Skip to main content
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1986 Mar 25;14(6):2699–2706. doi: 10.1093/nar/14.6.2699

The role of metaphosphate in the activation of the nucleotide by TPS and DCC in the oligonucleotide synthesis.

Y Wang, Z W Yang, Q W Wang, Y Z Xu, X Y Liu, J F Xu, C H Chen
PMCID: PMC339692  PMID: 3754328

Abstract

The course of the activation of 3'-acetylthymidine 5'-phosphate by TPS and DCC were followed up by 31P FT nmr. The fact that the "metaphosphate" (delta-5.1) first becomes detectable only at later stage of the activation and does coexist with pyrophosphate and triphosphate suggests that the pyridinium derivative of "metaphosphate" is most probably not directly formed from the hypothetical mixed anhydride or active "pseudourea" right at the beginning of the reaction of pdTac with TPS or DCC, but rather formed at later stage of the activation reaction from the degradation of the pyro- and triphosphates by the activating agent. The mixed anhydride or the active "pseudourea" is most possibly the active key intermediate.

Full text

PDF
2699

Selected References

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

  1. Eckstein F., Rizk I. Synthese von Oligodesoxynucleotiden über Phosphorsäure-triester. Chem Ber. 1969;102(7):2362–2377. doi: 10.1002/cber.19691020724. [DOI] [PubMed] [Google Scholar]
  2. Katagiri N., Itakura K., Narang S. A. The use of arylsulfonyltriazoles for the synthesis of oligonucleotides by the triester approach. J Am Chem Soc. 1975 Dec 10;97(25):7332–7337. doi: 10.1021/ja00858a021. [DOI] [PubMed] [Google Scholar]
  3. Knorre D. G., Zarytova V. F. The mechanism of the chemical synthesis of oligonucleotides and its synthetic consequences. Nucleic Acids Res. 1976 Oct;3(10):2709–2729. doi: 10.1093/nar/3.10.2709. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Todd S. A. SOME ASPECTS OF PHOSPHATE CHEMISTRY. Proc Natl Acad Sci U S A. 1959 Sep;45(9):1389–1397. doi: 10.1073/pnas.45.9.1389. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES