Literature DB >> 171626

The synthesis of the internucleotide (phosphodiester) bond by a base-catalysed reaction.

R von Tigerstrom, P Jahnke, M Smith.   

Abstract

Potassium tert-butoxide in hexamethyl phosphoramide and dimethyl formamide provides an excellent catalyst for the reaction of a 3'-hydroxyl or a 5'-hydroxyl group of a nucleoside with an appropriate nucleoside phosphorofluoridate to yield the dinucleoside phosphate. This paper describes the experiments leading to the development of this reaction together with the synthesis of thymidylyl-(5' leads to 3')-thymidine (dT-dT).

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Year:  1975        PMID: 171626      PMCID: PMC343540          DOI: 10.1093/nar/2.10.1727

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


  7 in total

1.  Preparation of the 2,4-dinitrophenyl esters of thymidine 3'-and thymidine 5'-phosphate and their use as substrates fof phosphodiesterases.

Authors:  R G von Tigerstrom; M Smith
Journal:  Biochemistry       Date:  1969-07       Impact factor: 3.162

2.  The synthesis of 5' thioanalogs of polydeoxyribonucleotides.

Authors:  J Nagyvary; S Chladek; J Roe
Journal:  Biochem Biophys Res Commun       Date:  1970-06-05       Impact factor: 3.575

3.  Chemical synthesis of polynucleotides.

Authors:  K L Agarwal; A Yamazaki; P J Cashion; H G Khorana
Journal:  Angew Chem Int Ed Engl       Date:  1972-06       Impact factor: 15.336

4.  Nucleotide synthesis. 3. Preparation of nucleoside-3',5' cyclic phosphates in strong base.

Authors:  R K Borden; M Smith
Journal:  J Org Chem       Date:  1966-10       Impact factor: 4.354

5.  Oligothymidylates: formation by thermal condensation of O 2 ,5'-cyclothymidine 3'-phosphate.

Authors:  J Nagyvary; K L Nagpal
Journal:  Science       Date:  1972-07-21       Impact factor: 47.728

6.  Oligodeoxyribonucleotides: chemical synthesis in anhydrous base.

Authors:  R Von Tigerstrom; M Smith
Journal:  Science       Date:  1970-02-27       Impact factor: 47.728

7.  Nucleotide synthesis. II. Nucleotide p-nitrophenyl and 2,4-dinitrophenyl esters.

Authors:  R K Borden; M Smith
Journal:  J Org Chem       Date:  1966-10       Impact factor: 4.354

  7 in total

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