Monosaccharide-based water-soluble fluorescent tags

被引：29

作者：

Katritzky, Alan R. ^{[1
]}

Cusido, Janet ^{[1
]}

Narindoshvili, Tamari ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

BIOCONJUGATE CHEMISTRY | 2008年 / 19卷 / 07期

关键词：

D O I：

10.1021/bc8001369

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Monosaccharides are fluorescently labeled under microwave irradiation by N-(coumarin-3-carbonyl)benzotriazole 4. 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose 9 gives 12 (90%), 1,2:5,6-di-O-isopropylidene-D-glucose 10 gives 13 (89%), 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose 11 gives 14 (65%) (all by O-acylation) and 2,3,4,5-tetra- O-pivalOyl-beta-D-galactopyranosylamine 15 gives 16 (60%) (by N-acylation). Similarly, the coumarin-containing activated lysine derivatives 7 and 8 afford the L-lysine-scaffold based coumarin labeled sugars 17, 18a,b, and 19 (67-85%) which, after removal of the diisopropylidene groups, provide water-soluble fluorescent derivatives.

引用

页码：1471 / 1475

页数：5

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