Biocatalysis in organic synthesis: The use of nitrile- and amide-hydrolyzing microorganisms

被引:127
作者
Sugai, T
Yamazaki, T
Yokoyama, M
Ohta, H
机构
[1] Department of Chemistry, Keio University, Yokohama, 223
关键词
nitrile; amide; hydrolysis; microorganisms; organic synthesis;
D O I
10.1271/bbb.61.1419
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
This review covers recent examples of synthetic transformation of nitriles and amides by microbial enzyme systems. A variety of substrates and products involving enantiomerically enriched forms of chiral substances are referred to. The stereochemical course of enzyme-catalyzed hydrolysis is briefly commented on. Special emphasis is placed upon the range of functional groups that are acceptable by enzymes and/or survive under the transformation, as well as the advantages as a synthetic tool for conversion under mild conditions.
引用
收藏
页码:1419 / 1427
页数:9
相关论文
共 100 条
[31]   ASYMMETRIC HYDROLYSIS OF CHIRAL NITRILES BY RHODOCOCCUS-RHODOCHROUS NCIMB-11216 NITRILASE [J].
GRADLEY, ML ;
KNOWLES, CJ .
BIOTECHNOLOGY LETTERS, 1994, 16 (01) :41-46
[32]   Conversion of a cyanhydrin compound into S-(-)-3-phenyllactic acid by enantioselective hydrolytic activity of Pseudomonas sp BC-18 [J].
Hashimoto, Y ;
Kobayashi, E ;
Endo, T ;
Nishiyama, M ;
Horinouchi, S .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1996, 60 (08) :1279-1283
[33]   PURIFICATION AND CHARACTERIZATION OF AN L-AMINO AMIDASE FROM MYCOBACTERIUM-NEOAURUM ATCC-25795 [J].
HERMES, HFM ;
TANDLER, RF ;
SONKE, T ;
DIJKHUIZEN, L ;
MEIJER, EM .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1994, 60 (01) :153-159
[34]   ENZYMATIC-HYDROLYSIS OF NITRILES AND DINITRILES [J].
HONICKESCHMIDT, P ;
SCHNEIDER, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (08) :648-650
[35]  
Inagaki K, 1997, SYNLETT, P119
[36]  
JOERES U, 1994, APPL MICROBIOL BIOT, V40, P599
[37]  
JOERES U, 1994, APPL MICROBIOL BIOT, V40, P606
[38]   MICROBIAL HYDROLYSIS OF 3-SUBSTITUTED GLUTARONITRILES [J].
KAKEYA, H ;
SAKAI, N ;
SANO, A ;
YOKOYAMA, M ;
SUGAI, T ;
OHTA, H .
CHEMISTRY LETTERS, 1991, (10) :1823-1824
[39]   MICROBIAL HYDROLYSIS AS A POTENT METHOD FOR THE PREPARATION OF OPTICALLY-ACTIVE NITRILES, AMIDES AND CARBOXYLIC-ACIDS [J].
KAKEYA, H ;
SAKAI, N ;
SUGAI, T ;
OHTA, H .
TETRAHEDRON LETTERS, 1991, 32 (10) :1343-1346
[40]   PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS BY USING ENZYMES .11. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY ACID-DERIVATIVES BY MICROBIAL HYDROLYSIS OF CYANOHYDRINS AND ITS APPLICATION TO THE SYNTHESIS OF (R)-4-DODECANOLIDE [J].
KAKEYA, H ;
SAKAI, N ;
SUGAI, T ;
OHTA, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (07) :1877-1881