Abstract
IT has recently been reported by Macfarlane1 that lipoamino-acids are probably of general occurrence in bacteria, and that they may easily be isolated in good yield if a suitable extraction procedure is selected. It was further shown1 that these lipoamino-acids could be characterized with reasonable certainty as O-amino-acid esters of phosphatidyl-glycerol. We now report that some of the lipoamino-acid complexes obtainable from Bacillus megaterium2 appear to have this same structure. The phosphorus-containing fraction1 of Hunter and Goodsall2 was dissolved in ether and shaken at 20° for 30 min with an equal volume of N/15 sodium hydroxide (cf. Macfarlane1). This procedure reduced the nitrogen content of the ether phase from 2.5 per cent to less than 0.1 per cent. At the same time, the lipid became oxidizable by periodic acid with the formation of formaldehyde. Using 0.04 M periodic acid in chloroform–95 per cent acetic acid, 569 µg of the original lipoamino-acid complex yielded 0.69 µmole of formaldehyde after the alkaline treatment (estimated by chromotropic acid; calculation for the O-leucylester of pentadecanoylpalmitylglycerylphosphorylglycerol = 0.71 µmole). After complete hydrolysis of the lipoamino-acid complex, the only organic compound detectable apart from amino- and carboxylic-acids was glycerol, which was isolated as the crystalline tribenzoate.
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References
Macfarlane, M. G., Nature, 196, 136 (1962).
Hunter, G. D., and Goodsall, R. A., Biochem. J., 78, 564 (1961).
Hunter, G. D., and Godson, G. N., Nature, 189, 140 (1961).
Gaby, W. L., Wolin, H. L., and Zajac, I., Cancer Res., 20, 1508 (1960).
James, A. T., Methods of Biochemical Analysis, edit. by Glide, D., 1 (Interscience Publishers, 1961).
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HUNTER, G., JAMES, A. Lipoamino-acids from Bacillus megaterium. Nature 198, 789 (1963). https://doi.org/10.1038/198789a0
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DOI: https://doi.org/10.1038/198789a0
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