Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates by an oxazaphospholidine approach using acid-labile N-protecting groups

被引：13

作者：

Iwamoto, Naoki ^{[1
]}

Oka, Natsuhisa ^{[1
]}

Wada, Takeshi ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Frontier Sci, Dept Med Genome Sci, Kashiwa, Chiba 2778562, Japan

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 33期

关键词：

Stereocontrolled synthesis; Boranophosphate; Oxazaphospholidine approach; H-Phosphonate; SOLID-PHASE SYNTHESIS; BORANE PHOSPHONATE DNA; DINUCLEOSIDE BORANOPHOSPHATES; BORANOPHOSPHOTRIESTER METHOD; OLIGONUCLEOSIDE BORANOPHOSPHATES; STEREOSELECTIVE-SYNTHESIS; PHOSPHOROTHIOATE ANALOGS; CHEMICAL-SYNTHESIS; COMPLEXES; STABILITY;

D O I：

10.1016/j.tetlet.2012.06.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oligodeoxyribonucleoside boranophosphates (PB-ODNs) were synthesized in a stereocontrolled manner via the corresponding H-phosphonates with fully deprotected nucleobases by using diastereopure 2'-deoxyribonucleoside 3'-O-oxazaphospholidine monomers bearing acid-labile protecting groups on the nucleobases. Using the resultant stereodefined PB-ODNs, we demonstrated that the thermal stability of the duplexes of PB-ODNs with complementary oligonucleotides was dependent on the configuration of their phosphorus atoms. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4361 / 4364

页数：4

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