title: [Fragments of biopolymers containing glycosylphosphates residues. 9. Synthesis of tetra(2-acetamido-2-deoxy-D-glucopyranosyl)triphosphate-- a tetrameric fragment of the capsule antigen from Escherichia coli K51].
abstract: Linear tetra(N-acetylglucosaminyl)triphosphate GlcNAc(alpha)-P-3GlcNAc (alpha)-P-3GlcNAc(alpha)-P-3GlcNAc(beta)-ONp, a fragment of the capsular antigen of E. coli K51, was synthesized by the step-by-step approach with the use of the H-phosphonate method, starting the chain from p-nitrophenyl 2-acetamido-4,6-di-O-benzoyl-2-deoxy-beta-D-glucopyranoside. The elongation cycle included the coupling of 2-acetamido-4,6-di-O-benzoyl-2-deoxy-3-O-p-methoxybenzyl-alpha-D-gluc opy ranosyl H-phosphonate with a hydroxyl component in the presence of Me3CCOCl followed by oxidation (I2) and de (methoxybenzylation) (Ce(NH4)2(NO3)6). 2-Acetamido-3,4,6-tri-O-benzoyl-2-deoxy-alpha-D-glucopyranosyl H-phosphonate was employed in the final step. After mild debenzoylation the title tetramer was isolated by anion-exchange chromatography. The data of 1H, 13C and 31P NMR spectra of the synthesized oligomers are discussed.
authors.forename: A V
authors.initials: AV
authors.lastname: Nikolaev
authors.forename: I A
authors.initials: IA
authors.lastname: Ivanova
authors.forename: V N
authors.initials: VN
authors.lastname: Shibaev
mesh_terms: D000117:Acetylglucosamine / Q000138:chemical synthesis*; D000942:Antigens, Bacterial / Q000737:chemistry*; D001704:Biopolymers; D002240:Carbohydrate Sequence; D002852:Chromatography, Ion Exchange; D004926:Escherichia coli / Q000276:immunology*; D005958:Glucosephosphates / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides
chemical_list: D000942:Antigens, Bacterial; D001704:Biopolymers; D005958:Glucosephosphates; D009844:Oligosaccharides; C076617:tetra(2-acetamido-2-deoxy-glucopyranosyl)triphosphate 4-nitrophenyl; D000117:Acetylglucosamine
vernacular_title: Fragmenty biopolimerov, soderzhashchikh ostatki glikozilfosfatov. 9. Sintez tetra(2-atsetamido-2-dezoksi-D-gliukopiranozil)trifosfata--tetramernogo fragmenta kapsul'nogo antigena Escherichia coli K51.