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Volumn 63, Issue 26, 1998, Pages 10035-10039

Synthesis of 2'-amino-LNA: A novel conformationally restricted high- affinity oligonucleotide analogue with a handle

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; LOCKED NUCLEIC ACID; NUCLEIC ACID; OLIGONUCLEOTIDE; UNCLASSIFIED DRUG;

EID: 0032567380     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9814445     Document Type: Article
Times cited : (137)

References (41)
  • 3
    • 0028019410 scopus 로고
    • (c) Wagner, R. W. Nature 1994, 372, 333.
    • (1994) Nature , vol.372 , pp. 333
    • Wagner, R.W.1
  • 21
    • 20644459550 scopus 로고    scopus 로고
    • note
    • We have defined LNA as ONs containing one or more 2′-O,4′-C-methylene bicyclic ribonucleoside LNA monomers. 2′-Amino-LNA is defined as an ON containing one or more 2′-N,4′-C-methylene bicyclic 2′-amino-LNA monomers (possibly N-derivatized, e.g., N-methylated to give 2′-methylamino-LNA).
  • 22
    • 0030862285 scopus 로고    scopus 로고
    • The LNA nucleosides containing uracil and cytosine nucleobases have been synthesized independently by a linear approach: Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735. Oligomers containing these pyrimidine bases have recently been reported: Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8735
    • Obika, S.1    Nanbu, D.2    Hari, Y.3    Morio, K.4    In, Y.5    Ishida, T.6    Imanishi, T.7
  • 23
    • 0032560835 scopus 로고    scopus 로고
    • The LNA nucleosides containing uracil and cytosine nucleobases have been synthesized independently by a linear approach: Obika, S.; Nanbu, D.; Hari, Y.; Morio, K.; In, Y.; Ishida, T.; Imanishi, T. Tetrahedron Lett. 1997, 38, 8735. Oligomers containing these pyrimidine bases have recently been reported: Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Morio, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5401
    • Obika, S.1    Nanbu, D.2    Hari, Y.3    Andoh, J.4    Morio, K.5    Doi, T.6    Imanishi, T.7
  • 24
    • 20644469090 scopus 로고    scopus 로고
    • note
    • Preorganization of LNA nucleosides into a 3′-endo type conformation has been shown by X-ray crystallography (ref 5) and by NMR studies (ref 3).
  • 25
    • 0031900834 scopus 로고    scopus 로고
    • The importance of hydration on duplex stability has been reported for conformationally restricted N3′-P5′-phosphoramidate DNA: Egli, M. Antisense Nucleic Acids Drug Dev. 1998, 8, 123.
    • (1998) Antisense Nucleic Acids Drug Dev. , vol.8 , pp. 123
    • Egli, M.1
  • 26
    • 20644445253 scopus 로고    scopus 로고
    • in press
    • Preliminary thermodynamic analysis of binding between a fully modified LNA and complementary DNA has indicated a significant enthalpic advantage compared to the corresponding unmodified control: Koshkin, A. A.; Nielsen, P.; Meldgaard, M.; Rajwanshi, V. K.; Singh, S. K.; Wengel, J. J. Am. Chem. Soc., in press. A favorable entropy term has been reported for a duplex between a partly modified LNA and RNA (ref 5).
    • J. Am. Chem. Soc.
    • Koshkin, A.A.1    Nielsen, P.2    Meldgaard, M.3    Rajwanshi, V.K.4    Singh, S.K.5    Wengel, J.6
  • 36
    • 0000484783 scopus 로고    scopus 로고
    • In a communication, we have reported synthesis of the unprotected 2́-amino-LNA and 2́-thio-LNA nucleosides: Singh, S. K.; Kumar, R.; Wengel, J. J. Org. Chem. 1998, 63, 6078.
    • (1998) J. Org. Chem. , vol.63 , pp. 6078
    • Singh, S.K.1    Kumar, R.2    Wengel, J.3
  • 37
    • 20644471217 scopus 로고    scopus 로고
    • note
    • 3, 62.9 MHz, selected signals) 172.0, 159.1, 21.7. No trace of bicyclonucleoside 3 was detected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.