Chemoenzymatic synthesis of a trimeric ganglioside GM(3) analogue

被引:11
作者
Earle, MA
Manku, S
Hultin, PG
Li, H
Palcic, MM
机构
[1] UNIV MANITOBA,DEPT CHEM,WINNIPEG,MB R3T 2N2,CANADA
[2] UNIV ALBERTA,DEPT CHEM,EDMONTON,AB T6G 2G2,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
ganglioside analogue; melanoma antigen; multivalent; alpha-(2->3)-sialyltransferase;
D O I
10.1016/S0008-6215(97)00085-2
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
引用
收藏
页码:1 / 4
页数:4
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