4,6-dimethoxy-1,3,5-triazin-2-yl-d-glycosaminides: Novel substrates for transglycosylation reaction catalyzed by exo-d-glucosaminidase from amycolatopsis orientalis

Tomonari Tanaka, Tomonori Wada, Masato Noguchi, Masaki Ishihara, Atsushi Kobayashi, Takayuki Ohnuma, Tamo Fukamizo, Ryszard Brzezinski, Shin Ichiro Shoda

研究成果: Article査読

6 被引用数 (Scopus)

抄録

A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl-d-glucosaminide (GlcN-DMT), has been prepared by the reaction of d-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-d-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to d-galactosamine (GalN). GalN-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.

本文言語English
ページ(範囲)634-646
ページ数13
ジャーナルJournal of Carbohydrate Chemistry
31
8
DOI
出版ステータスPublished - 2012 10月 1

ASJC Scopus subject areas

  • 生化学
  • 有機化学

フィンガープリント

「4,6-dimethoxy-1,3,5-triazin-2-yl-d-glycosaminides: Novel substrates for transglycosylation reaction catalyzed by exo-d-glucosaminidase from amycolatopsis orientalis」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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