ABSTRACT
An enantioselective de novo synthesis of a thioglycoside derivative of the 6-O-methyl-D-glycero-L-gluco-heptopyranose residue found in the Campylobacter jejuni NCTC11168 (HS:2) capsular polysaccharide is reported. The compound is obtained from a furfural-derived chiral diol in 11 steps. Notably, compared to the only previous synthesis of this molecule, this approach significantly reduces the number of purification steps required to obtain the target.
Subject(s)
Campylobacter jejuni/chemistry , Glycerol/analogs & derivatives , Monosaccharides/chemical synthesis , Polysaccharides/chemistry , Thioglycosides/chemistry , Bacterial Capsules/chemistry , Glycerol/chemical synthesis , Glycerol/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Monosaccharides/chemistry , Stereoisomerism , Thioglycosides/analysisABSTRACT
The first synthesis of the 6-O-methyl-D-glycero-α-L-gluco-heptopyranose moiety present in the capsular polysaccharide from Campylobacter jejuni NCTC 11168 is reported. The target (1) was synthesized as the 8-aminooctyl glycoside and then conjugated to bovine serum albumin (BSA) for the generation of antibodies recognizing this motif. Heptose 1 was obtained from D-galactose via a series of galactofuranose derivatives.
