메뉴 건너뛰기




Volumn 30, Issue 24, 2002, Pages 5485-5496

Propypnyl groups in duplex DNA: Stability of base pairs incorporating 7-substituted 8-aza-7-deazapurines or 5-substituted pyrimidines

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DERIVATIVE; DEOXYCYTIDINE; DEOXYURIDINE; DIAMINE DERIVATIVE; DOUBLE STRANDED DNA; GUANOSINE DERIVATIVE; NUCLEIC ACID BASE; NUCLEOSIDE; OLIGONUCLEOTIDE; PROPYNYL DERIVATIVE; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; HETERODUPLEX;

EID: 0037114031     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/gkf689     Document Type: Review
Times cited : (63)

References (37)
  • 1
    • 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
  • 3
    • 0031911386 scopus 로고    scopus 로고
    • Synthesis of 7-halogenated 8-aza-7-deaza-2′-deoxy-guanosines and related pyrazolo[3,4-d]pyrimidine 2′-deoxyribonucleosides
    • Seela,F. and Becher,G. (1998) Synthesis of 7-halogenated 8-aza-7-deaza-2′-deoxy-guanosines and related pyrazolo[3,4-d]pyrimidine 2′-deoxyribonucleosides. Synthesis, 207-214.
    • (1998) Synthesis , pp. 207-214
    • Seela, F.1    Becher, G.2
  • 4
    • 0022971726 scopus 로고
    • Synthesis of 2′-deoxyribofuranosides of 8-aza-7-deazaguanine and related pyrazolo[3,4-d]pyrimidines
    • Seela,F. and Steker,H. (1986) Synthesis of 2′-deoxyribofuranosides of 8-aza-7-deazaguanine and related pyrazolo[3,4-d]pyrimidines. Helv. Chim. Acta, 69, 1602-1613.
    • (1986) Helv. Chim. Acta , vol.69 , pp. 1602-1613
    • Seela, F.1    Steker, H.2
  • 5
    • 0012613164 scopus 로고
    • Synthesis of 7-deaza-2′-deoxyguanosine by phase-transfer glycosylation and preparation of suitable derivatives for oligonucleotide synthesis
    • Seela,F., Winkeler,H.-D., Driller,H. and Menkhoff,S. (1984) Synthesis of 7-deaza-2′-deoxyguanosine by phase-transfer glycosylation and preparation of suitable derivatives for oligonucleotide synthesis. Nucleic Acids Res., 14, 245-246.
    • (1984) Nucleic Acids Res. , vol.14 , pp. 245-246
    • Seela, F.1    Winkeler, H.-D.2    Driller, H.3    Menkhoff, S.4
  • 6
    • 0021984195 scopus 로고
    • Facile synthesis of 2′-deoxyribofuranosides of allopurinol and 4-amino-1H-pyrazolo-[3,4-d]pyrimidine via phase-transfer glycosylation
    • Seela,F. and Steker,H. (1985) Facile synthesis of 2′-deoxyribofuranosides of allopurinol and 4-amino-1H-pyrazolo-[3,4-d]pyrimidine via phase-transfer glycosylation. Helv. Chim. Acta, 68, 563-570.
    • (1985) Helv. Chim. Acta , vol.68 , pp. 563-570
    • Seela, F.1    Steker, H.2
  • 7
    • 0012612171 scopus 로고    scopus 로고
    • Synthesis of 7-alkynylated 8-aza-7-deaza-2′-deoxy-adenosines via the Pd-catalysed cross-coupling reaction
    • Seela,F. and Zulauf,M. (1998) Synthesis of 7-alkynylated 8-aza-7-deaza-2′-deoxy-adenosines via the Pd-catalysed cross-coupling reaction. J. Chem. Soc. [Perkin 1], 3233-3239.
    • (1998) J. Chem. Soc. [Perkin 1] , pp. 3233-3239
    • Seela, F.1    Zulauf, M.2
  • 8
    • 0030780913 scopus 로고    scopus 로고
    • Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine
    • Haaima,G., Hansen,H.F., Christensen,L., Dahl,O. and Nielsen,P.E. (1997) Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine. Nucleic Acids Res., 25, 4639-4643.
