Phenylalanineの一代謝産物について
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概要
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It was found that Aspergillus sojae was grown on the Czapek medium containing L-phenylalanine (pH 5.5) and the substance giving green color with ferric chloride was formed in the culture broth. This substance was extracted from the broth with ether and fractionated by silica-gel chromatography. The eluate with solvent (n-hexane: ether=9:1, v/v) was evaporated and crystallized from hot n-hexane. The properties of this crystal were as follows. 1. Melting point of this acidic crystal was 147_??_148°C. 2. Molecular weight was 164 by mass spectrometry. 3. Mass spectra showed the presence of a benzene ring (m/e:91). 4. Infra red spectra in KBr disk showed the presence of a hydroxy group (absorption:3475cm-1). 5. The crystal was an unsaturated compound by Baeyer's test. 6. The reaction with 2, 4-dinitrophenylhydrazine was not detected. 7. One of the degradation products of the crystal by potassium permanganate was identified as benzoic acid. From above properties, the structure of the crystal was presumed as follow (A)._??_ And the reduction product of the crystal by alminum amalgam was identified as synthesized DL-phenyllactic acid by mp, UV and IR spectra.