O-specific lipopolysaccharides

Marolda, C.L., Vicarioli, J., Valvano, M.A. Wzx proteins involved in biosynthesis of O antigen function in association with the first sugar of the O-specific lipopolysaccharide subunit. Microbiology 150 (2004) 4095 1105. 

Alkylation of metal chelates of sucrose with allyl halides and sodium bromo-acetate in DMSO yielded mono-O-allylated and mono-O-carboxymethylated derivatives. A new acidic monosaccharide from the O-specific lipopolysaccharide of Shigella dysenteriae type 3 has been identified as 4-0-[(/ )-l-carboxy-ethyl]-D-glucopyranose on the basis of chemical and mass-spectral evidence and by its synthesis by alkylation of methyl 2,3,6-tri-0-benzyl-a(P)-D-glucopyranoside with (5)-2-chloropropionic acid, esterification (with diazomethane), hydrogenolysis, and acid hydrolysis. ... 

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