Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: Kinetic analysis of His263 and Ser110 site-directed mutants

Journal of Molecular Biology

Volumn 346, Issue 1, 2005, Pages 241-251

  Li, Chen ^a   Montgomery, Mark G ^b   Mohammed, Fiyaz ^b   Li, Jian Jun ^a   Wood, Stephen P ^b   Bugg, Timothy D H ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

C C hydrolase; general base mechanism; serine catalytic triad; hydrolase

Indexed keywords

HISTIDINE; HYDROLASE; SERINE; SERINE DEHYDRATASE; WATER;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME KINETICS; ENZYME MECHANISM; ENZYME STABILITY; ENZYME SUBSTRATE; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN FOLDING; SITE DIRECTED MUTAGENESIS; STEADY STATE; ULTRAVIOLET SPECTROSCOPY;

ESCHERICHIA COLI;

EID: 12344275671     PISSN: 00222836     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmb.2004.11.032     Document Type: Article

References (19)

1. T.D.H. Bugg, and C.J. Winfield Enzymatic cleavage of aromatic rings: mechanistic aspects of the catechol dioxygenases and later enzymes of bacterial oxidative cleavage pathways Nature Prod. Rep. 15 1998 513 530
2. E. Diaz, and K.N. Timmis Identification of functional residues in a 2-hydroxymuconic semi-aldehyde hydrolase: a new member of the α/β hydrolase-fold family of enzymes which cleaves carbon-carbon-bonds J. Biol. Chem. 270 1995 6403 6411
3. W.W.Y. Lam, and T.D.H. Bugg Chemistry of extradiol aromatic ring cleavage: isolation of a stable dienol ring fission intermediate and stereochemistry of its enzymatic hydrolytic cleavage J. Chem. Soc. Chem. Commun. 1994 1163 1164
4. W.W.Y. Lam, and T.D.H. Bugg Purification, characterisation and stereochemical analysis of a C-C hydrolase: 2-hydroxy-6-keto-nona-2,4-diene 1,9-dioic acid 5,6-hydrolase Biochemistry 36 1997 12242 12251
5. I.M.J. Henderson, and T.D.H. Bugg Pre-steady state kinetic analysis of 2-hydroxy-6-keto-nona-2,4-diene 1,9-dioic acid 5,6-hydrolase: kinetic evidence for enol/keto tautomerisation Biochemistry 36 1997 12252 12258
6. S.M. Fleming, T.A. Robertson, G.J. Langley, and T.D.H. Bugg Catalytic mechanism of a C-C hydrolase enzyme: evidence for a gem-diol intermediate, not an acyl enzyme Biochemistry 39 2000 1522 1531
7. N. Nandhagopal, A. Yamada, T. Hatta, E. Masai, M. Fukuda, Y. Mitsui, and T. Senda Crystal structure of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (HPDA) hydrolase (BphD enzyme) from the Rhodococcus sp. strain RHA1 of the PCB degradation pathway J. Mol. Biol. 309 2001 1139 1151
8. S.Y.K. Seah, G. Terracina, J.T. Bolin, P. Riebel, V. Snieckus, and L.D. Eltis Purification and preliminary characterisation of a serine hydrolase involved in the microbial degradation of polychlorinated biphenyls J. Biol. Chem. 273 1998 22943 22949
9. D.M. Speare, S.M. Fleming, M.N. Beckett, J.J. Li, and T.D.H. Bugg Synthetic 6-aryl 2-hydroxy-6-keto-hexa-2,4-dienoic acid substrates for C-C hydrolase BphD: investigation of a general base catalytic mechanism Org. Biomol. Chem. 2 2004 2942 2950
10. G. Dunn, M.G. Montgomery, F. Mohammed, A. Coker, J.B. Cooper, and T. Robertson The structure of the C-C bond hydrolase MhpC provides insights into its catalytic mechanism J. Mol. Biol. 2005 (this issue)
11. J.R. Pollard, I.M.J. Henderson, and T.D.H. Bugg Chemical and biochemical properties of 2-hydroxypentadienoic acid, a homologue of enolpyruvic acid J. Chem. Soc. Chem. Commun. 1997 1885 1886
12. P. Carter, and J.A. Wells Dissecting the catalytic triad of a serine protease Nature 332 1988 564 568
13. + and substituted benzyl alcohols Biochemistry 33 1994 5230 5237
14. Y. Liu, J.B. Thoden, J. Kim, E. Berger, A.M. Gulick, and F.J. Ruzicka Mechanistic roles of tyrosine-149 and serine-124 in UDP-galactose 4-epimerase from Escherichia coli Biochemistry 36 1997 10675 10684
15. S. Nakagawa, H.A. Yu, M. Karplus, and H. Umeyama Active site dynamics of acyl-chymotrypsin Proteins: Struct. Funct. Genet. 16 1993 172 194
16. D.J. Tantillo, and K.N. Houk Canonical binding arrays as molecular recognition elements in the immune system: tetrahedral anions and the ester hydrolysis transition state Chem. Biol. 8 2001 535 545
17. E.R. Blakley, and F.J. Simpson The microbial metabolism of cinnamic acid Can. J. Microbiol. 10 1963 175 185
18. Sambrook, J., Fritsch, E. F. & Maniatis, T. (1989). Molecular Cloning: A Laboratory Manual. 2nd edit. p. 1.74, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
19. M.M. Bradford A rapid and sensitive for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248 254