Isolation and characterization of d-allobisnorbiotin.
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Biomedical subjects
Publications and source records attributed to L D Wright.
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Pseudomonas putida LP, which grows on lipoate, NH4NO3 and mineral salts, converts most of the organic substrate to bisnor-lipoate (1,2-dithiolane-3-propanoic acid) and acetyl-CoA. D-, L-, or DL-lipoate serve equally well as carbon and sulphur sources. There was no growth on or bacterial oxidation of the chemically synthesized bisnor- or tetranor-(1,2-dithiolane-3-carboxylic acid) chain-shortened analogues, but these, as well as lipoate, could supply the sulphur needed for growth when acetate was provided as the sole source of carbon. The uptake of lipoate by the bacterium is very slow and non-inducible, while the uptake of acetate is faster than octanoate. The oxidation of octanoate is more rapid and extensive than that of lipoate. Levels of acyl-CoA synthetase are not affected by the source of carbon, but activities of isocitrate lyase and malate synthase are higher when the cells are grown in acetate, octanoate or lipoate and lower when glucose is the carbon source. The glyoxylate cycle is induced to facilitate utilization of acetyl-CoA derived from lipoate, which is also degraded to water-soluble catabolites that yield the much smaller amount of sulphur required for growth.
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A strain of bacteria that can degrade lipoic acid was isolated from soil. The bacterium, adapted to use 0.4% dl-lipoate as the sole organic substrate to supply carbon, sulfur, and energy, was identified morphologically and physiologically as a strain of Pseudomonas putida. Degradation of 1,6-(14)C-lipoic acid, synthesized from 1,6-(14)C-adipic acid, was evidenced by: (i) loss of approximately 50% of the total radioactivity from the medium after bacterial growth; (ii) appearance of (14)C-degradation products upon paper and thin-layer chromatography of the culture medium; and (iii) oxygraphically measured utilization of O(2) by cells in the presence of lipoate or other oxidizable substrates. Analyses of the benzene extract of culture medium by infrared, nuclear magnetic resonance, and mass spectrometry, and by gas-liquid chromatography after desulfuration, have characterized bisnorlipoic acid, or 4,6-dithiohexanoic acid, as the major catabolite present in the medium. beta-Oxidation of the side chain is thus proven to be a pathway employed by the pseudomonad to degrade lipoic acid.
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Intermediates formed during the microbial degradation of imidazole, namely 4(5)-imidazolone, formiminoglycine, and possibly glycine, are similar to those formed during metabolism of imidazole derivatives.
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