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

Bioorganic Chemistry
Gerrit J Poelarends, C P Whitman

Abstract

The use of the soil fumigant Telone II, which contains a mixture of cis- and trans-1,3-dichloropropene, to control plant-parasitic nematodes is a common agricultural practice for maximizing yields of various crops. The effectiveness of Telone II is limited by the rapid turnover of the dichloropropenes in the soil due to the presence of bacterial catabolic pathways, which may be of recent origin. The characterization of three enzymes in these pathways, trans-3-chloroacrylic acid dehalogenase (CaaD), cis-3-chloroacrylic acid dehalogenase (cis-CaaD), and malonate semialdehyde decarboxylase (MSAD), has uncovered intriguing catalytic mechanisms as well as a fascinating evolutionary lineage for these proteins. Sequence comparisons and mutagenesis studies revealed that all three enzymes belong to the tautomerase superfamily. Tautomerase superfamily members with known structures are characterized by a beta-alpha-beta structural fold. Moreover, they have a conserved N-terminal proline, which plays an important catalytic role. Mechanistic, NMR, and pH rate studies of the two dehalogenases, coupled with a crystal structure of CaaD inactivated by 3-bromopropiolate, indicate that they use a general acid/base mechanism to catalyze the conver...Continue Reading

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Citations

Nov 20, 2008·Acta Crystallographica. Section D, Biological Crystallography·Scott D PeganAndrew D Mesecar
Mar 13, 2013·Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences·Pablo I NikelVíctor de Lorenzo
Nov 29, 2005·Environmental Microbiology·Dick B JanssenPeter Terpstra
Jan 8, 2015·Biochemistry·Bert-Jan BaasGerrit J Poelarends
Feb 11, 2011·Bioscience, Biotechnology, and Biochemistry·Tatsuo Kurihara
May 23, 2013·Biochemistry·Gottfried K SchroederChristian P Whitman
Dec 2, 2011·Journal of the American Chemical Society·Gottfried K SchroederChristian P Whitman
Mar 28, 2008·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Tatsuo Kurihara, Nobuyoshi Esaki
May 8, 2013·Chembiochem : a European Journal of Chemical Biology·Bert-Jan BaasGerrit J Poelarends
May 23, 2012·Chembiochem : a European Journal of Chemical Biology·Anna A WasielGerrit J Poelarends

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