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Volumn 125, Issue 11 SPEC. ISS., 2004, Pages 1745-1756

Analogues of nucleotides and oligonucleotides featuring difluorophosphonate, difluorophosphonothioate and difluorophosphinate functional groups

Author keywords

Antisense strategy; Difluorophosphonate; Difluorophosphonothioate; H difluorophosphinate; Nucleotide analogues

Indexed keywords

KETONE; NUCLEOTIDE; OLIGONUCLEOTIDE; PHOSPHATE; PHOSPHINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHONOACETIC ACID; REAGENT;

EID: 9944225294     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2004.09.028     Document Type: Conference Paper
Times cited : (5)

References (135)
  • 2
    • 9944252875 scopus 로고    scopus 로고
    • note
    • It has been shown that nature use the same principle to down regulate the production of certain proteins. See:
  • 4
    • 9944256155 scopus 로고    scopus 로고
    • note
    • For leading references on the antisense strategy, see:
  • 11
    • 9944258987 scopus 로고    scopus 로고
    • note
    • It has been shown that heteroduplexes between m-RNA and MON may be recognized by RNase H and result in the selective cleavage of the m-RNA strand. See:
  • 18
    • 0001929474 scopus 로고    scopus 로고
    • G. Stix Sci. Am. 297 1998 46 50
    • (1998) Sci. Am. , vol.297 , pp. 46-50
    • Stix, G.1
  • 25
    • 85057633810 scopus 로고    scopus 로고
    • note
    • m values, see reference [3a]
  • 26
    • 9944224214 scopus 로고    scopus 로고
    • note
    • The ground work of Blackbum and McKenna in the early eighties has resulted in the synthesis of a number of analogues encompassing the α,α-difluorophosphonate unit. See for instance:
  • 35
    • 9944229957 scopus 로고    scopus 로고
    • note
    • It has also been suggested that the α-monofluorophosphonates give, at least in some cases, superior results to α,α-difluorination in phosphonate mimics of biological phosphates. See:
  • 42
    • 9944243617 scopus 로고    scopus 로고
    • note
    • Beside this approach and the radical one described in the second part of this paper, other possible solutions to the problem of preparing difluorophosphonates with this particular substitution pattern have been published. See:
  • 78
    • 9944238292 scopus 로고    scopus 로고
    • See reference [12c]
    • See reference [12c]
  • 79
    • 9944265733 scopus 로고    scopus 로고
    • note
    • The crystal structure data of compound 24 have been deposited at the Cambridge Crystallographic Data Centre (deposition number: CCDC 244631).
  • 93
    • 9944244027 scopus 로고    scopus 로고
    • note
    • The suggestion by Shibuya of the possible participation of a phosphonothioyl unit (the result of the longer PS bond, when compared to the PO bond) might be extended to the difluorinated analogue. See:
  • 97
    • 9944236298 scopus 로고    scopus 로고
    • note
    • Yokomatsu has recently described the synthesis of a fully protected 2,3-deoxy-3-phosphonodifluoromethyl nucleoside. See references [14k,m].
  • 98
    • 85057633744 scopus 로고    scopus 로고
    • note
    • 2 center followed by a sigmatropic rearrangement. See reference [14g].
  • 104
    • 9944265015 scopus 로고    scopus 로고
    • note
    • Tedder has discussed the importance of polarity, bond strength and steric effects on the rate of both free radical addition to olefins and free radical substitution. See:
  • 114
    • 0001523773 scopus 로고
    • Some Aspects of H-Phosphonate Chemistry
    • R. Engel Marcel Dekker New York
    • J. Stawinski Some Aspects of H-Phosphonate Chemistry R. Engel Handbook of Organophosphorus Chemistry 1992 Marcel Dekker New York 377 434
    • (1992) Handbook of Organophosphorus Chemistry , pp. 377-434
    • Stawinski, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.