Abstract
n-Alkyl alpha- and beta-D-glucopyranosides with different alkyl chain lengths (Glc-O-CxH2x+1) and n-octyl beta-D-thioglucopyranoside (Glc-S-C8H17) were synthesized, and used as acceptors for galactosyltransferases from rat liver Golgi vesicles. Only the beta-anomers were galactosylated and at constant substrate concentration, the reaction rates reached a maximum for medium alkyl chain lengths (C6, C8 and C10). Apparent Km and Vmax values decreased with increasing alkyl chain length. The reaction products were identified as n-alkyl beta-lactosides by means of thin layer chromatography, fast atom bombardment mass spectrometry and 1H-NMR spectroscopy. Competition experiments showed that UDP-Gal: N-acetylglucosamine beta 1-4-galactosyltransferase (EC 2.4.1.38) and not UDP-Gal: glucosylceramide beta 1-4-galactosyltransferase (lactosylceramide synthase, GalT-2) was responsible for the galactosylation of alkyl glucosides.
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