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J Bacteriol. 1978 January; 133(1): 185-195
Copyright © 1978 American Society for Microbiology. All Rights Reserved.

Biosynthesis of Oligosaccharide-Lipid in Streptococcus sanguis

¹ Department of Microbiology, University of Pittsburgh School of Dental Medicine, Pittsburgh, Pennsylvania 15261

ABSTRACT

An oligosaccharide-lipid containing N-acetyl D-glucosamine (GlcNAc), L-rhamnose, and D-glucose was synthesized when the particulate enzyme from Streptococcus sanguis was incubated with UDP-GlcNAc, TDP-rhamnose, and UDP-glucose. The incorporation of D-glucose into the lipid was dependent on the preincorporation of L-rhamnose, which in turn was dependent on that of GlcNAc. This indicates that the order of sugar incorporation is GlcNAc, L-rhamnose, and D-glucose. The synthesis of GlcNAc-lipid was stimulated twofold by ATP and was inhibited strongly by UDP and slightly by UMP, CDP, and TDP, but not by all other nucleoside diphosphates and nucleoside monophosphates tested. A [-³²P]ATP labeling experiment indicated that some acceptor lipid was present in nonphosphorylated form. The acid and alkaline stabilities of the GlcNAc-lipid were similar to those of glycosyl undecaprenylphosphate, and the thin-layer chromatographic mobility of the lipid was slightly faster than that of the mannosylphosphorylundecaprenol. The molar ratio of phosphate to GlcNAc in purified GlcNAc-lipid was found to be 0.96:1. These results suggested that the GlcNAc was attached to the lipid moiety, presumably undecaprenol, by phosphodiester bonds. The incorporation of L-rhamnose into the lipid was inhibited by UDP and UMP, respectively, in a manner similar to the incorporation of GlcNAc. This suggested that the oligosaccharide was also linked to the lipid moiety by phosphodiester bonds.