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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 β-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 α-1,4-galactosyltransferase gave the Pk-trisaccharide derivative 8-methoxycarbonyloctyl α-d-galactopyranosyl-(1 → 4)-β-d-galactopyranosyl-(1 → 4)-β-d-glucopyranoside in 25% and 68% overall yields from commercial lactose, respectively. [Copyright &y& Elsevier]