메뉴 건너뛰기




Volumn 33, Issue 8, 2005, Pages 2452-2463

Cyclohexenyl nucleic acids: Conformationally flexible oligonucleotides

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; CYTOSINE; DEOXYRIBOSE; DOUBLE STRANDED DNA; GUANINE; MONOMER; NUCLEIC ACID; NUCLEOSIDE DERIVATIVE; OLIGONUCLEOTIDE; THYMINE; TRITIUM; CYCLOHEXANE DERIVATIVE; NUCLEOSIDE; OLIGODEOXYRIBONUCLEOTIDE;

EID: 18244368996     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gki538     Document Type: Article
Times cited : (29)

References (55)
  • 1
    • 0037062978 scopus 로고    scopus 로고
    • The antiquity of RNA-based evolution
    • Joyce, G.F. (2002) The antiquity of RNA-based evolution. Nature, 418, 214-221.
    • (2002) Nature , vol.418 , pp. 214-221
    • Joyce, G.F.1
  • 3
    • 0000062563 scopus 로고
    • Far-infrared spectra, two-dimensional vibrational potential energy surface, and conformation of cyclohexene and its isotopomers
    • River-Gaines, V.E., Leibowitz, S.J. and Laane, J. (1991) Far-infrared spectra, two-dimensional vibrational potential energy surface, and conformation of cyclohexene and its isotopomers. J. Am. Chem. Soc., 113, 9735-9742.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9735-9742
    • River-Gaines, V.E.1    Leibowitz, S.J.2    Laane, J.3
  • 4
    • 84984929707 scopus 로고
    • On the potential energy surface for ring inversion in cyclohexene and related molecules
    • Anet, F.A.L., Freedberg, D.I., Storer, J.W. and Nouk, K.N. (1992) On the potential energy surface for ring inversion in cyclohexene and related molecules. J. Am. Chem. Soc., 114, 10969-10971.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10969-10971
    • Anet, F.A.L.1    Freedberg, D.I.2    Storer, J.W.3    Nouk, K.N.4
  • 5
    • 84950546370 scopus 로고
    • The barrier to interconversion of cyclohexene
    • Laane, J. and Choo, J. (1994) The barrier to interconversion of cyclohexene. J. Am. Chem. Soc., 116, 3889-3891.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3889-3891
    • Laane, J.1    Choo, J.2
  • 6
    • 85011942461 scopus 로고    scopus 로고
    • Cyclohexene nucleic acids: Serum stable oligonucleotides that activate RNase H and increase duplex stability with complementary RNA
    • Herdewijn, P. (2001) Cyclohexene nucleic acids: Serum stable oligonucleotides that activate RNase H and increase duplex stability with complementary RNA. Abstr. Pap. Am. Chem. Soc., 221, U155.
    • (2001) Abstr. Pap. Am. Chem. Soc. , vol.221
    • Herdewijn, P.1
  • 7
    • 0035907480 scopus 로고    scopus 로고
    • The cyclohexene ring as bioisostere of a furanose ring: Synthesis and antiviral activity of cyclohexenyl nucleosides
    • Herdewijn, P. and De Clercq, E. (2001) The cyclohexene ring as bioisostere of a furanose ring: Synthesis and antiviral activity of cyclohexenyl nucleosides. Bioorg. Med. Chem. Lett., 11, 1591-1597.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1591-1597
    • Herdewijn, P.1    De Clercq, E.2
  • 8
    • 0035945253 scopus 로고    scopus 로고
    • RNase H mediated cleavage of RNA by cyclohexene nucleic acid (CeNA)
    • Verbeure, B., Lescrinier, E., Wang, J. and Herdewijn, P. (2001) RNase H mediated cleavage of RNA by cyclohexene nucleic acid (CeNA). Nucleic Acids Res., 29, 4941-4947.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 4941-4947
    • Verbeure, B.1    Lescrinier, E.2    Wang, J.3    Herdewijn, P.4
  • 11
    • 0033999070 scopus 로고    scopus 로고
    • The cyclohexene ring system as a furanose mimic: Synthesis and antiviral activity of both enantiomers of cyclohexenylguanine
    • Wang, J., Froeyen, M., Hendrix, C., Andrei, G., Snoeck, R., De Clercq, E. and Herdewijn, P. (2000) The cyclohexene ring system as a furanose mimic: Synthesis and antiviral activity of both enantiomers of cyclohexenylguanine. J. Med. Chem., 43, 736-745.