    • (1997) Nucleic Acids Res. , vol.25 , pp. 4639-4643
    • Haaima, G.1    Hansen, H.F.2    Christensen, L.3    Dahl, O.4    Nielsen, P.E.5
  • 9
    • 0027240213 scopus 로고
    • Antisense oligodeoxynucleotides: Synthesis, biophysical and biological evaluation of oligodeoxynucleotides containing modified pyrimidines
    • Sanghvi,Y.S., Hoke,G.D., Freier,S.M., Zounes,M.C., Gonzalez,C., Cummins,L., Sasmor,H. and Cook,P.D. (1993) Antisense oligodeoxynucleotides: synthesis, biophysical and biological evaluation of oligodeoxynucleotides containing modified pyrimidines. Nucleic Acids Res., 21, 3197-3203.
    • (1993) Nucleic Acids Res. , vol.21 , pp. 3197-3203
    • Sanghvi, Y.S.1    Hoke, G.D.2    Freier, S.M.3    Zounes, M.C.4    Gonzalez, C.5    Cummins, L.6    Sasmor, H.7    Cook, P.D.8
  • 10
    • 0033990407 scopus 로고    scopus 로고
    • Use of minimally modified antisense oligonucleotides for specific inhibition of gene expression
    • Uhlmann,E., Peyman,A., Ryte,A., Schmidt,A. and Buddecke,E. (2000) Use of minimally modified antisense oligonucleotides for specific inhibition of gene expression. Methods Enzymol., 313, 268-284.
    • (2000) Methods Enzymol. , vol.313 , pp. 268-284
    • Uhlmann, E.1    Peyman, A.2    Ryte, A.3    Schmidt, A.4    Buddecke, E.5
  • 11
    • 0025815089 scopus 로고
    • Antisense probes containing 2-aminoadenosine allow efficient depletion of U5 snRNP from HeLa splicing extracts
    • Lamm,G.M., Blencowe,B.J., Sproat,B.S., Iribarren,A.M., Ryder,U. and Lamond,A.I. (1991) Antisense probes containing 2-aminoadenosine allow efficient depletion of U5 snRNP from HeLa splicing extracts. Nucleic Acids Res., 19, 3193-3197.
    • (1991) Nucleic Acids Res. , vol.19 , pp. 3193-3197
    • Lamm, G.M.1    Blencowe, B.J.2    Sproat, B.S.3    Iribarren, A.M.4    Ryder, U.5    Lamond, A.I.6
  • 12
    • 0032189085 scopus 로고    scopus 로고
    • The use of diaminopurine to investigate structural properties of nucleic acids and molecular recognition between ligands and DNA
    • Bailly,C. and Waring,M.J. (1998) The use of diaminopurine to investigate structural properties of nucleic acids and molecular recognition between ligands and DNA. Nucleic Acids Res., 26, 4309-4314.
    • (1998) Nucleic Acids Res. , vol.26 , pp. 4309-4314
    • Bailly, C.1    Waring, M.J.2
  • 13
    • 0031681373 scopus 로고    scopus 로고
    • 7-Deazaadenine-DNA: Bulky 7-iodo substituents or hydrophobic 7-hexynyl chains are well accommodated in the major groove of oligonucleotide duplexes
    • Seela,F. and Zulauf,M. (1998) 7-Deazaadenine-DNA: bulky 7-iodo substituents or hydrophobic 7-hexynyl chains are well accommodated in the major groove of oligonucleotide duplexes. Chem. Eur. J., 4, 1781-1790.
    • (1998) Chem. Eur. J. , vol.4 , pp. 1781-1790
    • Seela, F.1    Zulauf, M.2
  • 14
    • 0001976141 scopus 로고    scopus 로고
    • Synthesis of oligonucleotides containing pyrazolo[3,4-d]pyrimidines: The influence of 7-substituted 8-aza-7-deazaadenines on the duplex structure and stability
    • Seela,F. and Zulauf,M. (1999) Synthesis of oligonucleotides containing pyrazolo[3,4-d]pyrimidines: the influence of 7-substituted 8-aza-7-deazaadenines on the duplex structure and stability. J. Chem. Soc. [Perkin 1], 479-488.
