Literature DB >> 23050987

Automated solid-phase synthesis of RNA oligonucleotides containing a nonbridging phosphorodithioate linkage via phosphorothioamidites.

Nan-Sheng Li1, John K Frederiksen, Joseph A Piccirilli.   

Abstract

This work describes a general method for the synthesis of oligoribonucleotides containing a site-specific nonbridging phosphorodithioate linkage via automated solid-phase synthesis using 5'-O-DMTr-2'-O-TBS-ribonucleoside 3'-N,N-dimethyl-S-(2,4-dichlorobenzyl) phosphorothioamidites (2a-2d). The 3'-phosphorothioamidites (2a-2d) can be conveniently prepared in good yields (86-99%) via a one-pot reaction from the corresponding 5'-O-DMTr-2'-O-TBS-ribonucleosides (1a-1d).

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Year:  2012        PMID： 23050987      PMCID： PMC3500914          DOI： 10.1021/jo301834p

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


  23 in total

1.  Small interfering RNAs containing full 2'-O-methylribonucleotide-modified sense strands display Argonaute2/eIF2C2-dependent activity.

Authors:  Bryan A Kraynack; Brenda F Baker
Journal:  RNA       Date:  2005-11-21       Impact factor: 4.942

2.  Metal-ion rescue revisited: biochemical detection of site-bound metal ions important for RNA folding.

Authors:  John K Frederiksen; Nan-Sheng Li; Rhiju Das; Daniel Herschlag; Joseph A Piccirilli
Journal:  RNA       Date:  2012-04-26       Impact factor: 4.942

Review 3.  Nucleoside phosphorothioates.

Authors:  F Eckstein
Journal:  Annu Rev Biochem       Date:  1985       Impact factor: 23.643

4.  Absolute configuration of the diastereomers of adenosine 5'-O-(1-thiotriphosphate): consequences for the stereochemistry of polymerization by DNA-dependent RNA polymerase from Escherichia coli.

Authors:  P M Burgers; F Eckstein
Journal:  Proc Natl Acad Sci U S A       Date:  1978-10       Impact factor: 11.205

5.  Phosphorothioate-stimulated uptake of short interfering RNA by human cells.

Authors:  Marita Overhoff; Georg Sczakiel
Journal:  EMBO Rep       Date:  2005-12       Impact factor: 8.807

6.  Synthesis and characterization of a substrate for T4 endonuclease V containing a phosphorodithioate linkage at the thymine dimer site.

Authors:  T Murata; S Iwai; E Ohtsuka
Journal:  Nucleic Acids Res       Date:  1990-12-25       Impact factor: 16.971

7.  Site-specific DNA transesterification catalyzed by a restriction enzyme.

Authors:  Giedrius Sasnauskas; Bernard A Connolly; Stephen E Halford; Virginijus Siksnys
Journal:  Proc Natl Acad Sci U S A       Date:  2007-01-31       Impact factor: 11.205

8.  Gene silencing activity of siRNA molecules containing phosphorodithioate substitutions.

Authors:  Xianbin Yang; Malgorzata Sierant; Magdalena Janicka; Lukasz Peczek; Carlos Martinez; Tom Hassell; Na Li; Xin Li; Tianzhi Wang; Barbara Nawrot
Journal:  ACS Chem Biol       Date:  2012-04-26       Impact factor: 5.100

9.  A new metal ion interaction in the Tetrahymena ribozyme reaction revealed by double sulfur substitution.

Authors:  A Yoshida; S Sun; J A Piccirilli
Journal:  Nat Struct Biol       Date:  1999-04

10.  Mechanisms of single-stranded phosphorothioate modified antisense oligonucleotide accumulation in hepatocytes.

Authors:  Erich Koller; Thomas M Vincent; Alfred Chappell; Soma De; Muthiah Manoharan; C Frank Bennett
Journal:  Nucleic Acids Res       Date:  2011-02-23       Impact factor: 16.971
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  2 in total

1.  Solid-Phase Synthesis of RNA Analogs Containing Phosphorodithioate Linkages.

Authors:  Xianbin Yang
Journal:  Curr Protoc Nucleic Acid Chem       Date:  2017-09-18

2.  Investigating discovery strategies and pharmacological properties of stereodefined phosphorodithioate LNA gapmers.

Authors:  Jörg Duschmalé; Adrian Schäublin; Erik Funder; Steffen Schmidt; Łukasz J Kiełpiński; Helle Nymark; Klaus Jensen; Troels Koch; Martina Duschmalé; Erich Koller; Marianne Ravn Møller; Simone Schadt; Christophe Husser; Andreas Brink; Sabine Sewing; Tanja Minz; Jesper Wengel; Konrad Bleicher; Meiling Li
Journal:  Mol Ther Nucleic Acids       Date:  2022-06-22       Impact factor: 10.183
  2 in total

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