Seven-Membered Ring Nucleoside Analogues: Stereoselective Synthesis and Studies on Their Conformational Properties

被引：10

作者：

Habibian, Maryam ^{[1
]}

Martinez-Montero, Saul ^{[1
]}

Portella, Guillem ^{[2
]}

Chua, Zhijie ^{[1
]}

Bohle, D. Scott ^{[1
]}

Orozco, Modesto ^{[3
,4
]}

Damha, Masad J. ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada

[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[3] Inst Res Biomed, Joint BSC CRG IRB Programme Computat Biol, Barcelona 08028, Spain

[4] Univ Barcelona, Fac Biol, Dept Bioquim & Biol Mol, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 21期

基金：

加拿大自然科学与工程研究理事会; 欧洲研究理事会;

关键词：

HEXOSE-NUCLEIC-ACIDS; OXEPANE; OLIGONUCLEOTIDES; DISCRIMINATE; NUCLEOTIDES; EXPANSION; PENTOSE; DNA;

D O I：

10.1021/acs.orglett.5b02769

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a novel series of seven-membered ring nucleoside analogues as candidates for biological screening and gene silencing applications is described. The key step in the synthetic approach is a stereoselective synthesis of an epoxide that is used as a common synthetic intermediate to prepare functionalized oxepane nucleoside derivatives. The conformational landscape and preferred ring-puckering of selected oxepane nucleosides was also studied by NMR, X-ray crystallography, and quantum mechanical calculations.

引用

页码：5416 / 5419

页数：4

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