    • (1999) J. Chem. Soc. [Perkin 1] , pp. 479-488
    • Seela, F.1    Zulauf, M.2
  • 15
    • 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
  • 16
    • 0032780506 scopus 로고    scopus 로고
    • 8-Aza-7-deazapurine DNA: Synthesis and duplex stability of oligonucleotides containing 7-substituted bases
    • Seela,F., Becher,G. and Zulauf,M. (1999) 8-Aza-7-deazapurine DNA: synthesis and duplex stability of oligonucleotides containing 7-substituted bases. Nucl. Nucl., 18, 1399-1400.
    • (1999) Nucl. Nucl. , vol.18 , pp. 1399-1400
    • Seela, F.1    Becher, G.2    Zulauf, M.3
  • 17
    • 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
  • 18
    • 0037182016 scopus 로고    scopus 로고
    • 8-Aza-7-deazapurine-pyrimidine base pairs: The contribution of 2- and 7-substituents to the stability of duplex DNA
    • He,J. and Seela,F. (2002) 8-Aza-7-deazapurine-pyrimidine base pairs: the contribution of 2- and 7-substituents to the stability of duplex DNA. Tetrahedron, 58, 4535-4542.
    • (2002) Tetrahedron , vol.58 , pp. 4535-4542
    • He, J.1    Seela, F.2
  • 19
    • 0027462696 scopus 로고
    • Base-modified oligodeoxynucleotides. I. Effect of 5-alkyl, 5-(1-alkenyl) and 5-(1-alkynyl) substitution of the pyrimidines on duplex stability and hydrophobicity
    • Sági,J., Szemzö,A., Ébinger,K., Szabolcs,A., Sági,G., Ruff,É. and Ötvös,L. (1993) Base-modified oligodeoxynucleotides. I. Effect of 5-alkyl, 5-(1-alkenyl) and 5-(1-alkynyl) substitution of the pyrimidines on duplex stability and hydrophobicity. Tetrahedron Lett., 34, 2191-2194.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2191-2194
    • Sági, J.1    Szemzö, A.2    Ébinger, K.3    Szabolcs, A.4    Sági, G.5    Ruff, É.6    Ötvös, L.7
  • 20
    • 0034794425 scopus 로고    scopus 로고
    • Long-range cooperativity in molecular recognition of RNA by oligodeoxynucleotides with multiple C5-(1-propynyl) pyrimidines
    • Barnes,T.W.,III and Turner,D.H. (2001) Long-range cooperativity in molecular recognition of RNA by oligodeoxynucleotides with multiple C5-(1-propynyl) pyrimidines. J. Am. Chem. Soc., 123, 4107-4118.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4107-4118
    • Barnes T.W. III1    Turner, D.H.2
  • 21
    • 0035940485 scopus 로고    scopus 로고
    • C5-(1-propynyl)-2′-deoxy-pyrimidines enhance mismatch penalties of DNA:RNA duplex formation
    • Barnes,T.W.,III and Turner,D.H. (2001) C5-(1-propynyl)-2′-deoxy-pyrimidines enhance mismatch penalties of DNA:RNA duplex formation. Biochemistry, 40, 12738-12745.
    • (2001) Biochemistry , vol.40 , pp. 12738-12745
    • Barnes T.W. III1    Turner, D.H.2
  • 23
    • 0026783155 scopus 로고
    • Oligodeoxynucleotides containing C-5 propyne analogs of 2′-deoxyuridine and 2′-deoxycytidine
    • Froehler,B.C., Wadwani,S., Terhorst,T.J. and Gerrard,S.R. (1992) Oligodeoxynucleotides containing C-5 propyne analogs of 2′-deoxyuridine and 2′-deoxycytidine. Tetrahedron Lett., 33, 5307-5310.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5307-5310
    • Froehler, B.C.1    Wadwani, S.2    Terhorst, T.J.3    Gerrard, S.R.4
  • 25
    • 0032125593 scopus 로고    scopus 로고
    • A comparative study of the thermal stability of oligodeoxyribonucleotides containing 5-substituted 2′-deoxyuridines
    • Ahmadian,M., Zhang,P. and Bergstrom,D.E. (1998) A comparative study of the thermal stability of oligodeoxyribonucleotides containing 5-substituted 2′-deoxyuridines. Nucleic Acids Res., 26, 3127-3135.
