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Volumn 38, Issue 11, 1997, Pages 2007-2010

9-fluorenemethyl H-phosphonothioate, a versatile reagent for the preparation of H-phosphonothioate, phosphorothioate, and phosphorodithioate monoesters

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORODITHIOIC ACID DERIVATIVE; PHOSPHOROTHIOIC ACID DERIVATIVE; REAGENT;

EID: 0031575738     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00218-9     Document Type: Article
Times cited : (15)

References (27)
  • 1
    • 0003082218 scopus 로고
    • Phosphorothioate oligodeoxynucleotide analogues
    • J. S. Cohen, Ed.; The Macmillan Press Ltd.: New York
    • 1. Stein, C. A.; Cohen, J. S. Phosphorothioate oligodeoxynucleotide analogues. In Oligodeoxynucleotides-Antisense Inhibitors of Gene Expression; J. S. Cohen, Ed.; The Macmillan Press Ltd.: New York, 1989; Vol. 12; pp. 97-117.
    • (1989) Oligodeoxynucleotides-antisense Inhibitors of Gene Expression , vol.12 , pp. 97-117
    • Stein, C.A.1    Cohen, J.S.2
  • 13
    • 0029909524 scopus 로고    scopus 로고
    • 13. After this work was completed, 9-fluorenemethyl H-phosphonothioate has been advocated by Caruthers et al. as a useful reagent for the introduction of the 5′-terminal phosphorodithioate function to oligonucleotides (see, Seeberger, P. H.; Jorgensen, P. N.; Bankaitisdavis, D. M.; Beaton, G.; Caruthers, M. H. J. Am. Chem. Soc. 1996, 118, 9562-9566). The reported preparation of the reagent was, however, lengthy (a multi-step synthesis) and required several purification steps of the final product.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9562-9566
    • Seeberger, P.H.1    Jorgensen, P.N.2    Bankaitisdavis, D.M.3    Beaton, G.4    Caruthers, M.H.5
  • 16
    • 84920296038 scopus 로고    scopus 로고
    • note
    • HP = 605.9 Hz, H-P).
  • 17
    • 84920296037 scopus 로고    scopus 로고
    • note
    • 31P NMR spectroscopy.
  • 18
    • 84920296036 scopus 로고    scopus 로고
    • For the purpose of the present studies all reactions involving 5 were carried out on the isolated compound
    • 18. For the purpose of the present studies all reactions involving 5 were carried out on the isolated compound.
  • 19
    • 84920296035 scopus 로고    scopus 로고
    • note
    • 31P NMR) with an authentic sample obtained on a different way.
  • 20
    • 84920296034 scopus 로고    scopus 로고
    • note
    • 4OH, 85 : 10 : 5, v/v/v).
  • 21
    • 84920296033 scopus 로고    scopus 로고
    • In pyridine, apparently due to extended time of the reaction, the formation of 8a was accompanied by side products, which most likely resulted from the occurrence of the ligand exchange process in 5 under the reaction conditions
    • 21. In pyridine, apparently due to extended time of the reaction, the formation of 8a was accompanied by side products, which most likely resulted from the occurrence of the ligand exchange process in 5 under the reaction conditions.
  • 22
    • 84920296032 scopus 로고    scopus 로고
    • 31P NMR spectroscopy, and TLC analysis
    • 31P NMR spectroscopy, and TLC analysis.
  • 23
    • 84920296031 scopus 로고    scopus 로고
    • After removing the excess of ammonia and pyridine, the amount of side products considerably increased, indicating that the degradation of 8b also occurred during work-up (i.e. during concentration of the reaction mixture)
    • 23. After removing the excess of ammonia and pyridine, the amount of side products considerably increased, indicating that the degradation of 8b also occurred during work-up (i.e. during concentration of the reaction mixture).
  • 27
    • 84920296030 scopus 로고    scopus 로고
    • note
    • 31P NMR spectroscopy, and by TLC analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.