Esters of trehalose from Corynebacterium diphtheriae: A modified purification procedure and studies on the structure of their constituent hydroxylated fatty acids |
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Authors: | David W. Thomas Amabile K. Matida Célio L. Silva Thuioshi Ioneda |
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Affiliation: | SRI International, Menlo Park, CA U.S.A.;Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, São Paulo Brasil |
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Abstract: | The purification procedure of 6,6′-diesters of trehalose from Corynebacterium diphtheriae was modified and the isolated substance was analysed by mass spectrometry as its permethylated derivative. The fatty acid moiety released from the glycolipid after alkaline hydrolysis was studied by mass spectral analysis of the O-methylated and O-acetylated methyl ester derivatives. By argentation thin-layer chromatography, three species of O-acetylated methyl esters were recognized, corresponding to saturated, mono-unsaturated and di-unsaturated α-branched-β-hydroxylated fatty acids. The double bond was located by ozonolysis of the O-acetylated methyl ester derivatives, by gas chromatography of the reaction product and mass spectrometry of the effluent from the gas chromatograph. The main components of each species of α-branched-β-hydroxylated fatty acids found in the gly colipid fraction of C. diphtheriae were 2-tetradecyl-3-hydroxyoctadecanoic acid (C32H64O3, corynomycolic acid), 2-tetradecyl-3-hydroxy-11-octadecenoic acid (C32H62O3, corynomycolenic acid), 2-tetradec-7′-enyl-3-hydroxy octadecanoic acid (C32H62O3) and 2-tetradec-7′-enyl-3-hydroxy-11-octadecenoic acid (C32H60O3, corynomycoldienic acid). The glycolipid fraction from C. diphtheriae is obviously a complex mixture of 6,6′-diesters of trehalose. |
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Keywords: | To whom correspondence should be addressed. |
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