    • (2000) J. Med. Chem. , vol.43 , pp. 736-745
    • Wang, J.1    Froeyen, M.2    Hendrix, C.3    Andrei, G.4    Snoeck, R.5    De Clercq, E.6    Herdewijn, P.7
  • 12
    • 0032695064 scopus 로고    scopus 로고
    • Enantioselective synthesis and conformational study of cyclohexene carbocyclic nucleosides
    • Wang, J. and Herdewijn, P. (1999) Enantioselective synthesis and conformational study of cyclohexene carbocyclic nucleosides. J. Org. Chem., 64, 7820-7827.
    • (1999) J. Org. Chem. , vol.64 , pp. 7820-7827
    • Wang, J.1    Herdewijn, P.2
  • 13
    • 0032991950 scopus 로고    scopus 로고
    • Enantioselective synthesis and conformational analysis of cyclohexene carbocyclic nucleosides
    • Wang, J. and Herdewijn, P. (1999) Enantioselective synthesis and conformational analysis of cyclohexene carbocyclic nucleosides. Nucleosides Nucleotides, 18, 593-594.
    • (1999) Nucleosides Nucleotides , vol.18 , pp. 593-594
    • Wang, J.1    Herdewijn, P.2
  • 14
    • 0015511563 scopus 로고
    • Conformational-analysis of sugar ring in nucleosides and nucleotides - New description using concept of pseudorotation
    • Altona, C. and Sundaralingam, M. (1972) Conformational-analysis of sugar ring in nucleosides and nucleotides - new description using concept of pseudorotation. J. Am. Chem. Soc., 94, 8205-8212.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 8205-8212
    • Altona, C.1    Sundaralingam, M.2
  • 15
    • 0000870931 scopus 로고
    • The conformation of 6-membered rings described by puckering coordinates derived from endocyclic torsion angles
    • Haasnoot, C.A.G. (1992) The conformation of 6-membered rings described by puckering coordinates derived from endocyclic torsion angles. J. Am. Chem. Soc., 114, 882-887.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 882-887
    • Haasnoot, C.A.G.1
  • 16
    • 84985069908 scopus 로고
    • Nucleic-acid constituents. 13. Empirical correlations between conformational parameters in beta-D-furanoside fragments derived from a statistical-survey of crystal-structures of nucleic-acid constituents - Full description of nucleoside molecular geometries in terms of 4 parameters
    • De leeuw, H.P.M., Haasnoot, C.A.G. and Altona, C. (1980) Nucleic-acid constituents. 13. Empirical correlations between conformational parameters in beta-D-furanoside fragments derived from a statistical-survey of crystal-structures of nucleic-acid constituents - full description of nucleoside molecular geometries in terms of 4 parameters. Isr. J. Chem., 20, 108-126.
    • (1980) Isr. J. Chem. , vol.20 , pp. 108-126
    • De leeuw, H.P.M.1    Haasnoot, C.A.G.2    Altona, C.3
  • 19
    • 0025390935 scopus 로고
    • Mopac - A semiempirical molecular-orbital program
    • Stewart, J.J.P. (1990) Mopac - a semiempirical molecular-orbital program. J. Comput. Aid. Mol. Des., 4, 1-45.
    • (1990) J. Comput. Aid. Mol. Des. , vol.4 , pp. 1-45
    • Stewart, J.J.P.1
  • 20
    • 84988129057 scopus 로고
    • Optimization of parameters for semiempirical methods. 1. method
    • Stewart, J.J.P. (1989) Optimization of parameters for semiempirical methods.1. method. J. Comput. Chem., 10, 209-220.
    • (1989) J. Comput. Chem. , vol.10 , pp. 209-220
    • Stewart, J.J.P.1
  • 21
    • 84988073214 scopus 로고
    • Optimization of parameters for semiempirical methods. 2. applications
    • Stewart, J.J.P. (1989) Optimization of parameters for semiempirical methods. 2. applications. J. Comput. Chem., 10, 221-264.
    • (1989) J. Comput. Chem. , vol.10 , pp. 221-264
    • Stewart, J.J.P.1
  • 23
    • 84988053694 scopus 로고
    • An all atom force-field for simulations of proteins and nucleic-acids
    • Weiner, S.J., Kollman, P.A., Nguyen, D.T. and Case, D.A. (1986) An all atom force-field for simulations of proteins and nucleic-acids. J. Comput. Chem., 7, 230-252.
