A trimeric beta-lactosyl cluster based on 2-nitro-2-(hydroxymethyl)propane-1,3-diol was prepared using the trichloroacetimidate method. Kinetic studies showed that this cluster was an effective acceptor for rat-liver alpha-(2 --> 3)-sialyltransferase. Its K-M was comparable to those for monomeric lactose and N-acetyllactosamine accepters, and its V-max was 1% of that measured for the LacNAc acceptor. Preparative-scale sialylation using this enzyme afforded a trimeric cluster of the ganglioside GM(3) oligosaccharide in good yield. The NMR spectra of the trimeric GM(3) analogue suggest that the oligosaccharide conformation is not significantly perturbed by this level of clustering. (C) 1997 Elsevier Science Ltd.
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NAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPANNAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN
AOI, K
ITOH, K
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NAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPANNAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN
ITOH, K
OKADA, M
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NAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPANNAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN
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NAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPANNAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN
AOI, K
ITOH, K
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NAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPANNAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN
ITOH, K
OKADA, M
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NAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPANNAGOYA UNIV, FAC AGR SCI, DEPT APPL BIOL SCI, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN