Isolation and Chemical Characterization of the Peptidyl Factor Inducing Sexual Agglutination in Saccharomyces cereviciae

Ten diether-type monoglycosyl and glycobiosyl glycerolipids, including 3-O-(4-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-l,2,-di-O-n-tetradecyl-sn-glycerol, a synthetic analogue of lactosyl ceramide, were synthesized and their stereochemistry was assigned unambiguously by ¹³C NMR using the values of C-H one bond couplings. Their ¹³C NMR were further analysed to show the diagnostic α-effect of glycosylation in these compounds depending on the anomeric configuration of the glycosyl residue linked to C-3′-O atom.