ArticleJournal of the American Chemical Society2012
Reaction of cis-3-chloroacrylic acid dehalogenase with an allene substrate, 2,3-butadienoate: hydration via an enamine.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 20 citations in OpenAlex.
- Kinetic and Structural Analysis of Two Linkers in the Tautomerase Superfamily: Analysis and Implications.Biochemistry · 2021Article
- Kinetic and structural characterization of a cis-3-Chloroacrylic acid dehalogenase homologue in Pseudomonas sp. UW4: A potential step between subgroups in the tautomerase superfamily.Archives of biochemistry and biophysics · 2017Article
- Resolution of the uncertainty in the kinetic mechanism for the trans-3-Chloroacrylic acid dehalogenase-catalyzed reaction.Archives of biochemistry and biophysics · 2017Article
- Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse.Chemical reviews · 2017Review
- Inhibition of Inosine-5'-monophosphate Dehydrogenase from Bacillus anthracis: Mechanism Revealed by Pre-Steady-State Kinetics.Biochemistry · 2016Article
- Stereochemical Consequences of Vinylpyruvate Hydratase-Catalyzed Reactions.Biochemistry · 2016Article
- Substrate protein folds while it is bound to the ATP-independent chaperone Spy.Nature structural & molecular biology · 2016Article
- Reactions of Cg10062, a cis-3-Chloroacrylic Acid Dehalogenase Homologue, with Acetylene and Allene Substrates: Evidence for a Hydration-Dependent Decarboxylation.Biochemistry · 2015Article
- A century of enzyme kinetic analysis, 1913 to 2013.FEBS letters · 2013Review
- A mutational analysis of the active site loop residues in cis-3-Chloroacrylic acid dehalogenase.Biochemistry · 2013Article
- A pre-steady state kinetic analysis of the αY60W mutant of trans-3-chloroacrylic acid dehalogenase: implications for the mechanism of the wild-type enzyme.Biochemistry · 2012Article
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
cis-3-Chloroacrylic acid dehalogenase (cis-CaaD) catalyzes the hydrolytic dehalogenation of cis-3-haloacrylates to yield malonate semialdehyde. The enzyme processes other substrates including an allene (2,3-butadienoate) to produce acetoacetate. In the course of a stereochemical analysis of the cis-CaaD-catalyzed reaction using this allene, the enzyme was unexpectedly inactivated in the presence of NaBH(4) by the reduction of a covalent enzyme-substrate bond. Covalent modification was surprising because the accumulated evidence for cis-CaaD dehalogenation favored a mechanism involving direct substrate hydration mediated by Pro-1. However, the results of subsequent mechanistic, pre-steady state and full progress kinetic experiments are consistent with a mechanism in which an enamine forms between Pro-1 and the allene. Hydrolysis of the enamine or an imine tautomer produces acetoacetate. Reduction of the imine species is likely responsible for the observed enzyme inactivation. This is the first reported observation of a tautomerase superfamily member functioning by covalent catalysis. The results may suggest that some fraction of the cis-CaaD-catalyzed dehalogenation of cis-3-haloacrylates also proceeds by covalent catalysis.
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