    • (1986) J. Comput. Chem. , vol.7 , pp. 230-252
    • Weiner, S.J.1    Kollman, P.A.2    Nguyen, D.T.3    Case, D.A.4
  • 24
    • 0013575334 scopus 로고
    • Relationships between torsion angles and ring-puckering coordinates. 3. Application to heterocyclic puckered 5-membered rings
    • de Leeuw, F.A.A.M., Vankampen, P.N., Altona, C., Diez, E. and Esteban, A.L. (1984) Relationships between torsion angles and ring-puckering coordinates. 3. Application to heterocyclic puckered 5-membered rings. J. Mol. Struct., 125, 67-88.
    • (1984) J. Mol. Struct. , vol.125 , pp. 67-88
    • de Leeuw, F.A.A.M.1    Vankampen, P.N.2    Altona, C.3    Diez, E.4    Esteban, A.L.5
  • 25
    • 0015913888 scopus 로고
    • Conformational-analysis of sugar ring in nucleosides and nucleotides - Improved method for interpretation of proton magnetic-resonance coupling-constants
    • Altona, C. and Sundaralingam, M. (1973) Conformational-analysis of sugar ring in nucleosides and nucleotides - improved method for interpretation of proton magnetic-resonance coupling-constants. J. Am. Chem. Soc., 95, 2333-2344.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2333-2344
    • Altona, C.1    Sundaralingam, M.2
  • 26
    • 20444483055 scopus 로고
    • The relationship between proton-proton NMR coupling-constants and substituent electronegativities.1. An empirical generalization of the Karplus equation
    • Haasnoot, C.A.G., de Leeuw, F.A.A.M. and Altona, C. (1980) The relationship between proton-proton NMR coupling-constants and substituent electronegativities.1. An empirical generalization of the Karplus equation. Tetrahedron, 36, 2783-2792.
    • (1980) Tetrahedron , vol.36 , pp. 2783-2792
    • Haasnoot, C.A.G.1    de Leeuw, F.A.A.M.2    Altona, C.3
  • 28
    • 37049093263 scopus 로고
    • Conformational-analysis of beta-D-ribo-nucleosides, beta-D-deoxyribo-nucleosides, beta-D-arabino-nucleosides, beta-D-xylo-nucleosides, and beta-D-Lyxo-Nucleosides from proton-proton coupling-constants
    • de Leeuw, F.A.A.M. and Altona, C. (1982) Conformational-analysis of beta-D-ribo-nucleosides, beta-D-deoxyribo-nucleosides, beta-D-arabino-nucleosides, beta-D-xylo-nucleosides, and beta-D-Lyxo-Nucleosides from proton-proton coupling-constants. J. Chem. Soc. Perkin Trans., 2, 375-384.
    • (1982) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 375-384
    • de Leeuw, F.A.A.M.1    Altona, C.2
  • 29
    • 84956382691 scopus 로고
    • The relationship between proton-proton NMR coupling-constants and substituent electronegativities. 2. Conformational-analysis of the sugar ring in nucleosides and nucleotides in solution using a generalized Karplus equation
    • Haasnoot, C.A.G., de Leeuw, F.A.A.M., De leeuw, H.P.M. and Altona, C. (1981) The relationship between proton-proton NMR coupling-constants and substituent electronegativities. 2. Conformational-analysis of the sugar ring in nucleosides and nucleotides in solution using a generalized Karplus equation. Org. Magn. Reson., 15, 43-52.
    • (1981) Org. Magn. Reson. , vol.15 , pp. 43-52
    • Haasnoot, C.A.G.1    de Leeuw, F.A.A.M.2    De leeuw, H.P.M.3    Altona, C.4
  • 30
    • 2642628181 scopus 로고
    • A two-dimensional nuclear overhauser experiment with pure absorption phase in 4 quadrants
    • States, D.J., Haberkorn, R.A. and Ruben, D.J. (1982) A two-dimensional nuclear overhauser experiment with pure absorption phase in 4 quadrants. J. Magn. Reson., 48, 286-292.
    • (1982) J. Magn. Reson. , vol.48 , pp. 286-292
    • States, D.J.1    Haberkorn, R.A.2    Ruben, D.J.3
  • 31
    • 33845555707 scopus 로고
    • Exchangeable proton NMR without base-line distortion, using new strong-pulse sequences
    • Plateau, P. and Gueron, M. (1982) Exchangeable proton NMR without base-line distortion, using new strong-pulse sequences. J. Am. Chem. Soc., 104, 7310-7311.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7310-7311
    • Plateau, P.1    Gueron, M.2
  • 32
    • 0026951903 scopus 로고
    • Gradient-tailored excitation for single-quantum NMR-spectroscopy of aqueous-solutions
    • Piotto, M., Saudek, V. and Sklenar, V. (1992) Gradient-tailored excitation for single-quantum NMR-spectroscopy of aqueous-solutions. J. Biomol. NMR, 2, 661-665.