    • (1998) Nucleic Acids Res. , vol.26 , pp. 3127-3135
    • Ahmadian, M.1    Zhang, P.2    Bergstrom, D.E.3
  • 26
    • 33748590278 scopus 로고    scopus 로고
    • DNA duplexes stabilized by modified monomer residues: Synthesis and stability
    • Graham,D., Parkinson,J.A. and Brown,T. (1998) DNA duplexes stabilized by modified monomer residues: synthesis and stability. J. Chem. Soc. [Perkin 1], 1131-1138.
    • (1998) J. Chem. Soc. [Perkin 1] , pp. 1131-1138
    • Graham, D.1    Parkinson, J.A.2    Brown, T.3
  • 27
    • 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
  • 28
    • 0034605215 scopus 로고    scopus 로고
    • 2′-deoxy-8-(propyn-1-yl)adenosine-containing oligonucleotides: Effects on stability of duplex and quadruplex structures
    • Catalanotti,B., Galeone,A., Gomez-Paloma,L., Mayol,L. and Pepe,A. (2000) 2′-deoxy-8-(propyn-1-yl)adenosine-containing oligonucleotides: effects on stability of duplex and quadruplex structures. Bioorg. Med. Chem. Lett., 10, 2005-2009.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 2005-2009
    • Catalanotti, B.1    Galeone, A.2    Gomez-Paloma, L.3    Mayol, L.4    Pepe, A.5
  • 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
  • 31
    • 33845185176 scopus 로고
    • Palladium-catalyzed synthesis of alkynylamino nucleosides. A universal linker for nucleic acids
    • Hobbs,F.W. (1989) Palladium-catalyzed synthesis of alkynylamino nucleosides. A universal linker for nucleic acids. J. Org. Chem., 54, 3420-3422.
    • (1989) J. Org. Chem. , vol.54 , pp. 3420-3422
    • Hobbs, F.W.1
  • 32
    • 0025283720 scopus 로고
    • Solvent, not palladium oxidation state, is the primary determinant for successful coupling of terminal alkynes with iodo-nucleosides
    • Robins,M.J., Vinayak,R.S. and Wood,S.G. (1990) Solvent, not palladium oxidation state, is the primary determinant for successful coupling of terminal alkynes with iodo-nucleosides. Tetrahedron Lett., 31, 3731-3734.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3731-3734
    • Robins, M.J.1    Vinayak, R.S.2    Wood, S.G.3
  • 33
    • 21744445820 scopus 로고    scopus 로고
    • Alkynylated nucleosides and their analogues. I. Methods of synthesis
    • Korshun,V.A., Manasova,E.V. and Berlin,Yu.A. (1997) Alkynylated nucleosides and their analogues. I. Methods of synthesis. Russian J. Bioorg. Chem., 23, 300-362.
    • (1997) Russian J. Bioorg. Chem. , vol.23 , pp. 300-362
    • Korshun, V.A.1    Manasova, E.V.2    Berlin, Yu.A.3
  • 34
    • 0001518039 scopus 로고
    • Transient protection: Efficient one-flask syntheses of protected deoxynucleosides
    • Ti,G.S., Gaffney,B.L. and Jones,R.A. (1982) Transient protection: efficient one-flask syntheses of protected deoxynucleosides. J. Am. Chem. Soc., 104, 1316-1319.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 1316-1319
    • Ti, G.S.1    Gaffney, B.L.2    Jones, R.A.3
  • 36
    • 0032720771 scopus 로고    scopus 로고
    • Oligonucleotides containing 7-deazaadenines: The influence of the 7-substituent chain length and charge on the duplex stability
    • Seela,F. and Zulauf,M. (1999) Oligonucleotides containing 7-deazaadenines: the influence of the 7-substituent chain length and charge on the duplex stability. Helv. Chim. Acta, 82, 1878-1898.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 1878-1898
    • Seela, F.1    Zulauf, M.2
  • 37
    • 0030768415 scopus 로고    scopus 로고
    • 7-Deazaguanine DNA: Oligonucleotides with hydrophobic or cationic side chains
    • Ramzaeva,N., Mittelbach,C. and Seela,F. (1997) 7-Deazaguanine DNA: oligonucleotides with hydrophobic or cationic side chains. Helv. Chim. Acta, 80, 1809-1822.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 1809-1822
    • Ramzaeva, N.1    Mittelbach, C.2    Seela, F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.