SYNTHESIS AND CONFORMATIONAL ANALYSIS OF A LIPOTETRASACCHARIDE RELATED TO THE NODULATION FACTOR OF RHIZOBIUM BACTERIA

Abstract The synthesis of the lipotetrasaccharide glycoside, p -methoxyphenylO-{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.