Nicotinic Acid Metabolism. Dimethylmaleate Hydratase
- 1 January 1984
- journal article
- research article
- Published by Walter de Gruyter GmbH in Hoppe-Seyler´s Zeitschrift Für Physiologische Chemie
- Vol. 365 (2), 847-858
- https://doi.org/10.1515/bchm2.1984.365.2.847
Abstract
The partial enrichment of a new enzyme, dimethylmaleate hydratase from Clostridium barkeri and some of its characteristics are described. The unstable and O2-sensitive hydratase depends on ferrous ions and is induced during growth of C. barkeri on nicotinic acid. The enzyme uses both dimethylmaleate and the hydration product, 2,3-dimethylmalate, as substrates to establish an equilibrium that is 60% in favor of the latter acid; dimethylfumarate is not attacked. A 2,3-dimethyl[3-3H]malate specimen was prepared from dimethylmaleate with the hydratase in tritiated water. Based on proton attack at the re-face of the double bond, experimental results indicate the (2R,3S)-configuration for this malate. The hydration reaction takes an anti-course. The tritium label was lost in the sequence (2R,3S)-2,3-dimethyl[3-3H]malate .fwdarw. (R)-[2-3H1]-propionate .fwdarw. (2R)-[2-3H1]propionyl-CoA .fwdarw. (2S)-methylmalonyl-CoA. This result confirms the stereochemical course of the 2,3-dimethylmalate lyase reaction, inversion of configuration, by an independent approach. The hydratase reaction completes the degradation scheme of nicotinic acid by C. barkeri. The pathway is briefly reviewed.This publication has 16 references indexed in Scilit:
- Nicotinic Acid Metabolism. Stereochemical Course of the (2R, 3S)-2,3-Dunethylmalate Lyase ReactionHoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1982
- Nicotinic Acid Metabolism. Enzymic Preparation and Absolute Configuration of the Substrate for 2,3-Dimethylmalate LyaseHoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1980
- Nicotinic Acid Metabolism. 2,3-Dimethylmalate LyaseHoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1979
- Enzyme Reaction Stereospecificity: A Critical RevieCRC Critical Reviews in Biochemistry, 1972
- Nicotinic Acid MetabolismPublished by Elsevier ,1971
- Nicotinic Acid MetabolismPublished by Elsevier ,1971
- Stereochemie der enzymatischen Carboxylierung von (2R)‐2‐3H‐Propionyl‐Coenzym AHelvetica Chimica Acta, 1966
- Nicotinic Acid MetabolismPublished by Elsevier ,1964