Synthesis of non-natural xyloglucans by polycondensation of 4,6-dimethoxy-1,3,5-triazin-2-yl oligosaccharide monomers catalyzed by endo- β -1,4-glucanase

Tomonari Tanaka, Masato Noguchi, Masaki Ishihara, Atsushi Kobayashi, Shin Ichiro Shoda

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Summary: A cellotetraose-backboned hepta-saccharide (XXXG) (a capital X represents a glucopyranose residue that is substituted with a xylopyranose through an α-1,6 glycosidic bond, and a capital G represents a non-substituted glucopyranose residue) and a nona-saccharide (XLLG) (a capital L represents a glucopyranose residue that is substituted with a galactopyranoseβ(1-2)xylopyranose through an α-1,6 glycosidic bond) have directly been converted to the corresponding 4,6-dimethoxy-1,3,5-triazin-2- yl derivatives (DMT-β-XXXG 1 and DMT-β-XLLG 2, respectively) by the action of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl morpholinium chloride (DMT-MM). The selective nucleophilic attack of the anomeric hydroxyl group to DMT-MM has been achieved in water without using any protection of the hydroxyl groups. The resulting activated oligosaccharide derivatives (1 and 2) were found to polymerize catalyzed by an endo-β-1,4-glucanase as catalyst. The polymerization took place in a complete regio- and stereo-selective manner, affording non-natural polysaccharides having a XXXG-repeating unit and a XLLG-repeating unit, respectively, in the main chain. It is extremely difficult to construct such definite repeating structures via the conventional synthetic routes including protection-deprotection procedures.

Original languageEnglish
Pages (from-to)200-209
Number of pages10
JournalMacromolecular Symposia
Volume297
Issue number1
DOIs
Publication statusPublished - 2010 Nov 1

Keywords

  • DMT-β-glycoside
  • endo-β-1,4-glucanase
  • enzyme
  • polycondensation
  • xyloglucan

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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