New structural and chemical insight into the catalytic mechanism of epoxide hydrolases

被引:36
作者
Armstrong, RN
Cassidy, CS
机构
[1] Vanderbilt Univ, Sch Med, Dept Biochem, Nashville, TN 37232 USA
[2] Vanderbilt Univ, Sch Med, Dept Chem, Nashville, TN 37232 USA
[3] Vanderbilt Univ, Sch Med, Ctr Mol Toxicol, Nashville, TN 37232 USA
关键词
hydrolysis; epoxide; covalent intermediate; electrophilic catalysis;
D O I
10.1081/DMR-100102337
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
New structural and mechanistic data on epoxide hydrolases provide additional insight into the details of how these enzymes function. The data reveal that, in addition to the catalytic triad located in the core domain that carries out the hydrolytic reaction, there are two tyrosine residues, located in the cap domain, which assist in the initial alkylation event.
引用
收藏
页码:327 / 338
页数:12
相关论文
共 32 条
[1]   Catalytic triad of microsomal epoxide hydrolase:: replacement of Glu404 with Asp leads to a strongly increased turnover rate [J].
Arand, M ;
Müller, F ;
Mecky, A ;
Hinz, W ;
Urban, P ;
Pompon, D ;
Kellner, R ;
Oesch, F .
BIOCHEMICAL JOURNAL, 1999, 337 :37-43
[2]   Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase [J].
Arand, M ;
Hemmer, H ;
Dürk, H ;
Baratti, J ;
Archelas, A ;
Furstoss, R ;
Oesch, F .
BIOCHEMICAL JOURNAL, 1999, 344 :273-280
[3]   SEQUENCE SIMILARITY OF MAMMALIAN EPOXIDE HYDROLASES TO THE BACTERIAL HALOALKANE DEHALOGENASE AND OTHER RELATED PROTEINS - IMPLICATION FOR THE POTENTIAL CATALYTIC MECHANISM OF ENZYMATIC EPOXIDE HYDROLYSIS [J].
ARAND, M ;
GRANT, DF ;
BEETHAM, JK ;
FRIEDBERG, T ;
OESCH, F ;
HAMMOCK, BD .
FEBS LETTERS, 1994, 338 (03) :251-256
[4]  
Arand M, 1996, J BIOL CHEM, V271, P4223
[5]   Detoxification of environmental mutagens and carcinogens: Structure, mechanism, and evolution of liver epoxide hydrolase [J].
Argiriadi, MA ;
Morisseau, C ;
Hammock, BD ;
Christianson, DW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (19) :10637-10642
[6]  
Armstrong P, 1999, EXA, V9, P51
[7]   Kinetic and chemical mechanism of epoxide hydrolase [J].
Armstrong, RN .
DRUG METABOLISM REVIEWS, 1999, 31 (01) :71-86
[8]   ENZYME-CATALYZED DETOXICATION REACTIONS - MECHANISMS AND STEREOCHEMISTRY [J].
ARMSTRONG, RN .
CRC CRITICAL REVIEWS IN BIOCHEMISTRY, 1987, 22 (01) :39-88
[9]   GENE EVOLUTION OF EPOXIDE HYDROLASES AND RECOMMENDED NOMENCLATURE [J].
BEETHAM, JK ;
GRANT, D ;
ARAND, M ;
GARBARINO, J ;
KIYOSUE, T ;
PINOT, F ;
OESCH, F ;
BELKNAP, WR ;
SHINOZAKI, K ;
HAMMOCK, BD .
DNA AND CELL BIOLOGY, 1995, 14 (01) :61-71
[10]  
BLOMSTER M, 1995, EUR J BIOCHEM, V231, P528, DOI 10.1111/j.1432-1033.1995.tb20728.x