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J. Biol. Chem., Vol. 262, Issue 10, 4580-4586, Apr, 1987

Biosynthesis of the mycobacterial O-methylglucose lipopolysaccharide. Characterization of putative intermediates in the initiation, elongation, and termination reactions

K Kamisango, A Dell and CE Ballou

From the 70% ethanol extract of Mycobacterium smegmatis cells, we isolated a mixture of weakly acidic oligosaccharides composed mainly of glucose and 6-O-methylglucose. The elution pattern from a Bio-Gel P-4 column suggested that the oligosaccharides were smaller than the O- methylglucose polysaccharide (MGP) and could be biosynthetic precursors. Analysis by fast-atom-bombardment mass spectrometry revealed that the oligosaccharides fit into a pattern for polysaccharide synthesis based on an alternate glucosylation- methylation mechanism until the chain reached the composition methylglucose11glucose5glyceric acid, at which time 2 glucose units are added to give glucose2methylglucose11glucose5glyceric acid. The addition of the last 2 glucoses and methylation of one of them to give mature MGP (methylglucose1glucose3methylglucose11glucose5glyceric acid) apparently occurs rapidly because the expected intermediates were not observed. Only 4 glucose units are present at the glyceric acid end of some molecules during all stages of the elongation process, and these represent precursors of a minor MGP homolog with an extra methyl group on the beta 1----3-linked glucose unit of MGP. alpha-D-Glucopyranosyl- (1----2)-D-glyceric acid and alpha-D-glucopyranosyl-(1----6)-alpha-D- glucopyranosyl-(1----2)-D-glycer ic acid were also isolated from the extract and correspond in structure to the expected initial precursors.
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