    • (1992) J. Biomol. NMR , vol.2 , pp. 661-665
    • Piotto, M.1    Saudek, V.2    Sklenar, V.3
  • 34
    • 5144233105 scopus 로고
    • Mlev-17-based two-dimensional homonuclear magnetization transfer spectroscopy
    • Bax, A. and Davis, D.G. (1985) Mlev-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson., 65, 355-360.
    • (1985) J. Magn. Reson. , vol.65 , pp. 355-360
    • Bax, A.1    Davis, D.G.2
  • 35
    • 0343359244 scopus 로고
    • Investigation of exchange processes by 2-dimensional NMR-spectroscopy
    • Jeener, J., Meier, B.H., Bachmann, P. and Ernst, R.R. (1979) Investigation of exchange processes by 2-dimensional NMR-spectroscopy. J. Chem. Phys., 71, 4546-4553.
    • (1979) J. Chem. Phys. , vol.71 , pp. 4546-4553
    • Jeener, J.1    Meier, B.H.2    Bachmann, P.3    Ernst, R.R.4
  • 36
    • 0024282849 scopus 로고
    • Clean tocsy for H-1 spin system-identification in macromolecules
    • Griesinger, C., Otting, G., Wuthrich, K. and Ernst, R.R. (1988) Clean tocsy for H-1 spin system-identification in macromolecules. J. Am. Chem. Soc., 110, 7870-7872.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7870-7872
    • Griesinger, C.1    Otting, G.2    Wuthrich, K.3    Ernst, R.R.4
  • 37
    • 0023046345 scopus 로고
    • Assignment of the P-31 and H-1 resonances in oligonucleotides by two-dimensional NMR-spectroscopy
    • Sklenar, V., Miyashiro, H., Zon, G., Miles, H.T. and Bax, A. (1986) Assignment of the P-31 and H-1 resonances in oligonucleotides by two-dimensional NMR-spectroscopy. FEBS Lett., 208, 94-98.
    • (1986) FEBS Lett. , vol.208 , pp. 94-98
    • Sklenar, V.1    Miyashiro, H.2    Zon, G.3    Miles, H.T.4    Bax, A.5
  • 40
    • 0000353016 scopus 로고    scopus 로고
    • The use of NMR methods for conformational studies of nucleic acids
    • Wijmenga, S.S. and van Buuren, B.N.M. (1998) The use of NMR methods for conformational studies of nucleic acids. Prog. Nucl. Magn. Reson. Spectrosc., 32, 287-387.
    • (1998) Prog. Nucl. Magn. Reson. Spectrosc. , vol.32 , pp. 287-387
    • Wijmenga, S.S.1    van Buuren, B.N.M.2
  • 41
    • 0030621858 scopus 로고    scopus 로고
    • Torsion-angle molecular dynamics as a new efficient tool for NMR structure calculation
    • Stein, E.G., Rice, L.M. and Brunger, A.T. (1997) Torsion-angle molecular dynamics as a new efficient tool for NMR structure calculation. J. Magn. Reson., 124, 154-164.
    • (1997) J. Magn. Reson. , vol.124 , pp. 154-164
    • Stein, E.G.1    Rice, L.M.2    Brunger, A.T.3
  • 42
    • 0034698001 scopus 로고    scopus 로고
    • A-form conformational motifs in ligand-bound DNA structures
    • Lu, X.J., Shakked, Z. and Olson, W.K. (2000) A-form conformational motifs in ligand-bound DNA structures. J. Mol. Biol., 300, 819-840.
    • (2000) J. Mol. Biol. , vol.300 , pp. 819-840
    • Lu, X.J.1    Shakked, Z.2    Olson, W.K.3
  • 43
    • 0026244229 scopus 로고
    • MOLSCRIPT: A program to produce both detailed and schematic plots of protein structures
    • Kraulis, P.J. (1991) MOLSCRIPT: A program to produce both detailed and schematic plots of protein structures. J. Appl. Crystallogr., 24, 946-950.
    • (1991) J. Appl. Crystallogr. , vol.24 , pp. 946-950
    • Kraulis, P.J.1
  • 44
    • 0030729838 scopus 로고    scopus 로고
    • An extensively modified version of molscript that includes generally enhanced colouring capabilities
    • Esnouf, R.M. (1997) An extensively modified version of molscript that includes generally enhanced colouring capabilities. J. Mol. Graph. Model., 15, 132-134.
