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Volumn 36, Issue 6, 2008, Pages 1805-1812

Unexpected A-form formation of 4′-thioDNA in solution, revealed by NMR, and the implications as to the mechanism of nuclease resistance

Author keywords

[No Author keywords available]

Indexed keywords

4' THIODNA; ADENINE; CYTOSINE; GUANINE; NUCLEASE; OLIGONUCLEOTIDE; RNA; THYMINE; UNCLASSIFIED DRUG;

EID: 41849084875     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkn011     Document Type: Article
Times cited : (18)

References (42)
  • 1
    • 0027179417 scopus 로고    scopus 로고
    • (A93) Synthesis and properties of oligodeoxynuleotides containing the analogue 2′-deoxy-4′-thiothymidine
    • Hancox, E.L., Connolly,B.A. and Walker,R.T. (A93) Synthesis and properties of oligodeoxynuleotides containing the analogue 2′-deoxy-4′-thiothymidine. Nucleic Acids Res., 21, 3485-3491.
    • Nucleic Acids Res , vol.21 , pp. 3485-3491
    • Hancox, E.L.1    Connolly, B.A.2    Walker, R.T.3
  • 2
    • 0030789978 scopus 로고    scopus 로고
    • DNA containing 4′-thio-2′-deoxycytidine inhibits methylation by Hhal methyltransferase
    • Kumar,S., Horton,J.R., Jones,G.D., Walker,R.T., Roberts,R.J. and Cheng,X. (1997) DNA containing 4′-thio-2′-deoxycytidine inhibits methylation by Hhal methyltransferase. Nucleic Acids Res., 25 2773-2783.
    • (1997) Nucleic Acids Res , vol.25 , pp. 2773-2783
    • Kumar, S.1    Horton, J.R.2    Jones, G.D.3    Walker, R.T.4    Roberts, R.J.5    Cheng, X.6
  • 3
    • 0029963653 scopus 로고    scopus 로고
    • Investigation of some properties of oligodeoxynucleotides containing 4′-thio-2′-deoxynucleotides: Duplex hybridization and nuclease sensitivity
    • Jones,G.D., Lesnik,E.A., Owens,S.R., Risen,L.M. and Walker,R.T. (1996) Investigation of some properties of oligodeoxynucleotides containing 4′-thio-2′-deoxynucleotides: Duplex hybridization and nuclease sensitivity. Nucleic Acids Res., 24, 4117 -4122.
    • (1996) Nucleic Acids Res , vol.24 , pp. 4117-4122
    • Jones, G.D.1    Lesnik, E.A.2    Owens, S.R.3    Risen, L.M.4    Walker, R.T.5
  • 4
    • 0031579954 scopus 로고    scopus 로고
    • Duplax, and triplex-forming properties of 4′-thio-modified oligodeoxynucleotides
    • Jones,G.D., Altmann,K.-H., Huskeri,D. and Walker, R.T. (1997) Duplax, and triplex-forming properties of 4′-thio-modified oligodeoxynucleotides. Bioorg, Med. Chem. Lett., 7, 1275-1278.
    • (1997) Bioorg, Med. Chem. Lett , vol.7 , pp. 1275-1278
    • Jones, G.D.1    Altmann, K.-H.2    Huskeri, D.3    Walker, R.T.4
  • 5
    • 0028820184 scopus 로고
    • 4′-Thio-RNA synthesis of mixed base 4′-thio-oligoribonucleotides nuclease resistance, and base pairing properties with complementary single and double strand
    • Leydier,C., Bellon,L., Barascut,J.L., Morvan,F., Rayner,B. and, Imbach,J.L. (1995) 4′-Thio-RNA synthesis of mixed base 4′-thio-oligoribonucleotides nuclease resistance, and base pairing properties with complementary single and double strand. Antisense Res. Dev., 5, 167-174.
