Synthesis of a Spacer-Linked Derivative of Heptopyranosyl(α1-3)heptopyranose Expressed in Lipooligosaccharide and Lipopolysaccharide

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概要

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• Glycosylation of penta-<I>O</I>-acetyl heptopyranosyl trichloroacetimidate with the 3-OH acceptor, methyl 2-<I>O</I>-benzyl-4,6-<I>O</I>-benzylidene-7,8-dideoxy-α-D-<I>manno</I>-oct-7-enopyranoside, gave the desired α1-3-linked disaccharide in a 94% yield. The oct-enopyranoside moiety of the disaccharide was converted to the heptoside by oxidative cleavage with osmium tetroxide/NaIO<SUB>4</SUB> and subsequent reduction with NaBH<SUB>4</SUB>. The resulting α1-3-linked heptose disaccharide was converted to a tricholoroacetaimidate derivative containing a benzoyl group at C-2. This donor was glycosylated with 2-(carbobenzoxyamino)-1-ethanol to give an α spacer-linked disaccharide derivative in a 90% yield. Zemplén deacylation of the derivative and subsequent hydrogenolysis gave a 2-aminoethyl glycoside of heptopyranosyl(α1-3)heptopyranose.

• Japan Society for Bioscience, Biotechnology, and Agrochemistryの論文
• 2012-04-23

著者

• Yamasaki Ryohei

  Department Of Biochemistry & Biotechnology Tottori University

• Nagahara Kaori

  Department Of Life And Food Sciences Tottori University

• KISHIMOTO Katsuya

  Department of Life and Food Sciences, Tottori University

• TAKAJYO Akihiko

  Department of Life and Food Sciences, Tottori University

関連論文

• Western Blot Analysis of Neisserial Lipooligosaccharide at the Lower Femtomole Level with Normal Human Sera
• Normal Human Sera Contain Bactericidal IgG That Binds to the Oligosaccharide Epitope Expressed within Lipooligosaccharides of Neisseria gonorrhoeae
• Synthesis of a Spacer-Linked Derivative of Heptopyranosyl(α1-3)heptopyranose Expressed in Lipooligosaccharide and Lipopolysaccharide

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