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. 1989 Nov 11;17(21):8581–8593. doi: 10.1093/nar/17.21.8581

Reinvestigation of deoxyribonucleoside phosphorothioites: synthesis and properties of deoxyribonucleoside-3' dimethyl phosphites.

H Nagai 1, T Fujiwara 1, M Fujii 1, M Sekine 1, T Hata 1
PMCID: PMC335029  PMID: 2587213

Abstract

Further investigation of the synthesis of deoxyribonucleoside-3' (t-butyl) O-(2-cyanoethyl) phosphorothioites as monomer building units for the phosphorothioite approach has led us to conclude that internucleotidic bond formation proceeded via bis(deoxyribonucleoside-3') (2-cyanoethyl) phosphite intermediates, which proved to be activated by iodine, rather than the mechanism previously reported. In connection with this study, deoxyribonucleoside-3' dimethyl phosphites were synthesized and detailed properties of them are also described.

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Selected References

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

  1. Daub G. W., van Tamelen E. E. Synthesis of oligoribonucleotides based on the facile cleavage of methyl phosphotriester intermediates. J Am Chem Soc. 1977 May 11;99(10):3526–3528. doi: 10.1021/ja00452a069. [DOI] [PubMed] [Google Scholar]
  2. SLOANE di NEW-YORK L'asse a cerniera (hinge axis), secondo Mac Collum. Riv Ital Stomatol. 1950 Apr;5(4):457–465. [PubMed] [Google Scholar]
  3. Sinha N. D., Biernat J., McManus J., Köster H. Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucleic Acids Res. 1984 Jun 11;12(11):4539–4557. doi: 10.1093/nar/12.11.4539. [DOI] [PMC free article] [PubMed] [Google Scholar]

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