OLIGONUCLEOTIDE N3'-]P5' PHOSPHORAMIDATES

被引：168

作者：

GRYAZNOV, SM ^{[1
]}

LLOYD, DH ^{[1
]}

CHEN, JK ^{[1
]}

SCHULZ, RG ^{[1
]}

DEDIONISIO, LA ^{[1
]}

RATMEYER, L ^{[1
]}

WILSON, WD ^{[1
]}

机构：

[1] GEORGIA STATE UNIV,DEPT CHEM,ATLANTA,GA 30303

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 1995年 / 92卷 / 13期

关键词：

D O I：

10.1073/pnas.92.13.5798

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Synthetic oligonucleotides and their analogs have attracted considerable interest recently, These compounds may lead to highly specific therapeutic agents, as well as to powerful diagnostic tools, Here, we present the synthesis of uniformly modified oligodeoxyribonucleotide N3' --> P5' phosphoramidates containing 3'-NHP(O)(O-)O-5' internucleoside linkages and the study of their hybridization properties, Thermal dissociation experiments show that these compounds form very stable duplexes with single-stranded DNA, RNA, and with themselves following Watson-Crick base pairing, The duplex thermal, stability was enhanced by 2.2-2.6 degrees C per modified linkage compared with phosphodiesters. The structure of complexes formed by phosphoramidates closely resembles that of RNA oligomers and corresponds to an A form, as judged by CD spectroscopy, N3' --> P5' phosphoramidates also form stable triplexes with double-stranded DNA under near-physiological conditions when natural phosphodiesters fail to do so, Physicochemical characteristics of the amidates are similar to those of RNA oligomers, even though they are composed of 2'-deoxyfuranose-based nucleosides.

引用

页码：5798 / 5802

页数：5

共 18 条

[1] SOLID-PHASE SYNTHESIS OF OLIGODEOXYNUCLEOTIDES CONTAINING PHOSPHORAMIDATE INTERNUCLEOTIDE LINKAGES AND THEIR SPECIFIC CHEMICAL CLEAVAGE [J].