARACHIDONIC ACID WITH PGH SYNTHASE AND SOYBEAN LIPOXYGENASE [J].
KWOK, PY ;
MUELLNER, FW ;
FRIED, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (12) :3692-3698
[104]   IMMOBILIZED LIPOXYGENASE IN CONTINUOUS PRODUCTION OF FATTY-ACID HYDROPEROXIDES [J].
LAAKSO, S .
LIPIDS, 1982, 17 (10) :667-671
[105]   RETENTION OF CONFIGURATION IN OXIDATION OF A CHIRAL BORONIC ACID BY THE FLAVOENZYME CYCLOHEXANONE OXYGENASE [J].
LATHAM, JA ;
WALSH, C .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (07) :527-528
[106]  
LEASON M, 1982, PHYTOCHEMISTRY, V21, P855, DOI 10.1016/0031-9422(82)80079-4
[107]  
LEY SV, 1990, SYNLETT, P393
[108]   MICROBIAL OXIDATION IN SYNTHESIS - A 6 STEP PREPARATION OF (+/-)-PINITOL FROM BENZENE [J].
LEY, SV ;
STERNFELD, F ;
TAYLOR, S .
TETRAHEDRON LETTERS, 1987, 28 (02) :225-226
[109]  
LIBBY RD, 1982, J BIOL CHEM, V257, P5030
[110]   STUDIES ON THE CHIRALITY OF SULFOXIDATION CATALYZED BY BACTERIAL FLAVOENZYME CYCLOHEXANONE MONO-OXYGENASE AND HOG LIVER FLAVIN ADENINE-DINUCLEOTIDE CONTAINING MONO-OXYGENASE [J].
LIGHT, DR ;
WAXMAN, DJ ;
WALSH, C .
BIOCHEMISTRY, 1982, 21 (10) :2490-2498