메뉴 건너뛰기




Volumn 31, Issue 24, 2003, Pages 7150-7158

The base pairing properties of 8-aza-7-deaza-2′-deoxyisoguanosine and 7-halogenated derivatives in oligonucleotide duplexes with parallel and antiparallel chain orientation

Author keywords

[No Author keywords available]

Indexed keywords

7 BROMO 8 AZA 7 DEAZA 2' DEOXYISOGUANOSINE; 7 IODO 8 AZA 7 DEAZA 2' DEOXYISOGUANOSINE; 8 AZA 7 DEAZA 2' DEOXYISOGUANOSINE; DNA; GUANOSINE DERIVATIVE; HALOGEN; MONOMER; NUCLEOSIDE DERIVATIVE; OLIGODEOXYRIBONUCLEOTIDE; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0346888669     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/gkg926     Document Type: Article
Times cited : (28)

References (30)
  • 1
    • 0002785472 scopus 로고
    • 2′-Deoxyisoguanosine: Synthesis and incorporation into oligodeoxyribonucleotides
    • Seela,F., Gabler,B. and Kazimierczuk,Z. (1993) 2′-Deoxyisoguanosine: synthesis and incorporation into oligodeoxyribonucleotides. Collect. Czech. Chem. Commun., 58, 170-173.
    • (1993) Collect. Czech. Chem. Commun. , vol.58 , pp. 170-173
    • Seela, F.1    Gabler, B.2    Kazimierczuk, Z.3
  • 2
    • 0029911446 scopus 로고    scopus 로고
    • Remarkably stable parallel-stranded oligonucleotides containing 5-methylisocytosine and isoguanine
    • Sugiyama,H., Ikeda,S. and Saito,I. (1996) Remarkably stable parallel-stranded oligonucleotides containing 5-methylisocytosine and isoguanine. J. Am. Chem. Soc., 118, 9994-9995.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9994-9995
    • Sugiyama, H.1    Ikeda, S.2    Saito, I.3
  • 3
    • 0031040441 scopus 로고    scopus 로고
    • Oligonucleotides containing consecutive 2′-deoxyisoguanosine residues: Synthesis, duplexes with parallel chain orientation, and aggregation
    • Seela,F. and Wei,C. (1997) Oligonucleotides containing consecutive 2′-deoxyisoguanosine residues: synthesis, duplexes with parallel chain orientation, and aggregation. Helv. Chim. Acta, 80, 73-85.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 73-85
    • Seela, F.1    Wei, C.2
  • 4
    • 0033618466 scopus 로고    scopus 로고
    • Parallel-stranded oligonucleotide duplexes containing 5-methylisocytosine-guanine and isoguaninecytosine base pairs
    • Seela,F., He,Y. and Wei,C. (1999) Parallel-stranded oligonucleotide duplexes containing 5-methylisocytosine-guanine and isoguaninecytosine base pairs. Tetrahedron, 55, 9481-9500.
    • (1999) Tetrahedron , vol.55 , pp. 9481-9500
    • Seela, F.1    He, Y.2    Wei, C.3
  • 6
    • 0034615181 scopus 로고    scopus 로고
    • The influence of modified purine bases on the stability of parallel DNA
    • Seela,F., Wei,C., Becher,G., Zulauf,M. and Leonard,P. (2000) The influence of modified purine bases on the stability of parallel DNA. Bioorg. Med. Chem. Lett., 10, 289-292.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 289-292
    • Seela, F.1    Wei, C.2    Becher, G.3    Zulauf, M.4    Leonard, P.5
  • 7
    • 0030035948 scopus 로고    scopus 로고
    • Oligodeoxynucleotides containing C-7 propyne analogs of 7-deaza-2′-deoxyguanosine and 7-deaza-2′-deoxyadenosine
