Biosynthesis of ethylene from methionine. Isolation of the putative intermediate 4-methylthio-2-oxobutanoate from culture fluids of bacteria and fungi.
Methods are described for identifying the 2,4-dinitrophenylhydrazones of 4-methylthio-2-oxobutanoate by means of t.l.c., n.m.r. and mass spectroscopy. By using these methods 4-methylthio-2-oxobutanoate, a putative intermediate in the biosynthesis of ethylene from methionine, has been identified in culture fluids of Aeromonas hydrophila B12E and a coryneform bacterium D7F grown in the presence of methionine. Relative to 4-methylthio-2-oxobutanoate, the yield of 3-(methylthio)propanal (methional) from the same cultures was less than 1%. Because 4-[2H]methylthio-2-oxobutanoate was obtained from cultures grown on [Me-2H]methionine, the 4-methylthio-2-oxobutanoate must be derived from methionine. By means of t.l.c. alone, 4-methylthio-2-oxobutanoate was identified in the culture fluids of a range of bacteria, the yeast Saccharomyces cerevisiae and the fungus Penicillium digitatum. A photochemical assay developed for 4-methylthio-2-oxobutanoate shows it to be a product of the metabolism of methionine by Escherichia, Pseudomonas, Bacillus, Acinetobacter, Aeromonas, Rhizobium and Corynebacterium species.
D001419:Bacteria / Q000378:metabolism; D004136:Dinitrobenzenes; D005030:Ethylenes / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism; D005947:Glucose / Q000378:metabolism; D006835:Hydrazones; D006863:Hydrogen-Ion Concentration; D007651:Keto Acids / Q000378:metabolism; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008715:Methionine / Q000031:analogs & derivatives* / Q000378:metabolism*; D013045:Species Specificity
C001072:2,4-dinitrophenylhydrazone; D004136:Dinitrobenzenes; D005030:Ethylenes; D006835:Hydrazones; D007651:Keto Acids; C014632:2-keto-4-methylthiobutyric acid; D008715:Methionine; D005947:Glucose