Synthesis of glycosides of alpha-D-mannopyranose 6-(alpha-D-glucopyranosyl phosphate). The putative ligatin receptor.
p-Nitrophenyl alpha-D-mannopyranoside 6-(alpha-D-glucopyranosyl phosphate) (7) and 6-(alpha-D-galactopyranosyl phosphate) (8) were synthesized by condensation of the appropriate peracetylated glycosyl phosphate with p-nitrophenyl 2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside followed by alkaline deprotection. 1H-, 31P-, and 13C-n.m.r. spectroscopy were used to establish the structures of 7 and 8, and to examine the conformational preferences about the phosphoric diester linkage.
D002236:Carbohydrate Conformation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008565:Membrane Proteins / Q000378:metabolism*; D009904:Optical Rotation; D011956:Receptors, Cell Surface / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D008565:Membrane Proteins; D011956:Receptors, Cell Surface; D013403:Sugar Phosphates; C013090:ligatin; C047815:4-nitrophenyl-(alpha)-mannopyranoside 6-(alpha-glucopyranosyl phosphate); C047816:4-nitrophenyl-alpha-mannopyranoside 6-(alpha-galactopyranosyl phosphate)