    • Buhr,C.A., Wagner,R.W., Grant,D. and Froehler,B.C. (1996) Oligodeoxynucleotides containing C-7 propyne analogs of 7-deaza-2′-deoxyguanosine and 7-deaza-2′-deoxyadenosine. Nucleic Acids Res., 24, 2974-2980.
    • (1996) Nucleic Acids Res. , vol.24 , pp. 2974-2980
    • Buhr, C.A.1    Wagner, R.W.2    Grant, D.3    Froehler, B.C.4
  • 8
    • 0032528042 scopus 로고    scopus 로고
    • Biophysical and antisense properties of oligodeoxynucleotides containing 7-propynyl-, 7-iodo- and 7-cyano-7-deaza-2-amino-2′-deoxyadenosines
    • Balow,G., Mohan,V., Lesnik,E.A., Johnston,J.F., Monia,B.P. and Acevedo,O.L. (1998) Biophysical and antisense properties of oligodeoxynucleotides containing 7-propynyl-, 7-iodo- and 7-cyano-7-deaza-2-amino-2′-deoxyadenosines. Nucleic Acids Res., 26, 3350-3357.
    • (1998) Nucleic Acids Res. , vol.26 , pp. 3350-3357
    • Balow, G.1    Mohan, V.2    Lesnik, E.A.3    Johnston, J.F.4    Monia, B.P.5    Acevedo, O.L.6
  • 9
    • 0029102264 scopus 로고
    • Duplex stabilization of DNA: Oligonucleotides containing 7-substituted 7-deazaadenines
    • Seela,F. and Thomas,H. (1995) Duplex stabilization of DNA: oligonucleotides containing 7-substituted 7-deazaadenines. Helv. Chim. Acta, 78, 94-108.
    • (1995) Helv. Chim. Acta , vol.78 , pp. 94-108
    • Seela, F.1    Thomas, H.2
  • 10
    • 0029812382 scopus 로고    scopus 로고
    • Duplex stability of 7-deazapurine DNA: Oligonucleotides containing 7-bromo- or 7-iodo-7-deazaguanine
    • Ramzaeva,N. and Seela,F. (1996) Duplex stability of 7-deazapurine DNA: oligonucleotides containing 7-bromo- or 7-iodo-7-deazaguanine. Helv. Chim. Acta, 79, 1549-1558.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 1549-1558
    • Ramzaeva, N.1    Seela, F.2
  • 11
    • 20444449794 scopus 로고    scopus 로고
    • Oligonucleotides containing 7- or 8-methyl-7-deazaguanine: Steric requirements of major groove substituents on the DNA structure
    • Seela,F. and Chen,Y. (1996) Oligonucleotides containing 7- or 8-methyl-7-deazaguanine: steric requirements of major groove substituents on the DNA structure. Chem. Commun., 2263-2264.
    • (1996) Chem. Commun. , pp. 2263-2264
    • Seela, F.1    Chen, Y.2
  • 12
    • 0035004756 scopus 로고    scopus 로고
    • Major-groove-halogenated DNA: The effects of bromo and iodo substituents replacing H-C(7) of 8-aza-7-deazapurine-2,6-diamine or H-C(5) of uracil residues
    • Becher,G., He,J. and Seela,F. (2001) Major-groove-halogenated DNA: the effects of bromo and iodo substituents replacing H-C(7) of 8-aza-7-deazapurine-2,6-diamine or H-C(5) of uracil residues. Helv. Chim. Acta, 84, 1048-1065.
    • (2001) Helv. Chim. Acta , vol.84 , pp. 1048-1065
    • Becher, G.1    He, J.2    Seela, F.3
  • 13
    • 0032835007 scopus 로고    scopus 로고
    • Oligonucleotides containing pyrazolo [3,4-d]pyrimidines: The influence of 7-substituted 8-aza-7-deaza-2′-deoxyguanosines on the duplex structure and stability
    • Seela,F. and Becher,G. (1999) Oligonucleotides containing pyrazolo [3,4-d]pyrimidines: the influence of 7-substituted 8-aza-7-deaza-2′-deoxyguanosines on the duplex structure and stability. Helv. Chim. Acta, 82, 1640-1655.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 1640-1655
