POLYETHYLENE GLYCOL-MODIFIED LIPASE CATALYZES ASYMMETRIC ALCOHOLYSIS OF DELTA-DECALACTONE IN N-DECANOL

被引:10
作者
UEMURA, T
FURUKAWA, M
KODERA, Y
HIROTO, M
MATSUSHIMA, A
KUNO, H
MATSUSHITA, H
SAKURAI, K
INADA, Y
机构
[1] TOIN UNIV YOKOHAMA,TOIN HUMAN SCI & TECHNOL CTR,DEPT MAT SCI & TECHNOL,AOBA KU,YOKOHAMA,KANAGAWA 225,JAPAN
[2] JAPAN TOBACCO INC,LIFE SCI RES LAB,YOKOHAMA,KANAGAWA 227,JAPAN
关键词
D O I
10.1007/BF00134197
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Lipase from Pseudomonas cepacia was modified with 2,4-bis[O-methoxypoly(ethylene glycol)]-6-chloro-s-triazine(activated PEG(2)) to form PEG-lipase. The PEG-lipase, soluble and active in organic solvents, catalyzes asymmetric alcoholysis of racemic delta-decalactone in alcohols to form (R)-5-hydroxydecanoic acid alkyl esters. The yield was 69% with 83% enantiomeric excess after 3 hr-reaction in n-decanol at 50 degrees C. The advantage of this reaction is that the alcoholysis proceeds efficiently in straight hydrophobic substrates without any organic solvents.
引用
收藏
页码:61 / 66
页数:6
相关论文
共 12 条
[1]   POLYMERIZATION OF 10-HYDROXYDECANOIC ACID IN BENZENE WITH POLYETHYLENE GLYCOL-MODIFIED LIPASE [J].
AJIMA, A ;
YOSHIMOTO, T ;
TAKAHASHI, K ;
TAMAURA, Y ;
SAITO, Y ;
INADA, Y .
BIOTECHNOLOGY LETTERS, 1985, 7 (05) :303-306
[2]   ENZYMATIC RESOLUTION OF RACEMIC LACTONES [J].
BLANCO, L ;
GUIBEJAMPEL, E ;
ROUSSEAU, G .
TETRAHEDRON LETTERS, 1988, 29 (16) :1915-1918
[3]   ALCOHOLYSIS OF EPSILON-DECALACTONE WITH POLYETHYLENE GLYCOL-MODIFIED LIPASE IN 1,1,1-TRICHLOROETHANE [J].
FURUKAWA, M ;
KODERA, Y ;
UEMURA, T ;
HIROTO, M ;
MATSUSHIMA, A ;
KUNO, H ;
MATSUSHITA, H ;
INADA, Y .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1994, 199 (01) :41-45
[4]   LIPASE-CATALYZED PREPARATION OF OPTICALLY-ACTIVE GAMMA-BUTYROLACTONES IN ORGANIC-SOLVENTS [J].
GUTMAN, AL ;
ZUOBI, K ;
BRAVDO, T .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3546-3552
[5]   DETERMINATION OF FREE AMINO GROUPS IN PROTEINS BY TRINITROBENZENESULFONIC ACID [J].
HABEEB, AFS .
ANALYTICAL BIOCHEMISTRY, 1966, 14 (03) :328-&
[6]   ESTER SYNTHESIS CATALYZED BY POLYETHYLENE GLYCOL-MODIFIED LIPASE IN BENZENE [J].
INADA, Y ;
NISHIMURA, H ;
TAKAHASHI, K ;
YOSHIMOTO, T ;
SAHA, AR ;
SAITO, Y .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 122 (02) :845-850
[7]  
KIKKAWA S, 1989, BIOCHEM INT, V19, P1125
[8]   LACTONE SYNTHESIS FROM 16-HYDROXYHEXADECANOIC ACID ETHYL-ESTER IN ORGANIC-SOLVENTS CATALYZED WITH POLYETHYLENE GLYCOL-MODIFIED LIPASE [J].
KODERA, Y ;
FURUKAWA, M ;
YOKOI, M ;
KUNO, H ;
MATSUSHITA, H ;
INADA, Y .
JOURNAL OF BIOTECHNOLOGY, 1993, 31 (02) :219-224
[9]  
ONO K, 1991, Journal of Biomaterials Science Polymer Edition, V2, P61, DOI 10.1163/156856291X00061
[10]   A CHEMICAL MODIFICATION TO MAKE HORSERADISH-PEROXIDASE SOLUBLE AND ACTIVE IN BENZENE [J].
TAKAHASHI, K ;
NISHIMURA, H ;
YOSHIMOTO, T ;
SAITO, Y ;
INADA, Y .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 121 (01) :261-265