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  • Title: Large-scale chemical and chemo-enzymatic synthesis of a spacer-containing Pk-trisaccharide.
    Author: Kamath VP, Yeske RE, Gregson JM, Ratcliffe RM, Fang YR, Palcic MM.
    Journal: Carbohydr Res; 2004 Apr 28; 339(6):1141-6. PubMed ID: 15063203.
    Abstract:
    The Pk-trisaccharide, linked to a solid carrier, is a potential agent for neutralization of shiga-like toxin in the gastrointestinal tract. Two approaches to the multigram-scale synthesis of a linkable Pk-trisaccharide derivative were therefore investigated. A four-step chemical synthesis yielded 8-methoxycarbonyloctyl beta-lactoside in 75% yield from lactose. Further conversion of this derivative through either multistep organic synthesis or one-step enzymatic galactosylation with UDP-galactose and recombinant alpha-1,4-galactosyltransferase gave the Pk-trisaccharide derivative 8-methoxycarbonyloctyl alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside in 25% and 68% overall yields from commercial lactose, respectively.
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