Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chlorosugar

被引：14

作者：

Bag, Subhendu Sekhar ^{[1
]}

Talukdar, Sangita ^{[1
]}

Anjali, S. J. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bioorgan Chem Lab, Gauhati 781039, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 08期

关键词：

Stereoselective; Regioselective; S(N)2 reaction; 2,5-Disubstituted tetrazoles; Tetrazolyl-N2-beta-nucleosides; MEDICINAL CHEMISTRY; TETRAZOLE; GLYCOSYLATION; ANALOGS; OLIGONUCLEOTIDES; NUCLEOTIDES; EQUILIBRIUM; STABILITY; NITRILES; ARYL;

D O I：

10.1016/j.bmcl.2016.02.078

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We are reporting a regioselective and stereoselective route to N2-beta-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The S(N)2 substitution reaction at the anomeric center of Hoffer's chlorosugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at alpha-chlorosugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theoretical (DFT) study. The methodology is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnological and DNA based material science applications. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2044 / 2050

页数：7