Literature DB >> 11671841

N3'-->P5' Oligodeoxyribonucleotide Phosphoramidates: A New Method of Synthesis Based on a Phosphoramidite Amine-Exchange Reaction.

Jeffrey S. Nelson1, Karen L. Fearon, Mark Q. Nguyen, Sarah N. McCurdy, Jeff E. Frediani, Michael F. Foy, Bernard L. Hirschbein.   

Abstract

A new method for the synthesis of N3'-->P5' phosphoramidate oligodeoxynucleotides is demonstrated. Described herein is the synthesis of the monomers utilized in the phosphoramidite amine-exchange process and the experimental details pertaining to this new mode of chain assembly. The phosphoramidite amine-exchange method generates coupling yields in the 92-95% range per cycle and further enables the synthesis of chimeric phosphoramidate/phosphodiester or phosphoramidate/phosphorothioate oligonucleotides with no instrument modifications.

Entities:  

Year:  1997        PMID： 11671841     DOI： 10.1021/jo970801t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Inhibition of IL-6 in mice by anti-NF-kappaB oligodeoxyribonucleotide N3'-->oligodeoxyribonnucleotide N3' --> P5' phosphoramidates.

Authors:  L Wang; S Gryaznov; M Nerenberg
Journal:  Inflammation       Date:  1999-12       Impact factor: 4.092

2.  Loop-loop interaction of HIV-1 TAR RNA with N3'-->P5' deoxyphosphoramidate aptamers inhibits in vitro Tat-mediated transcription.

Authors:  Fabien Darfeuille; Andrey Arzumanov; Sergei Gryaznov; Michael J Gait; Carmelo Di Primo; Jean-Jacques Toulmé
Journal:  Proc Natl Acad Sci U S A       Date:  2002-07-08       Impact factor: 11.205

3.  DNA polymerase activity on synthetic N3'→P5' phosphoramidate DNA templates.

Authors:  Victor S Lelyveld; Derek K O'Flaherty; Lijun Zhou; Enver Cagri Izgu; Jack W Szostak
Journal:  Nucleic Acids Res       Date:  2019-09-26       Impact factor: 16.971

4.  Targeted inhibition of transcription elongation in cells mediated by triplex-forming oligonucleotides.

Authors:  M Faria; C D Wood; L Perrouault; J S Nelson; A Winter; M R White; C Helene; C Giovannangeli
Journal:  Proc Natl Acad Sci U S A       Date:  2000-04-11       Impact factor: 11.205

5.  RNA mimetics: oligoribonucleotide N3'-->P5' phosphoramidates.

Authors:  S M Gryaznov; H Winter
Journal:  Nucleic Acids Res       Date:  1998-09-15       Impact factor: 16.971

6.  An improved synthesis of oligodeoxynucleotide N3'-->P5' phosphoramidates and their chimera using hindered phosphoramidite monomers and a novel handle for reverse phase purification.

Authors:  K L Fearon; B L Hirschbein; J S Nelson; M F Foy; M Q Nguyen; A Okruszek; S N McCurdy; J E Frediani; L A DeDionisio; A M Raible; E N Cagle; V Boyd
Journal:  Nucleic Acids Res       Date:  1998-08-15       Impact factor: 16.971

7.  NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A-T phosphoramidite building blocks.

Authors:  Boris Schmidtgall; Claudia Höbartner; Christian Ducho
Journal:  Beilstein J Org Chem       Date:  2015-01-13       Impact factor: 2.883

8.  Chemical ligation of oligonucleotides using an electrophilic phosphorothioester.

Authors:  Hideto Maruyama; Ryota Oikawa; Mayu Hayakawa; Shono Takamori; Yasuaki Kimura; Naoko Abe; Genichiro Tsuji; Akira Matsuda; Satoshi Shuto; Yoshihiro Ito; Hiroshi Abe
Journal:  Nucleic Acids Res       Date:  2017-07-07       Impact factor: 16.971
  8 in total

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