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Conversion of GalNAcβ(1–4)GlcNAcβ-OMe into GalNAcβ(1–4)-[Fucα(1–3)]GlcNAcβ-OMe using human milk α34-fucosyltransferase synthesis of a novel terminal element in glycoprotein glycans

By Aldert A. Bergwerff, J.Albert van Kuik, Wietske E.C.M. Schiphorst, Carolien A.M. Koeleman, Dirk H. van den Eijnden, Johannis P. Kamerling and Johannes F.G. Vliegenthart

Abstract

AbstractIncubation of GalNAcβ(1–4)GlcNAcβ-OMe with GDP-Fuc in the presence of human milk α34-fucosyltransferase resulted in the formation of GalNAcβ(1–4)[Fucα(1–3)]GlcNAcβ-OMe. Under conditions that led to complete α3-fucosylation of Galβ(1–4)GlcNAcβ-OEt, GalNAcβ(1–4)GlcNAcβ-OMe was fucosylated for more than 85%. For the identification of the isolated fucosylated products one- and two- dimensional 1H-NMR spectroscopy was applied. In vacuo molecular dynamics simulations of Galβ(1–4)[Fucα(1–3)]GlcNAcβ-OEt and GalNAcβ(1–4)[Fucα(1–3)]GlcNAcβ-OMe using the CHARMm based force field CHEAT, demonstrated only small differences between the conformations of these compounds. This illustrates the minor conformational influence of the substituent at C-2′, i.e. a hydroxyl function versus a N-acetyl group

Publisher: Published by Elsevier B.V.
Year: 1993
DOI identifier: 10.1016/0014-5793(93)81698-Y
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