Literature DB >> 3480505

An approach to the stereoselective synthesis of Sp-dinucleoside phosphorothioates using phosphotriester chemistry.

R Cosstick1, D M Williams.   

Abstract

An approach to the stereoselective synthesis of Sp- dinucleoside phosphorothioates has been investigated which utilizes phosphotriester chemistry. The stereoselectivity of internucleotide bond formation between N4-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-(S2-cyano-e thyl) phosphorothioate (3) and 3'-O-acetylthymidine has been studied using either mesitylenesulphonyl-5-(pyridin-2-yl)tetrazole (MSPy) or 1-mesitylenesulphonyl-3-nitro-1,2,4-triazole (MSNT) as the activating agent. The removal of the cyanoethyl group from the protected dinucleoside phosphorothioate has been studied, and conditions are reported which provide rapid deprotection without concomittant desulphurisation.

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Year:  1987        PMID： 3480505      PMCID： PMC306540          DOI： 10.1093/nar/15.23.9921

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN： 0305-1048            Impact factor:   16.971


  19 in total

1.  A rapid and convenient synthesis of poly-thymidylic acid by the modified triester approach.

Authors:  A K Sood; S A Narang
Journal:  Nucleic Acids Res       Date:  1977-08       Impact factor: 16.971

2.  Rapid synthesis of oligodeoxyribonucleotides. V. Further studies in solid phase synthesis of oligodeoxyribonucleotides through phosphotriester intermediates.

Authors:  M J Gait; S G Popov; M Singh; R C Titmas
Journal:  Nucleic Acids Symp Ser       Date:  1980

3.  Protected deoxyribonucleoside-3' aryl phosphodiesters as key intermediates in polynucleotide synthesis. Construction of an icosanucleotide analogous to the sequence at the ends of Rous sarcoma virus 35S RNA.

Authors:  G R Gough; C K Singleton; H L Weith; P T Gilham
Journal:  Nucleic Acids Res       Date:  1979-04       Impact factor: 16.971

4.  Chiral phosphorothioate analogues of B-DNA. The crystal structure of Rp-d[Gp(S)CpGp(S)CpGp(S)C].

Authors:  W B Cruse; S A Salisbury; T Brown; R Cosstick; F Eckstein; O Kennard
Journal:  J Mol Biol       Date:  1986-12-20       Impact factor: 5.469

5.  A study of the mechanism of T4 DNA polymerase with diastereomeric phosphorothioate analogues of deoxyadenosine triphosphate.

Authors:  P J Romaniuk; F Eckstein
Journal:  J Biol Chem       Date:  1982-07-10       Impact factor: 5.157

6.  Synthesis of d(GC) and d(CG) octamers containing alternating phosphorothioate linkages: effect of the phosphorothioate group on the B-Z transition.

Authors:  R Cosstick; F Eckstein
Journal:  Biochemistry       Date:  1985-07-02       Impact factor: 3.162

7.  Phosphorothioate-modified oligodeoxyribonucleotides. III. NMR and UV spectroscopic studies of the Rp-Rp, Sp-Sp, and Rp-Sp duplexes, [d(GGSAATTCC)]2, derived from diastereomeric O-ethyl phosphorothioates.

Authors:  L A LaPlanche; T L James; C Powell; W D Wilson; B Uznanski; W J Stec; M F Summers; G Zon
Journal:  Nucleic Acids Res       Date:  1986-11-25       Impact factor: 16.971

8.  A new condensing reagent, 1-(2,4,6-triisopropylbenzenesulfonyl)-5-(pyridin-2-yl)tetrazolide and its use in the synthesis of lambda cro binding heptadecanucleotide on a polymer support.

Authors:  E Ohtsuka; Z Tozuka; S Iwai; M Ikehara
Journal:  Nucleic Acids Res       Date:  1982-10-25       Impact factor: 16.971

9.  Polymer supported synthesis of oligonucleotides by a phosphotriester method.

Authors:  R Belagaje; C K Brush
Journal:  Nucleic Acids Res       Date:  1982-10-25       Impact factor: 16.971

10.  Rapid synthesis of oligodeoxyribonucleotides VI. Efficient, mechanised synthesis of heptadecadeoxyribonucleotides by an improved solid phase phosphotriester route.

Authors:  M L Duckworth; M J Gait; P Goelet; G F Hong; M Singh; R C Titmas
Journal:  Nucleic Acids Res       Date:  1981-04-10       Impact factor: 16.971
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  3 in total

1.  Novel route to oligo(deoxyribonucleoside phosphorothioates). Stereocontrolled synthesis of P-chiral oligo(deoxyribonucleoside phosphorothioates).

Authors:  W J Stec; A Grajkowski; M Koziolkiewicz; B Uznanski
Journal:  Nucleic Acids Res       Date:  1991-11-11       Impact factor: 16.971

2.  Solid phase synthesis of oligodeoxyribonucleoside phosphorodithioates from thiophosphoramidites.

Authors:  K Bjergårde; O Dahl
Journal:  Nucleic Acids Res       Date:  1991-11-11       Impact factor: 16.971

3.  Single base extension (SBE) with proofreading polymerases and phosphorothioate primers: improved fidelity in single-substrate assays.

Authors:  Daniel Di Giusto; Garry C King
Journal:  Nucleic Acids Res       Date:  2003-02-01       Impact factor: 16.971
  3 in total

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