[The occurrence of a reductase of delta2-carboxylic acids in Clostridium kluyveri with a stereospecificity different from that of butyryl-CoA dehydrogenase (author's transl)].
A Clostridia strain (R-strain) which hydrogenates tiglinate (1b) and alpha-methylcinnamate (1c) in the presence of hydrogenase gas in 2H2O to (2R, 3S)2-methyl-[2,3-2H]butyrate (5b, H = 2H) and (alphaR, betaR)alpha-methyl[alpha,beta-2H]dihydrocinnamate (5c, H = 2H), respectively, was isolated. The configuration at C-3 was determined by 1H-NMR spectroscopy in the presence of Eu(fod)3. The stereochemistry of this hydrogenation is the mirror image of that which has been determined with intact cells of another strain of Clostridium kluyveri (S-strain). In the presence of hydrogen gas, the R-strain hydrogenates crotonate in 2H2O to butyrate with the following deuterium distribution: C-2, 1.85; C-3, 1.35; and C-4, 0.63 deuterium atoms. Crotonate seems to be the substrate of two reductases with sterically different actions. Tiglinate (1b) and alpha-methylcinnamate, however, are hydrogenated only by that reductase which is different from the butyryl-CoA dehydrogenase.
D002087:Butyrates; D002264:Carboxylic Acids; D003013:Clostridium / Q000201:enzymology*; D003065:Coenzyme A; D010088:Oxidoreductases / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002087:Butyrates; D002264:Carboxylic Acids; D010088:Oxidoreductases; D003065:Coenzyme A
Uber des Vorkommen einer Reduktase von delta2-Carbonsäuren in Clostridium kluyveri mit einer von der Butyryl-Coa-dehydrogenase verschiedenen Stereospezifität