    • Seela, F.1    Becher, G.2
  • 14
    • 0342422047 scopus 로고    scopus 로고
    • Stabilisation of duplex DNA by 7-halogenated 8-aza-7-deazaguanines
    • Seela,F. and Becher,G. (1998) Stabilisation of duplex DNA by 7-halogenated 8-aza-7-deazaguanines. Chem. Commun., 2017-2018.
    • (1998) Chem. Commun. , pp. 2017-2018
    • Seela, F.1    Becher, G.2
  • 15
    • 0035213433 scopus 로고    scopus 로고
    • Quadruplex and pentaplex self-assemblies of oligonucleotides containing short runs of 8-aza-7-deaza-2′-deoxyisoguanosine or 2′-deoxyisoguanosine
    • Seela,F. and Kröschel,R. (2001) Quadruplex and pentaplex self-assemblies of oligonucleotides containing short runs of 8-aza-7-deaza-2′-deoxyisoguanosine or 2′-deoxyisoguanosine. Bioconjugate Chem., 12, 1043-1050.
    • (2001) Bioconjugate Chem. , vol.12 , pp. 1043-1050
    • Seela, F.1    Kröschel, R.2
  • 16
    • 0344515364 scopus 로고    scopus 로고
    • 8-glycosylated 8-aza-7-deazaguanine and self-assembly of 8-aza-7-deazapurines on the nucleoside and the oligomeric level
    • in press
    • 8-glycosylated 8-aza-7-deazaguanine and self-assembly of 8-aza-7-deazapurines on the nucleoside and the oligomeric level. Org. Biomol. Chem., in press.
    • (2003) Org. Biomol. Chem.
    • Seela, F.1    Kröschel, R.2
  • 17
    • 0022779159 scopus 로고
    • Can the double helix be parallel?
    • Pattabiraman,N. (1986) Can the double helix be parallel? Biopolymers, 25, 1603-1606.
    • (1986) Biopolymers , vol.25 , pp. 1603-1606
    • Pattabiraman, N.1
  • 19
    • 0027390393 scopus 로고
    • Solution structure of the parallel-stranded hairpin d(T8<>C4A8) as determined by two-dimensional NMR
    • Zhou,N., Germann,M.W., van de Sande,J.H., Pattabiraman,N. and Vogel,H.J. (1993) Solution structure of the parallel-stranded hairpin d(T8<>C4A8) as determined by two-dimensional NMR. Biochemistry, 32, 646-656.
    • (1993) Biochemistry , vol.32 , pp. 646-656
    • Zhou, N.1    Germann, M.W.2    van de Sande, J.H.3    Pattabiraman, N.4    Vogel, H.J.5
  • 20
    • 0031660471 scopus 로고    scopus 로고
    • Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine: Cytosine and isocytosine: Guanine basepairs by nuclear magnetic resonance spectroscopy
    • Yang,X.-L., Sugiyama,H., Ikeda,S., Saito,I. and Wang,A.H.-J. (1998) Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine: cytosine and isocytosine: guanine basepairs by nuclear magnetic resonance spectroscopy. Biophys. J., 75, 1163-1171.
    • (1998) Biophys. J. , vol.75 , pp. 1163-1171
    • Yang, X.-L.1    Sugiyama, H.2    Ikeda, S.3    Saito, I.4    Wang, A.H.-J.5
  • 21
    • 0035873531 scopus 로고    scopus 로고
    • Pyrazolo[3,4-d]pyrimidine nucleic acids: Adjustment of dA-dT to dG-dC base pair stability
    • Seela,F. and Becher,G. (2001) Pyrazolo[3,4-d]pyrimidine nucleic acids: adjustment of dA-dT to dG-dC base pair stability. Nucleic Acids Res., 29, 2069-2078.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 2069-2078
    • Seela, F.1    Becher, G.2
  • 22
    • 0032894327 scopus 로고    scopus 로고
    • The base-pairing properties of 7-deaza-2′-deoxyisoguanosine and 2′-deoxyisoguanosine in oligonucleotide duplexes with parallel and antiparallel chain orientation