    • (1997) J. Mol. Graph. Model. , vol.15 , pp. 132-134
    • Esnouf, R.M.1
  • 45
    • 33947092205 scopus 로고
    • Extreme conformational flexibility of furanose ring in DNA and RNA
    • Levitt, M. and Warshel, A. (1978) Extreme conformational flexibility of furanose ring in DNA and RNA. J. Am. Chem. Soc., 100, 2607-2613.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 2607-2613
    • Levitt, M.1    Warshel, A.2
  • 46
    • 0019923858 scopus 로고
    • How flexible is the furanose ring. 2. An updated potential-energy estimate
    • Olson, W.K. (1982) How flexible is the furanose ring. 2. An updated potential-energy estimate. J. Am. Chem. Soc., 104, 278-286.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 278-286
    • Olson, W.K.1
  • 47
    • 0019912345 scopus 로고
    • How flexible is the furanose ring. 1. A comparison of experimental and theoretical-studies
    • Olson, W.K. and Sussman, J.L. (1982) How flexible is the furanose ring. 1. A comparison of experimental and theoretical-studies. J. Am. Chem. Soc., 104, 270-278.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 270-278
    • Olson, W.K.1    Sussman, J.L.2
  • 50
    • 0035742338 scopus 로고    scopus 로고
    • Measurement of homonuclear proton couplings from regular 2D COSY spectra
    • Delaglio, F., Wu, Z.R. and Bax, A. (2001) Measurement of homonuclear proton couplings from regular 2D COSY spectra. J. Magn. Reson., 149, 276-281.
    • (2001) J. Magn. Reson. , vol.149 , pp. 276-281
    • Delaglio, F.1    Wu, Z.R.2    Bax, A.3
  • 51
    • 0038239273 scopus 로고    scopus 로고
    • Difference in conformational diversity between nucleic acids with a six-membered 'sugar' unit and natural 'furanose' nucleic acids
    • Lescrinier, E., Froeyen, M. and Herdewijn, P. (2003) Difference in conformational diversity between nucleic acids with a six-membered 'sugar' unit and natural 'furanose' nucleic acids. Nucleic Acids Res., 31, 2975-2989.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 2975-2989
    • Lescrinier, E.1    Froeyen, M.2    Herdewijn, P.3
  • 52
    • 0002183131 scopus 로고    scopus 로고
    • Polynucleotide secondary structures: An historical perspective
    • Neidle, S. (ed.), Oxford Press, Oxford
    • Arnott, S. (1999) Polynucleotide secondary structures: An historical perspective. In Neidle, S. (ed.), Oxford Handbook of Nucleic Acid Structure. Oxford Press, Oxford, pp. 1-38.
    • (1999) Oxford Handbook of Nucleic Acid Structure , pp. 1-38
    • Arnott, S.1
  • 53
    • 0344438824 scopus 로고    scopus 로고
    • DNA and RNA structure
    • Blackburn, G.M. and Gait, M.J. (eds), Oxford University Press, Oxford
    • Blackburn, G.M. and Gait, M.J. (1996) DNA and RNA structure. In Blackburn, G.M. and Gait, M.J. (eds), Nucleic Acids in Chemistry and Biology. Oxford University Press, Oxford, pp. 28-39.
    • (1996) Nucleic Acids in Chemistry and Biology , pp. 28-39
    • Blackburn, G.M.1    Gait, M.J.2
  • 54
    • 3342893036 scopus 로고    scopus 로고
    • Partial B-to-A DNA transition upon minor groove binding of protein Sac7d monitored by Raman spectroscopy
    • Dostal, L., Chen, C.Y., Wang, A.H. and Welfle, H. (2004) Partial B-to-A DNA transition upon minor groove binding of protein Sac7d monitored by Raman spectroscopy. Biochemistry, 43, 9600-9609.
    • (2004) Biochemistry , vol.43 , pp. 9600-9609
    • Dostal, L.1    Chen, C.Y.2    Wang, A.H.3    Welfle, H.4
  • 55
    • 0032743844 scopus 로고    scopus 로고
    • Conformationally restricted carbohydrate-modified nucleic acids and antisense technology
    • Herdewijn, P. (1999) Conformationally restricted carbohydrate-modified nucleic acids and antisense technology. Biochim. Biophys. Acta, 1489, 167-179.
    • (1999) Biochim. Biophys. Acta , vol.1489 , pp. 167-179
    • Herdewijn, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.