Literature DB >> 19725565

Reaction mechanism of cis-3-chloroacrylic acid dehalogenase: a theoretical study.

Robin Sevastik1, Christian P Whitman, Fahmi Himo.   

Abstract

The reaction mechanism of cis-3-chloroacrylic acid dehalogenase (cis-CaaD) is studied using the B3LYP density functional theory method. This enzyme catalyzes the hydrolytic dehalogenation of cis-3-chloroacrylic acid to yield malonate semialdehyde and HCl. The uncatalyzed reaction is first considered, and excellent agreement is found between the calculated barrier and the measured rate constant. The enzymatic reaction is then studied with an active site model consisting of 159 atoms. The results suggest an alternative mechanism for cis-CaaD catalysis and different roles for some active site residues in this mechanism.

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Year:  2009        PMID： 19725565      PMCID： PMC2798121          DOI： 10.1021/bi900879a

Source DB:  PubMed          Journal:  Biochemistry        ISSN： 0006-2960            Impact factor:   3.162


  30 in total

1.  Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model.

Authors:  Maurizio Cossi; Nadia Rega; Giovanni Scalmani; Vincenzo Barone
Journal:  J Comput Chem       Date:  2003-04-30       Impact factor: 3.376

Review 2.  Quantum chemical studies of radical-containing enzymes.

Authors:  Fahmi Himo; Per E M Siegbahn
Journal:  Chem Rev       Date:  2003-06       Impact factor: 60.622

3.  trans-3-Chloroacrylic acid dehalogenase from Pseudomonas pavonaceae 170 shares structural and mechanistic similarities with 4-oxalocrotonate tautomerase.

Authors:  G J Poelarends; R Saunier; D B Janssen
Journal:  J Bacteriol       Date:  2001-07       Impact factor: 3.490

Review 4.  Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes.

Authors:  Gerrit J Poelarends; Christian P Whitman
Journal:  Bioorg Chem       Date:  2004-10       Impact factor: 5.275

5.  Cloning, expression, and characterization of a cis-3-chloroacrylic acid dehalogenase: insights into the mechanistic, structural, and evolutionary relationship between isomer-specific 3-chloroacrylic acid dehalogenases.

Authors:  Gerrit J Poelarends; Hector Serrano; Maria D Person; William H Johnson; Alexey G Murzin; Christian P Whitman
Journal:  Biochemistry       Date:  2004-01-27       Impact factor: 3.162

6.  Reactions of trans-3-chloroacrylic acid dehalogenase with acetylene substrates: consequences of and evidence for a hydration reaction.

Authors:  Susan C Wang; Maria D Person; William H Johnson; Christian P Whitman
Journal:  Biochemistry       Date:  2003-07-29       Impact factor: 3.162

7.  Stereospecific alkylation of cis-3-chloroacrylic acid dehalogenase by (R)-oxirane-2-carboxylate: analysis and mechanistic implications.

Authors:  Gerrit J Poelarends; Hector Serrano; William H Johnson; Christian P Whitman
Journal:  Biochemistry       Date:  2004-06-08       Impact factor: 3.162

Review 8.  The 4-oxalocrotonate tautomerase family of enzymes: how nature makes new enzymes using a beta-alpha-beta structural motif.

Authors:  Christian P Whitman
Journal:  Arch Biochem Biophys       Date:  2002-06-01       Impact factor: 4.013

9.  The X-ray structure of trans-3-chloroacrylic acid dehalogenase reveals a novel hydration mechanism in the tautomerase superfamily.

Authors:  René M de Jong; Wim Brugman; Gerrit J Poelarends; Christian P Whitman; Bauke W Dijkstra
Journal:  J Biol Chem       Date:  2003-12-29       Impact factor: 5.157

10.  The roles of active-site residues in the catalytic mechanism of trans-3-chloroacrylic acid dehalogenase: a kinetic, NMR, and mutational analysis.

Authors:  Hugo F Azurmendi; Susan C Wang; Michael A Massiah; Gerrit J Poelarends; Christian P Whitman; Albert S Mildvan
Journal:  Biochemistry       Date:  2004-04-13       Impact factor: 3.162
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  2 in total

1.  Reactions of Cg10062, a cis-3-Chloroacrylic Acid Dehalogenase Homologue, with Acetylene and Allene Substrates: Evidence for a Hydration-Dependent Decarboxylation.

Authors:  Jamison P Huddleston; William H Johnson; Gottfried K Schroeder; Christian P Whitman
Journal:  Biochemistry       Date:  2015-05-01       Impact factor: 3.162

Review 2.  Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse.

Authors:  Vinayak Agarwal; Zachary D Miles; Jaclyn M Winter; Alessandra S Eustáquio; Abrahim A El Gamal; Bradley S Moore
Journal:  Chem Rev       Date:  2017-01-20       Impact factor: 60.622
  2 in total

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