4,6-Dimethoxy-1,3,5-triazin-2-yl β-d-glycosaminides: Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-β-d-glucosaminidase from Amycolatopsis orientalis

A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl β-d-glucosaminide (GlcN-β-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-β-d-glucosaminidase (GlcNase) from Amycolatopsi...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2012-10, Vol.31 (8), p.634-646
Main Authors: Tanaka, Tomonari, Wada, Tomonori, Noguchi, Masato, Ishihara, Masaki, Kobayashi, Atsushi, Ohnuma, Takayuki, Fukamizo, Tamo, Brzezinski, Ryszard, Shoda, Shin-ichiro
Format: Article
Language:English
Subjects:
Adducts
Amino sugar
Amycolatopsis orientalis
Carbohydrates
Chemo-enzymatic synthesis
Chloride
D-Galactosamine
Dehydrative condensing agent
DMT-glycoside
Enzymatic transglycosylation
Enzymes
Glycosidase
Sugar
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Summary:A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl β-d-glucosaminide (GlcN-β-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-β-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-β-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.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2012.698437