Fragments of biopolymers containing glycosyl phosphate residues. 8: Hydrogenphosphonate synthesis of glucosyl phosphosugars containing α-D-glucopyranosyl phosphate and 2-acetamido-2-deoxy-α-D-glucopyranosyl phosphate residues, fragments of bacteria capsular antigens and of glycoproteins
G. I. Eliseyeva, I. A. Ivanova, A. V. Nikolaev, V. N. Shibaev
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow
Abstract: The hydrogenphosphonate method was used for synthesis of a number of phosphate diester (Glc(α)-P-6Man, GlcNAc(α)-P-6Man, GlcNAc(α)-P-3GlcNAc, GlcNAc(α)-P-4GlcNAc) methyl or p-nitrophenyl glycosides. The glycosyl phosphosugars, fragments of the E. coli K51 and N. meningitidis X K-antigens and of several glycoproteins, were obtained by H-phosphonylation of suitable monohydroxyl sugar derivatives with 2,3,4,6-tetra-O-benzoyl-α-D-glycopyranosyl H-phosphonate or 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranosyl H-phosphonate in the presence of Me3CCOCl followed by oxidation and deprotection. The data of 1H, 13C and 31P NMR spectra of the synthesized phosphate diesters are reported.
Russian Journal of Bioorganic Chemistry 1991, 17 (10):1401-1411