Synthesis and conformational analysis of a lipotetrasaccharide related to the nodulation factor of Rhizobium bacteria

Article abstract of DOI:10.1016/S0957-4166(97)00108-0

The synthesis of the lipotetrasaccharide glycoside, p-methoxyphenyl O-{2-deoxy-2-[(11Z)-11-octadecenoylamido]-β-D- glucopyranosyl}-(1→4)-O-(β-D-glucopyranosyl)-(1→4) O-β-D-glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-β-D- glucopyranoside 16, starting from acetobromocellobiose is reported. Compound 16 is an analogue of the nodulation factors of Rhizobium bacteria having the central chitobiose unit substituted by a cellobiose unit. A conformational study indicates that 16 have restricted fluctuations around the glycosidic torsion angles, but can adopt a variety of shapes.