Section 31
Chapter 30,718

Conversion of GalNAc-beta GlcNAc-beta-OMe into GalNAc-beta - GlcNAc-beta-OMe using human milk alpha-3/4-fucosyltransferase Synthesis of a novel terminal element in glycoprotein glycans

Bergwerff, A.A.; Van Kuik, J.A.; Schiphorst, W.E.C.M.; Koeleman, C.A.M.; Eijnden, D.H.V. Den; Kamerling, J.P.; Vliegenthart, J.F.G.

FEBS (Federation of European Biochemical Societies) Letters 334(1): 133-138


Accession: 030717149

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Incubation of GalNAc-beta(1-4)GlcNAc-beta-OMe with GDP-Fuc in the presence of human milk alpha-3/4-fucosyltransferase resulted in the formation of GalNAc-beta(1-4)(Fuc-alpha(1-3))GlcNAc-beta-OMe. Under conditions that led to complete alpha-3-fucosylation of Gal-beta(1-4)GlcNAc-beta-OEt, GalNAc-beta(14)GlcNAc-beta-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 Gal-beta(1-4)(Fuc-alpha(1-3))GlcNAc-beta-OEt and GalNAc-beta(1-4)(Fuc-alpha(1-3))GlcNAc-beta-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.

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