    • Seela,F. and, Wei,C. (1999) The base-pairing properties of 7-deaza-2′-deoxyisoguanosine and 2′-deoxyisoguanosine in oligonucleotide duplexes with parallel and antiparallel chain orientation. Helv. Chim. Acta, 82, 726-745.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 726-745
    • Seela, F.1    Wei, C.2
  • 23
    • 0032808234 scopus 로고    scopus 로고
    • Parallel-stranded DNA formed by new base pairs related to the isoguanine-cytosine or isocytosine-guanine motifs
    • Seela,F., Wei,C., Melenewski,A., He,Y., Kröschel,R. and Feiling,E. (1999) Parallel-stranded DNA formed by new base pairs related to the isoguanine-cytosine or isocytosine-guanine motifs. Nucl. Nucl., 18, 1543-1548.
    • (1999) Nucl. Nucl. , vol.18 , pp. 1543-1548
    • Seela, F.1    Wei, C.2    Melenewski, A.3    He, Y.4    Kröschel, R.5    Feiling, E.6
  • 24
    • 0028310406 scopus 로고
    • Facile synthesis of 2′-deoxyisoguanosine and related 2′,3′-dideoxyribonucleosides
    • Seela,F. and Gabler,B. (1994) Facile synthesis of 2′-deoxyisoguanosine and related 2′,3′-dideoxyribonucleosides. Helv. Chim. Acta, 77, 622-630.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 622-630
    • Seela, F.1    Gabler, B.2
  • 25
    • 0034839809 scopus 로고    scopus 로고
    • Parallel DNA containing pyrazolo[3,4-d]pyrimidine analogues of isoguanine
    • Seela,F., Kröschel,R. and He,Y. (2001) Parallel DNA containing pyrazolo[3,4-d]pyrimidine analogues of isoguanine. Nucl. Nucl., 20, 1283-1286.
    • (2001) Nucl. Nucl. , vol.20 , pp. 1283-1286
    • Seela, F.1    Kröschel, R.2    He, Y.3
  • 26
    • 84987487263 scopus 로고
    • 2′-Deoxyisoguanosine and base-modified analogues: Chemical and photochemical synthesis
    • Kazimierczuk,Z., Mertens,R., Kawczynski,W. and Seela,F. (1991) 2′-Deoxyisoguanosine and base-modified analogues: chemical and photochemical synthesis. Helv. Chim. Acta, 74, 1742-1748.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 1742-1748
    • Kazimierczuk, Z.1    Mertens, R.2    Kawczynski, W.3    Seela, F.4
  • 28
    • 0004307689 scopus 로고    scopus 로고
    • Applied Biosystems, Weiterstadt, Germany
    • Users' Manual of the DNA Synthesizer. Applied Biosystems, Weiterstadt, Germany, p. 392.
    • Users' Manual of the DNA Synthesizer , pp. 392
  • 29
    • 0029805937 scopus 로고    scopus 로고
    • 2 by two-dimensional NMR and simulated annealing
    • 2 by two-dimensional NMR and simulated annealing. Biochemistry, 35, 14077-14089.
    • (1996) Biochemistry , vol.35 , pp. 14077-14089
    • McDowell, J.A.1    Turner, D.H.2
  • 30
    • 0036009267 scopus 로고    scopus 로고
    • Modified purine nucleosides as dangling ends of DNA duplexes: The effect of the nucleobase polarizability on stacking interactions
    • Rosemeyer,H. and Seela,F. (2002) Modified purine nucleosides as dangling ends of DNA duplexes: the effect of the nucleobase polarizability on stacking interactions. J. Chem. Soc., Perkin Trans., 2, 746-750.
    • (2002) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 746-750
    • Rosemeyer, H.1    Seela, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.