An approach to the chemical synthesis of the natural capsular polysaccharide from Streptococcus pneumoniae type 3
V. I. Betaneli, A. Ya. Ott
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: Chemical synthesis of the heteropolysaccharide derivative [→4)-β-D-Glcp(l→3)-α, β-D-GlcpUA(l→]n using the tritylcyanoethylidene condensation method is carried out. The polysaccharide consists, in average, of ten disaccharide fragments, with a 1,2-cis-glucopyranosiduronic linkage per three disaccharide units. The sodium borohydride reduction followed by deacetylation afforded glucan, consisting of glucopyranosidic units and sorbitol on the “reducing” end. The monomer, methyl-4-O-acetyl-3-O-(2,3,6-tri-O-acetyl-4-O-triphenylmethyl-β-D-glucopyranosyl)-1,2-O-(1-exo-cyano)ethylidene - α-D-glucopyranuronate, for the polycondensation was synthesized from D-Glc. The product of the tritylcyanoethylidene condensation contains grouping(s) yielding the aromatic atom signals in 1H and 13C NMR spectra.
Russian Journal of Bioorganic Chemistry 1991, 17 (10):1390-1400