The O-SPs of the two strains of V. cholerae O1, Ogawa and Inaba, consist of a chain of 15-20 (1®2)-a-linked repeats of 4-amino-4,6-dideoxy-D-mannopyranose (D-perosamine), where the amino group is acylated with 3-deoxy-L-glycero-tetronic acid. The two serotypes differ in that the terminal, upstream residue is methylated at O-2 in the Ogawa O-SP. Here we report the first synthesis of the 18-mer of the monosaccharide repeat, which is, essentially, the complete O-antigen of serotype Inaba. On the way towards the octadecasaccharide, we used a mono-, tri- and hexasaccharide glycosyl donors, containing 4-azido group as a latent amino group. These were coupled with suitable glycosyl acceptors. The dodecasaccharide was built viacoupling of a hexasaccharide donor and a hexasaccharide acceptor. The corresponding octadecasaccharide was built viacoupling of a hexasaccharide donor and a dodecasaccharide acceptor. D-Perosamine being a rare sugar, we had to make its immediate precursor on a few hundred gram scale from the commercially available methyl a-D-mannopyranoside. Many reaction protocols involved have been substantially improved, compared to the conversions developed earlier, and gave the desired products in excellent yields and with high stereoselectivity. Most intermediates were obtained in the analytically pure state and were fully characterized for the first time.

Synthesis of the complete O-antigen of Vibrio choleraeO1, serotype Inaba

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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