A trehalose-containing glycolipid was detected in several strains of Mycobacteriutn fortuitum and characterized as 2,3-di-O-acyltrehaIose (DAT) by constituents of the molecule were identified as a mixture of straight-chain (14-18 carbon atoms) and methyl-branched-chain (17-21 carbon atoms) fatty acyl groups. DAT was further fractionated by reverse phase TLC into four fractions that were designated DAT-I-DAT-IV. DAT-I contained 70-75 O/ O straightchain acyl substituents (hexadecanoyl and octadecanoyl predominating) and 25-30 O/ O 2-methyl branched substituents (mainly 2-methyl octadecadienoyl). DAT-II was composed of a mixture in which the acyl groups were almost exclusively 2-methyl branched, with 2-methyl octadecadienoyl and 2-methyl octadecen-2-oyl predominating. DAT-Ill, which was the major isolated fraction, consisted of compounds in which the ratio linear to branched acyl groups varied between 0.8 to 09,2-methyl octadecen-2-oy1, hexadecanoyl and octadecanoyl being the most abundant. Finally, DAT-IV comprised a mixture of DAT molecules containing mostly 2-methyl octadecadienoyl, 2-methyl octadecen-2-oy1, 2-methyl eicosadienoyl and 2-methyl eicosen-2-oyl groups.combined NMR spectroscopy, IR spectroscopy, GLC and GLC-MS. Lipid
A family of 2,3-di-O-acyl trehaloses (DAT), previously identified in Mycobacterium fortuitum, was studied by fast-atom bombardment mass spectrometry to establish the combinations of fatty acyl substituents and, hence, to delineate the molecular species there comprised. The mass spectra indicated the possible existence of 41 molecular species, with a total of 35-40 carbon atoms and 0-4 double bonds in the lipid moiety. The principal components were situated a m/z (M+ +23) 919 (formulated as 2-methyloctadec-2-enoyl,2-methyloctadecadienoyl trehalose and as 2-methylhexadec-2-enoyl,2-methyleicosadienoyl trehalose) and m/z (M+ +23) 921 (formulated as di-2-methyloctadec-2-enoyl trehalose and as 2-methylhexadec-2-enoyl,2-methyleicos-2-enoyl trehalose). The data obtained revealed that DAT was composed of three types of combinations of fatty acyl groups; (i) linear plus linear; (ii) linear plus 2-methyl branched; and (iii) 2-methyl branched plus 2-methyl branched.
A family of 2,3-di-O-acyl trehaloses (DAT), previously identified in Mycobacterium fortuitum, was studied by fast-atom bombardment mass spectrometry to establish the combinations of fatty acyl substituents and, hence, to delineate the molecular species there comprised. The mass spectra indicated the possible existence of 41 molecular species, with a total of 35-40 carbon atoms and 0-4 double bonds in the lipid moiety. The principal components were situated a m/z (M+ +23) 919 (formulated as 2-methyloctadec-2-enoyl,2-methyloctadecadienoyl trehalose and as 2-methylhexadec-2-enoyl,2-methyleicosadienoyl trehalose) and m/z (M+ +23) 921 (formulated as di-2-methyloctadec-2-enoyl trehalose and as 2-methylhexadec-2-enoyl,2-methyleicos-2-enoyl trehalose). The data obtained revealed that DAT was composed of three types of combinations of fatty acyl groups; (i) linear plus linear; (ii) linear plus 2-methyl branched; and (iii) 2-methyl branched plus 2-methyl branched.
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