GLC-MS OF PARTIALLY METHYLATED AND ACETYLATED DERIVATIVES OF L-GLYCERO-D-MANNO-HEPTOPYRANOSE AND D-GLYCERO-D-MANNO-HEPTOPYRANOSES AND D-GLYCERO-D-MANNO-HEPTITOLS

Methylated or acetylated heptopyranose derivatives were prepared variously from l-glycero-d-manno- and d-glycero-d-manno-heptopyranose, O-l-glycero-a-d-manno-heptopyranosyl-(1 → 3)-l-glycero-d-manno-heptopyranose, O-l-glycero-a-d-manno-heptopyranosyl-(1 → 7)-l-glycero-d-manno-heptopyranose, and O-l-glycero-a-d-manno-heptopyranosyl-(1 → 7)-O-l-glycero-a-d-manno-heptopyranosyl-(1 → 3)-l-glycero-d-manno-heptopyranose, which are structural elements of the heptose region of enterobacterial lipopolysaccharides. Each derivative was investigated by g.l.c. and g.l.c.-m.s., and the retention times and fragmentation patterns were used to identify partial structures of the heptose region of the core oligosaccharide of bacterial LPS. © 1990.