Synthesis, NMR, and conformational studies of methyl α-D-mannopyranoside 2-, 3-, 4-, 6-monophosphates

Article abstract of DOI:10.1016/0008-6215(94)00169-3

The syntheses of methyl α-D-mannopyranoside 2-, 3-, 4-, and 6-phosphate disodium salts are described. ¹H, ¹³C, and ³¹P NMR spectra of the four monophosphates were recorded, fully assigned, and compared to nonphosphorylated methyl α-D-mannopyranoside in order to obtain chemical shift changes due to phosphorylation. The magnitude of these changes are up to 0.45 ppm for ¹H and 3.0 ppm for ¹³C NMR spectra. The preferred orientation of the phosphate group in the four compounds was also calculated. The syntheses of methyl α-D-mannopyranoside 2-, 3-, 4-, and 6-phosphate disodium salts are described. ¹H, ¹³C, and ³¹P NMR spectra of the four monophosphates were recorded, fully assigned, and compared to nonphosphorylated methyl α-D-mannopyranoside in order to obtain chemical shift changes due to phosphorylation. The magnitude of these changes are up to 0.45 ppm for ¹H and 3.0 ppm for ¹³C NMR spectra. The preferred orientation of the phosphate group in the four compounds was also calculated.