    • (1995) Antisense Res. Dev , vol.5 , pp. 167-174
    • Leydier, C.1    Bellon, L.2    Barascut, J.L.3    Morvan, F.4    Rayner, B.5    Imbach, J.L.6
  • 6
    • 26844449313 scopus 로고    scopus 로고
    • Practical synthesis of 2′-Deoxy-4′-thioribonucleosides: Substrates for the synthesis of 4′-ThioDNA
    • Inoue,N., Kaga,D., Minakawa,N. and Matsuda,A. (2005) Practical synthesis of 2′-Deoxy-4′-thioribonucleosides: Substrates for the synthesis of 4′-ThioDNA. J. Org. Chem., 70, 8597-8600.
    • (2005) J. Org. Chem , vol.70 , pp. 8597-8600
    • Inoue, N.1    Kaga, D.2    Minakawa, N.3    Matsuda, A.4
  • 7
    • 33746857804 scopus 로고    scopus 로고
    • Synthesis and properties of 4′-ThioDNA: Unexpected RNA-like behavior of 4′-ThioDNA
    • Inoue,N., Minakawa,N. and Matsuda,A. (2006) Synthesis and properties of 4′-ThioDNA: Unexpected RNA-like behavior of 4′-ThioDNA. Nucleic Acids Res., 34, 3476-3483.
    • (2006) Nucleic Acids Res , vol.34 , pp. 3476-3483
    • Inoue, N.1    Minakawa, N.2    Matsuda, A.3
  • 8
    • 0029963064 scopus 로고    scopus 로고
    • 2, a synthetic DNA dodecamer duplex containing four 4′-thio-2′-deoxythymidine nucleotides. Nucleic Acids Res., 24, 951-961.
    • 2, a synthetic DNA dodecamer duplex containing four 4′-thio-2′-deoxythymidine nucleotides. Nucleic Acids Res., 24, 951-961.
  • 9
    • 22844448221 scopus 로고    scopus 로고
    • Haeberli,P., Berger,I., Pallan,P.S. and Egli,M. Q005 Syntheses of 4′-thioribonucleosides and thermodynamic stability and Crystal structure of RNA oligomers with incorporated 4′-thiocytosine. Nucleic Acids Res., 33, 3965-3975.
    • Haeberli,P., Berger,I., Pallan,P.S. and Egli,M. Q005) Syntheses of 4′-thioribonucleosides and thermodynamic stability and Crystal structure of RNA oligomers with incorporated 4′-thiocytosine. Nucleic Acids Res., 33, 3965-3975.
  • 12
    • 0004040543 scopus 로고    scopus 로고
    • University of California, San Francisco
    • Goddard,T.D. and Kneller,D.G. (2006) SPARKY 3, University of California, San Francisco.
    • (2006) SPARKY 3
    • Goddard, T.D.1    Kneller, D.G.2
  • 13
    • 0037904751 scopus 로고    scopus 로고
    • Matsugami,A., Kobayashi,S., Ouhashi,K., Uesugi.S., Yamamoto,R., Taira,K., Nishikawa,S., Kumar,P.K.R. and Katahira,M. (2003) Structural basis of the highly efficient trapping of the HIV Tat protein by an RNA aptamer. Structure, 11, 533-545.
    • Matsugami,A., Kobayashi,S., Ouhashi,K., Uesugi.S., Yamamoto,R., Taira,K., Nishikawa,S., Kumar,P.K.R. and Katahira,M. (2003) Structural basis of the highly efficient trapping of the HIV Tat protein by an RNA aptamer. Structure, 11, 533-545.
  • 14
    • 0035914469 scopus 로고    scopus 로고
    • An intramolecular quadruplex or (GGA)(4) triplet repeat. DNA with a G:G:G:G retrad and a G(:A):G(:A):G(:A):G heptad, and its dimeric interaction
    • Matsugami,A., Ouhashi,K., Kanagawa,M., Liu,H., Kanagawa, S., Uesugi,S. and Katahira,M. (2001) An intramolecular quadruplex or (GGA)(4) triplet repeat. DNA with a G:G:G:G retrad and a G(:A):G(:A):G(:A):G heptad, and its dimeric interaction. J. Mol. Biol., 313, 255-269.
