Use of phosphorus oxychloride in synthesizing nucleotides and ollgonucleotides

W. S. Mungall, G. L. Greene, P. S. Miller, R. L. Letsinger

Research output: Contribution to journalArticle

Abstract

Procedures are described for phosphorylating protected nucleotides, oligonucleotides and phosphoramidate oligonucleotide derivatives at the 3′-hydroxyl group. The conditions (phosphorylation with phosphorus oxychloride and pyridine in dioxane followed by hydrolysis with aqueous pyridine) are sufficiently mild that base labile (trifluoroacetylamino; β-cyanoethyl phosphotriester) and acid labile (O-monomethoxytrityl; phosphoramidate) functions are retained intact. Application of the technique is illustrated by the synthesis of dpT, dTp, d(CF3CONH)Tp, dTpNTp, and dTpNTpNTp. In addition, the utilization of phosphorus oxychloride in joining thymidine derivatives and dinucleoside phosphotriester blocks via phosphodiester links is described.

Original languageEnglish (US)
Pages (from-to)615-627
Number of pages13
JournalNucleic Acids Research
Volume1
Issue number4
DOIs
StatePublished - Apr 1974
Externally publishedYes

Fingerprint

Phosphorus
Oligonucleotides
Nucleotides
Pyridine
Derivatives
Derivative
Phosphorylation
Joining
Hydroxyl Radical
Thymidine
Hydrolysis
Synthesis
Acids
pyridine
phosphoramidic acid
phosphoryl chloride
1,4-dioxane

ASJC Scopus subject areas

  • Statistics, Probability and Uncertainty
  • Applied Mathematics
  • Health, Toxicology and Mutagenesis
  • Toxicology
  • Genetics(clinical)
  • Genetics

Cite this

Mungall, W. S., Greene, G. L., Miller, P. S., & Letsinger, R. L. (1974). Use of phosphorus oxychloride in synthesizing nucleotides and ollgonucleotides. Nucleic Acids Research, 1(4), 615-627. https://doi.org/10.1093/nar/1.4.615

Use of phosphorus oxychloride in synthesizing nucleotides and ollgonucleotides. / Mungall, W. S.; Greene, G. L.; Miller, P. S.; Letsinger, R. L.

In: Nucleic Acids Research, Vol. 1, No. 4, 04.1974, p. 615-627.

Research output: Contribution to journalArticle

Mungall, WS, Greene, GL, Miller, PS & Letsinger, RL 1974, 'Use of phosphorus oxychloride in synthesizing nucleotides and ollgonucleotides', Nucleic Acids Research, vol. 1, no. 4, pp. 615-627. https://doi.org/10.1093/nar/1.4.615
Mungall, W. S. ; Greene, G. L. ; Miller, P. S. ; Letsinger, R. L. / Use of phosphorus oxychloride in synthesizing nucleotides and ollgonucleotides. In: Nucleic Acids Research. 1974 ; Vol. 1, No. 4. pp. 615-627.
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