Synthesis of the optically active 4-O-phosphono-D-glucosamine derivatives related to the nonreducing-sugar subunit of bacterial lipid A.
The optically active lipid A-subunit homologs named GLA-46, GLA-47, GLA-59, and GLA-60 have been synthesized stepwise by successive acylation at N-2 and O-3 of benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside with the 3-9O-(benzyloxy)methyl or 39O-tetradecanoyl derivative of optically active 3-hydroxytetradecanoic acid, and phosphorylation at O-4 of the D-glucosamine residue.
D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D008050:Lipid A; D013403:Sugar Phosphates; D005944:Glucosamine