Biocatalytic resolution of 1,2-epoxyoctane using resting cells of different yeast strains with novel epoxide hydrolase activities

被引：41

作者：

Botes, AL

Weijers, CAGM

van Dyk, MS

机构：

[1] Univ Orange Free State, Dept Microbiol & Biochem, ZA-9300 Bloemfontein, South Africa

[2] Wageningen Univ Agr, Dept Food Technol & Nutr Sci, Div Ind Microbiol, NL-6700 EV Wageningen, Netherlands

来源：

BIOTECHNOLOGY LETTERS | 1998年 / 20卷 / 04期

关键词：

D O I：

10.1023/A:1005395817739

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：

Yeast strains (187) from 25 different genera were screened for the hydrolysis of 1,2-epoxyoctane. Epoxide hydrolase activity was found for 54 yeast strains. Asymmetric hydrolysis of 1,2-epoxyoctane was found for 8 yeast strains belonging to the genera Trichosporon, Rhodotorula, and Rhodosporidium. All these strains preferentially hydrolysed (R)-1,2-epxoyoctane to (R)-1,2-octanediol. Excellent enantioselectivity (E > 200) for 1,2-epopxyoctane is reported for the first time. Substrate concentration of 500 mM were used without any decrease in enzyme activity.

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页码：421 / 426

页数：6

相关论文

共 28 条

[1] Synthesis of enantiopure epoxides through biocatalytic approaches [J].

Archelas, A ;

Furstoss, R .

ANNUAL REVIEW OF MICROBIOLOGY, 1997, 51 :491-525

[2] Chemoenzymic resolution and deracemisation of (+/-)-1-methyl-1,2-epoxycyclohexane: The synthesis of(1-S,2-S)-1-methylcyclohexane-1,2-diol. [J].

Archer, IVJ ;

Leak, DJ ;

Widdowson, DA .

TETRAHEDRON LETTERS, 1996, 37 (48) :8819-8822

[3] SUBSTRATE ENANTIOSELECTION IN THE MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF MONOSUBSTITUTED OXIRANES - EFFECTS OF BRANCHING OF ALKYL CHAINS [J].

BELLUCCI, G ;

CHIAPPE, C ;

CONTI, L ;

MARIONI, F ;

PIERINI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5978-5983

[4]

BELLUCI G, 1995, J CHEM SOC P1, P361

[5] Novel aliphatic epoxide hydrolase activities from dematiaceous fungi [J].

Grogan, G ;

Roberts, SM ;

Willetts, AJ .

FEMS MICROBIOLOGY LETTERS, 1996, 141 (2-3) :239-243

[6] HIGH-YIELD PRODUCTION OF OPTICALLY-ACTIVE 1,2-DIOLS FROM THE CORRESPONDING RACEMATES BY MICROBIAL STEREOINVERSION [J].

HASEGAWA, J ;

OGURA, M ;

TSUDA, S ;

MAEMOTO, S ;

KUTSUKI, H ;

OHASHI, T .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (07) :1819-1827

[7] Enantioselective catalytic ring opening of epoxides with carboxylic acids [J].

Jacobsen, EN ;

Kakiuchi, F ;

Konsler, RG ;

Larrow, JF ;

Tokunaga, M .

TETRAHEDRON LETTERS, 1997, 38 (05) :773-776

[8]

KATSUKI T, 1995, J SYN ORG CHEM JPN, V53, P941

[9] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[10] Kinetic resolution of terminal epoxides via highly regioselective and enantioselective ring opening with TMSN(3). An efficient, catalytic route to 1,2-amino alcohols [J].

Larrow, JF ;

Schaus, SE ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) :7420-7421