Synthesis of alpha- and beta-biotinylated T-antigen

被引：5

作者：

Bay, S

BerthierVergnes, O

Cantacuzene, D

机构：

[1] INST PASTEUR, UNITE CHIM ORGAN, DEPT BIOCHIM & GENET MOL, F-75724 PARIS 15, FRANCE

[2] HOP EDOUARD HERRIOT, INSERM, U346, F-69437 LYON 03, FRANCE

来源：

CARBOHYDRATE RESEARCH | 1997年 / 298卷 / 03期

关键词：

T-antigen; chemoenzymatic synthesis; alpha- and beta-biotinylated T-antigen; stereoselective synthesis; aminohexanol as a spacer arm; aminohexanol Schiff base;

D O I：

10.1016/S0008-6215(96)00309-6

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：

The T-antigen [beta-D-Gal-(1 --> 3)-D-GalNAc] has been linked to biotin through a C-6 spacer arm for the detection of a specific 'T-antigen-lectin' complex at the surface and/or on the migration pathway of melanoma cells. When 4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha- or -beta-D-galactopyranosyl halides were treated with N-benzyloxycarbonyl or N-fluorenylmethoxycarbonyl protected aminohexanols (used as the spacer arm), unusual stereoselectivities were observed for the synthesis of the alpha and beta anomers. The synthesis of the alpha anomer could only be achieved, in reasonable yields, with the Schiff base of aminohexanol. (C) 1997 Elsevier Science Ltd.

引用

页码：153 / 161

页数：9

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[11] ENZYMATIC-SYNTHESIS OF SELECTIVELY PROTECTED GLYCALS [J].