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

摘要

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.View full textDownload full textKeywords:Amino sugar, Chemo-enzymatic synthesis, Glycosidase, Enzymatic transglycosylation, Dehydrative condensing agent, DMT-glycosideRelated var addthis_config = { ui_cobrand: "Taylor & Francis Online", services_compact: "citeulike,netvibes,twitter,technorati,delicious,linkedin,facebook,stumbleupon,digg,google,more", pubid: "ra-4dff56cd6bb1830b" }; Add to shortlist Link Permalink http://dx.doi.org/10.1080/07328303.2012.698437