Enzymatic synthesis of two lacto-N-neohexaose-related Lewis x heptasaccharides and their separation by chromatography on

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Abstract
Radiolabelled lacto-N-neohexaosc was fucosylated with partially purified α(l,3)fucosyltransferase{s) from human milk. Structural analysis of the monofucosylated products obtained at an early stage of the reaction revealed that both distal branches of the acceptor had reacted equally well, generating Lewis x determinants, while the reducing end glucose had not reacted. The two isomeric Lewis x glycans were readily separated from each other by chromatography on immobilized wheat germ agglutinin (WGA), because α(l,3)fucosylation of the (1→6)-linked branch of lactoWV-neohexaose was associated with a dramatic loss of WGA affinity. The fucosylation mixture of lactoN-neohexaose also contained a difucosylderivative that carried Lewis x determinants at both distal branches. Attempted re-fucosylation of this octasaccharide failed to transfer fucose to the glucose unit.

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