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Acinetobacter strain 210A has been grown in batch and continuous cultures in an acetate medium. The P content of the cells varied from 6–10% of the dry matter and phosphate uptake continued for months as long as carbon and nitrogen source, inorganic salts and oxygen were present. The growing ( = metabolizing) bacterial cells released phosphate under anaerobic conditions. Addition of CO2, acetate and ethanol or other reduced carbon sources stimulated the rate of the phosphate release but after 24 hours of anaerobiosis the obtained results with or without additions were similar.

When cultured in stirred fermentors the yeast Candida bogoriensis produces extracellular glycolipids in yields of 0.5 to 1 g/l. The principal component of these is a crystalline sophorosyl hydroxy fatty acid, the structure of which has been established as 13-[(2'-0-13-D-glucopyranosyl-8-n-glucopyranosy1)-oxy]docosanoic acid 6',6"-diacetate. The hydroxy acid portion of the molecule probably has the L-configuration. A monoacetyl glycolipid is also present as a minor component.Canadian Journal of Chemistry, 46, 345 (1968) Deinema (I) discovered that the yeast Candida bogoriensis, which had been isolated from the leaf surface of the shrub Randia malleiJera in Indonesia, produced insoluble extracellular acidic glycolipids when grown on a glucose-yeast extract medium. Sometimes the product appeared as crystals but on other occasions it separated as viscous droplets from which, however, crystalline inaterial could usually be isolated. The crystalline glycolipid is now shown to be 13-[(2'-0-0-D-glucopyranosyl-0-D-glucopyranosyl)oxy]docosanoic acid 6',6"-diacetate (1). The total yield of crystalline glycolipid varied from a half to one tenth of this. However, chromatography of the crude glycolipid as methyl esters showed that, in fact, it contained about 50 % of the diacetyl sophoroside, 10-15 % of the remainder appeared to be a monoacetyl sophoroside, and the rest consisted of unsaturated 18-carbon fatty acids.Alkaline hydrolysis of the glycolipid gave about two moles of acetic acid per mole of glycolipid; acid methanolysis yielded about one mole of methyl 13-hydroxydocosanoate and about two moles of methyl cub-D-glucopyranosides. Reduction of the fatty acid ester gave lNRCC No. 9862. methyl docosanoate. Oxidative cleavage gave two dicarboxylic acids, dodecanedioic and tridecanedioic acids, indicating that the hydroxyl group was at carbon-13. Methyl 13-oxodocosanoate, indistinguishable from material synthesized by the 12-carbon chain extension method of Hiinig and Buysch (2), was obtained by mild oxidation.The hydroxy docosanoate from the glycolipid has a very low optical rotation at the D line, but optical rotatory dispersion (0.r.d.) measurements show that it has a positive plain dispersion curve. Since 9-D-, 10-D-, and 12-D-hydroxyoctadecanoates have negative dispersion curves (3), the present acid probably has the L-configuration. The other hydroxy acid isolated from extracellular yeast lipids, 17-hydroxyoctadecanoic acid from Torulopsis apicola (4), also has the L-configuration suggesting that hydroxy acids from yeasts have configurations opposite to those from plants. Monohydroxydocosanoic acids, substituted near the center of the chain, do not appear to have been found previously, though it is of interest that an unidentified species of yeast produces the triacetate of 8,9,13-trihydroxydocosanoic acid (5).Complete methylation of the glycolipid (4) yielded a hepta-0-methyl methyl ester which on Can. J. Chem. Downloaded from www.nrcresearchpress.com by 52.41.17.47 on 05/07/18For personal use only.

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