A Covalent Succinylcysteine-like Intermediate in the Enzyme-Catalyzed Transformation of Maleate to Fumarate by Maleate Isomerase

被引:33
作者
Fisch, Florian [1 ]
Fleites, Carlos Martinez [1 ]
Delenne, Marie [1 ]
Baudendistel, Nina [3 ]
Hauer, Bernhard [3 ]
Turkenburg, Johan P. [1 ]
Hart, Sam [1 ]
Bruce, Neil C. [2 ]
Grogan, Gideon [1 ]
机构
[1] Univ York, York Struct Biol Lab, Dept Chem, York YO10 5YW, N Yorkshire, England
[2] Univ York, Ctr Novel Agr Prod, Dept Biol, York YO10 5YW, N Yorkshire, England
[3] GVF E, BASF SE, Ludwigshafen, Germany
关键词
CIS-TRANS ISOMERASE; SUBTILIS GLUTAMATE RACEMASE; ARYLMALONATE DECARBOXYLASE; CRYSTAL-STRUCTURE; ESCHERICHIA-COLI; MECHANISM; EVOLUTION; CLONING; ACID;
D O I
10.1021/ja1053576
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Maleate isomerase (MI), a member of the Asp/Glu racemase superfamily, catalyzes cis-trans isomerization of the C2-C3 double bond in maleate to yield fumarate. Mutational studies, in conjunction with the structure of the C194A mutant of Nocardia farcinica MI cocrystallized with maleate, have revealed an unprecedented mode of catalysis for the superfamily in which the isomerization reaction is initiated by nucleophilic attack of cysteine at the double bond, yielding a covalent succinylcysteine-like intermediate.
引用
收藏
页码:11455 / 11457
页数:3
相关论文
共 22 条
[1]   S-(2-succinyl)cysteine:: A novel chemical modification of tissue proteins by a Krebs cycle intermediate [J].
Alderson, Nathan L. ;
Wang, Yuping ;
Blatnik, Matthew ;
Frizzell, Norma ;
Walla, Michael D. ;
Lyons, Timothy J. ;
Alt, Nadja ;
Carson, James A. ;
Nagai, Ryji ;
Thorpe, Suzanne R. ;
Baynes, John W. .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2006, 450 (01) :1-8
[2]   Pyrazolopyrimidinediones Are Selective Agents for Helicobacter pylori That Suppress Growth through Inhibition of Glutamate Racemase (MurI) [J].
de Jonge, B. L. M. ;
Kutschke, A. ;
Uria-Nickelsen, M. ;
Kamp, H. D. ;
Mills, S. D. .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2009, 53 (08) :3331-3336
[3]   CYTOSINE METHYLTRANSFERASE FROM ESCHERICHIA-COLI IN WHICH ACTIVE-SITE CYSTEINE IS REPLACED WITH SERINE IS PARTIALLY ACTIVE [J].
GABBARA, S ;
SHELUHO, D ;
BHAGWAT, AS .
BIOCHEMISTRY, 1995, 34 (27) :8914-8923
[4]   PURIFICATION, CLONING, AND COFACTOR INDEPENDENCE OF GLUTAMATE RACEMASE FROM LACTOBACILLUS [J].
GALLO, KA ;
KNOWLES, JR .
BIOCHEMISTRY, 1993, 32 (15) :3981-3990
[5]   Active site residues of glutamate racemase [J].
Glavas, S ;
Tanner, ME .
BIOCHEMISTRY, 2001, 40 (21) :6199-6204
[6]   Molecular analysis of maleate cis-trans isomerase from thermophilic bacteria [J].
Hatakeyama, K ;
Goto, M ;
Uchida, Y ;
Kobayashi, M ;
Terasawa, M ;
Yukawa, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (03) :569-576
[7]   Gene cloning and characterization of maleate cis-trans isomerase from Alcaligenes faecalis [J].
Hatakeyama, K ;
Asai, Y ;
Uchida, Y ;
Kobayashi, M ;
Terasawa, M ;
Yukawa, H .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1997, 239 (01) :74-79
[8]   Analysis of oxidation sensitivity of maleate cis-trans isomerase from Serratia marcescens [J].
Hatakeyama, K ;
Goto, M ;
Kobayashi, M ;
Terasawa, M ;
Yukawa, H .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (07) :1477-1485
[9]   Active-site mobility revealed by the crystal structure of arylmalonate decarboxylase from Bordetella bronchiseptica [J].
Kuettner, E. Bartholomeus ;
Keim, Antje ;
Kircher, Markus ;
Rosmus, Susann ;
Straeter, Norbert .
JOURNAL OF MOLECULAR BIOLOGY, 2008, 377 (02) :386-394
[10]   Structural insight into gene duplication, gene fusion and domain swapping in the evolution of PLP-independent amino acid racemases [J].
Liu, LJ ;
Iwata, K ;
Yohda, M ;
Miki, K .
FEBS LETTERS, 2002, 528 (1-3) :114-118