1Hand13C NMR Assignments of 2.3-Diacetylamido-2,3-Dideoxy-D-Glucopyranose

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Abstract
Lipid A exhibits thp most important biological attributes of lipopolysaccharide (LPS) of gram-negative bacteria including endotoxicity, adjuvanticity and antitu-mor activity.′ The lipid A backbone, in general, is found to consist of a pyranosidic β 1,6-linked D-glucosamine disaccharide [β-D-GlcpN-(1→6)-α-D-GlcpN] phospho-rylated at 1 and 4′ positions and bearing two amide bound and two ester linked hydroxy and/or acyloxy fatty acids.2 However, the lipid A moiety of LPS from var-ious strains of the two gram-negative, photosynthetic bacteria, Rhodopseudomonas virtdia and Rhodopseudomonas palustrts, possesses 2,3-diamino-2,3-dideoxy-D-glucose as a constituent sugar. 3 This diamino sugar has been also reported to occur in LPS from several other bacterial specie4.5 Recently we found that the lipid X of Brucella abortus contains p(1→6)-linked 2,3-diamino-2,3-dideoxy-D- glucopyranose disaccharide moiety with a phosphate group at the 4′ position and amide bound acyloxy and hydroxy fatty acids.6