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Tandem exploitation of Helix pomatia glycosyltransferases: Facile syntheses of H-antigen-bearing oligosaccharides

机译:螺旋果糖糖基转移酶的串联开发:含H抗原的寡糖的简便合成

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摘要

Snails from the family Helicidae produce in their albumen glands a highly branched galactan, which consists almost exclusively Of D- and L-galactose. The D-Gal residues are glycosyclically beta(1 -> 6)- or beta(1 -> 3)-linked, whereas the L-Gal moieties are attached alpha(1 -> 2). Up until the present time, two beta(1 -> 6)-D-galactosyl transferases and one alpha(1 -> 2)-L-galactosyl transferase have been identified in a membrane preparation of these glands. These were used to synthesise various oligosaccharides by successive addition of the NDP-activated (NDP=nucleoside-5'-diphosphate) D-Gal or L-Fuc moieties, up to a heptasaccharide by starting from the disaccharide D-Gal-beta(1 -> 3)-D-Gal-beta(l -> OMe. Even larger oligosaccharides up to a tridecasaccharide were obtained by starting with the hexasaccharide D-Gal-[beta(1 -> 3)-D-Gal](4)-beta(1 -> 4)-D-Glc as an acceptor substrate. This tandem exploitation process has high potential for the easy introduction Of D-Gal and L-Fuc residues into a great variety of oligosaccharides, which can be used in ligand/acceptor studies.
机译:Helicidae家族的蜗牛在其蛋白腺中产生高度分支的半乳聚糖,该半乳聚糖几乎完全由D-和L-半乳糖组成。 D-Gal残基通过糖基β(1-> 6)-或beta(1-> 3)连接,而L-Gal部分则连接alpha(1-> 2)。直到目前,在这些腺体的膜制剂中已经鉴定出两种β(1→6)-D-半乳糖基转移酶和一种α(1→2)-L-半乳糖基转移酶。通过连续添加NDP活化的(NDP = nucleoside-5'-diphosphate)D-Gal或L-Fuc部分将它们用于合成各种寡糖,从二糖D-Gal-beta(1 -> 3)-D-Gal-β(1-> OMe。从六糖D-Gal- [β(1-> 3)-D-Gal](4)开始,可获得更大的寡糖,直至十三糖-β(1-> 4)-D-Glc作为受体底物。这种串联开发过程具有将D-Gal和L-Fuc残基轻松引入各种寡糖的高潜力,这些寡糖可用于配体/接受者研究。

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