PMID: 7541136Jun 20, 1995Paper

Oligonucleotide N3'-->P5' phosphoramidates

Proceedings of the National Academy of Sciences of the United States of America
S M GryaznovW D Wilson

Abstract

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.

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Citations

Oct 6, 2000·Archives of Biochemistry and Biophysics·L Lacroix, J L Mergny
Dec 31, 1997·Biochemical Pharmacology·C F Bennett
Jun 8, 2002·Journal of Molecular Biology·Nilesh K Banavali, Alexander D MacKerell
Oct 8, 1998·Advances in Enzyme Regulation·M Egli
May 12, 2000·Biochimica Et Biophysica Acta·D PraseuthC Hélène
May 12, 2000·Biochimica Et Biophysica Acta·S M Gryaznov
Jan 1, 1996·Biochimie·J J ToulméE Brossalina
Jun 1, 1996·Current Opinion in Structural Biology·D H Turner
Jun 1, 1996·Current Opinion in Structural Biology·J S SunC Hélène
Oct 9, 2013·Proceedings of the National Academy of Sciences of the United States of America·Shenglong ZhangJack W Szostak
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Dec 25, 2007·Oligonucleotides·Zhaoyang YeRam I Mahato
Aug 1, 1996·Nucleic Acids Research·R G Schultz, S M Gryaznov
Apr 15, 1996·Nucleic Acids Research·S GryaznovB Calabretta
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Feb 15, 1997·Nucleic Acids Research·D BarskyS M Gryaznov
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