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

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