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. 1975 Oct;2(10):1727–1736. doi: 10.1093/nar/2.10.1727

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

R von Tigerstrom, P Jahnke, M Smith
PMCID: PMC343540  PMID: 171626

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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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Agarwal K. L., Yamazaki A., Cashion P. J., Khorana H. G. Chemical synthesis of polynucleotides. Angew Chem Int Ed Engl. 1972 Jun;11(6):451–459. doi: 10.1002/anie.197204511. [DOI] [PubMed] [Google Scholar]
  2. Borden R. K., Smith M. Nucleotide synthesis. 3. Preparation of nucleoside-3',5' cyclic phosphates in strong base. J Org Chem. 1966 Oct;31(10):3247–3253. doi: 10.1021/jo01348a035. [DOI] [PubMed] [Google Scholar]
  3. Borden R. K., Smith M. Nucleotide synthesis. II. Nucleotide p-nitrophenyl and 2,4-dinitrophenyl esters. J Org Chem. 1966 Oct;31(10):3241–3246. doi: 10.1021/jo01348a034. [DOI] [PubMed] [Google Scholar]
  4. Nagyvary J., Chladek S., Roe J. The synthesis of 5' thioanalogs of polydeoxyribonucleotides. Biochem Biophys Res Commun. 1970 Jun 5;39(5):878–882. doi: 10.1016/0006-291x(70)90405-5. [DOI] [PubMed] [Google Scholar]
  5. Nagyvary J., Nagpal K. L. Oligothymidylates: formation by thermal condensation of O 2 ,5'-cyclothymidine 3'-phosphate. Science. 1972 Jul 21;177(4045):272–274. doi: 10.1126/science.177.4045.272. [DOI] [PubMed] [Google Scholar]
  6. Von Tigerstrom R., Smith M. Oligodeoxyribonucleotides: chemical synthesis in anhydrous base. Science. 1970 Feb 27;167(3922):1266–1268. doi: 10.1126/science.167.3922.1266. [DOI] [PubMed] [Google Scholar]
  7. von Tigerstrom R. G., Smith M. Preparation of the 2,4-dinitrophenyl esters of thymidine 3'-and thymidine 5'-phosphate and their use as substrates fof phosphodiesterases. Biochemistry. 1969 Jul;8(7):3067–3070. doi: 10.1021/bi00835a056. [DOI] [PubMed] [Google Scholar]

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