PubMed · 15415496
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R J GORLIN. 1950. Does glucoascorbic acid produce scurvy?. https://doi.org/10.1177/00220345500290021501
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The O-specific polysaccharide was isolated from Yersinia mollaretii strain WS 42/89 and characterized. Studies of the partial hydrolysis and methylation products and the 1H and 13C NMR spectroscopy data enabled the following structure to be proposed for the repeating unit of the polysaccharide: -->2)-beta-D-Galp-(1-->3)-alpha-D-6dGulp-(1--> The same structure was ascribed to the O-specific polysaccharide from Yersinia enterocolitica serovar O:6.31. The difference between these two O-antigens from various Yersinia species is in the absence of D-glycero-D-manno-heptose residues in the structure of the lipopolysaccharide from Y. mollaretii.
Five monophosphates of L-glycero-D-manno-heptose having the PO(OH)2 residue at O-2,3, 4, 6, and 7 have been synthesized starting from suitably protected benzyl D-mannopyranoside derivatives. The synthesis involved chain elongation by the reaction of D-mannoside 6-aldehyde with alkoxymethylmagnesium chloride resulting in the desired L-glycero-D-manno-heptopyranoside as the main product. The blocking groups pattern enabled selective deprotection of the hydroxyl groups at C-2, 3, 4, and 7. These substrates were phosphitylated with 2-dimethylamino-5,6-benzo-1,3,2-dioxaphosphepan and oxidized in situ to phosphates. The resulting products were hydrogenolytically deprotected and converted to di(cyclohexylammonium) salts which were characterized by 13C-NMR spectra.
The structures in aqueous solution of all major contributing forms of D-altro-heptulose 1,7-diphosphate, and D-glycero-D-altro and D-glycero-D-ido-octulose 1,8-diphosphates have been established by 13C-n.m.r. spectroscopy. Assignments to individual carbon atoms were made with the aid of isotopically enriched analogues and by comparison with related sugars.