A family of diacyltrehaloses isolated from Mycobacterium fortuitum.
A trehalose-containing glycolipid was detected in several strains of Mycobacterium fortuitum and characterized as 2,3-di-O-acyltrehalose (DAT) by combined NMR spectroscopy, IR spectroscopy, GLC and GLC-MS. Lipid 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% straight-chain acyl substituents (hexadecanoyl and octadecanoyl predominating) and 25-30% 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-III, which was the major isolated fraction, consisted of compounds in which the ratio linear to branched acyl groups varied between 0.8 to 0.9, 2-methyl octadecen-2-oyl, 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-oyl, 2-methyl eicosadienoyl and 2-methyl eicosen-2-oyl groups.
Ariza
M A
MA
Departamento de Genética y Microbiología, Facultad de Medicina, Universidad de Murcia, Spain.
Martín-Luengo
F
F
Valero-Guillén
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PL
D002473:Cell Wall / Q000737:chemistry; D002849:Chromatography, Gas; D005227:Fatty Acids / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009170:Nontuberculous Mycobacteria / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014199:Trehalose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification
D005227:Fatty Acids; D014199:Trehalose