    • (2001) J. Mol. Biol , vol.313 , pp. 255-269
    • Matsugami, A.1    Ouhashi, K.2    Kanagawa, M.3    Liu, H.4    Kanagawa, S.5    Uesugi, S.6    Katahira, M.7
  • 15
    • 0042847316 scopus 로고    scopus 로고
    • Intramolecular higher oder packing of parallel quadruplexes comprismig a. G:G:G:G tetrad and a G(:A):G(:A):G(:A):G heptad of GGA triplet repeat DNA
    • Matsugami, A, Okuizumi, T., Uesugi,S. and Katahira,M. (2003) Intramolecular higher oder packing of parallel quadruplexes comprismig a. G:G:G:G tetrad and a G(:A):G(:A):G(:A):G heptad of GGA triplet repeat DNA. J. Biol. Chem., 278, 28147-28153.
    • (2003) J. Biol. Chem , vol.278 , pp. 28147-28153
    • Matsugami, A.1    Okuizumi, T.2    Uesugi, S.3    Katahira, M.4
  • 17
    • 0034674037 scopus 로고    scopus 로고
    • Phosphorothioate substitution can substantially alter RNA conformation
    • Smith,J.S. and Nikonowicz,E.P. (2000) Phosphorothioate substitution can substantially alter RNA conformation. Biochemistry, 39, 5642-652.
    • (2000) Biochemistry , vol.39 , pp. 5642-5652
    • Smith, J.S.1    Nikonowicz, E.P.2
  • 18
    • 41849144485 scopus 로고    scopus 로고
    • Brünger,A.T, 1993 X-PLOR Version 3.1: A System for X-ray Crystallography and NMR. Yale Untiversity Press, New Haven
    • Brünger,A.T. (1993) X-PLOR Version 3.1: A System for X-ray Crystallography and NMR. Yale Untiversity Press, New Haven.
  • 21
    • 0024058085 scopus 로고    scopus 로고
    • (1088) The definition of generalized helicoidal parameters and of axis curvature for irregular nucleic acids
    • Lavery,R. and Sklenar,H. (1088) The definition of generalized helicoidal parameters and of axis curvature for irregular nucleic acids. J. Biomol. Struct. Dyn., 6, 63-91.
    • J. Biomol. Struct. Dyn , vol.6 , pp. 63-91
    • Lavery, R.1    Sklenar, H.2
  • 22
    • 0242396923 scopus 로고    scopus 로고
    • 3DNA: A software package for the analysis, rebuilding and visualization of three-dimensional nucleic acid structures
    • Lu,X.J. and Olson, W.K. (2003) 3DNA: A software package for the analysis, rebuilding and visualization of three-dimensional nucleic acid structures. Nucleic Acids Res., 31, 5108-5121.
    • (2003) Nucleic Acids Res , vol.31 , pp. 5108-5121
    • Lu, X.J.1    Olson, W.K.2
  • 23
    • 0029665675 scopus 로고    scopus 로고
    • Solution structures of DNA duplexes containing a DNA × RNA hybrid region, d(GG)r(AGAU)d(GAC) × d(GTCATCT(C) and d(CGGAGA)r(UGAC) × d(GTCATCTCC)
    • Nishizaki,T., Iwai,S., Ohkubo,T., Kojima,C., Nakamura,H., Kyogoku,Y. and Ohtsuka,E. (1996) Solution structures of DNA duplexes containing a DNA × RNA hybrid region, d(GG)r(AGAU)d(GAC) × d(GTCATCT(C) and d(CGGAGA)r(UGAC) × d(GTCATCTCC). Biochemistry, 35, 4016-4025.
    • (1996) Biochemistry , vol.35 , pp. 4016-4025
    • Nishizaki, T.1    Iwai, S.2    Ohkubo, T.3    Kojima, C.4    Nakamura, H.5    Kyogoku, Y.6    Ohtsuka, E.7
  • 25
    • 49349134796 scopus 로고
    • Conformations of nucleosides and nucleotides
    • Davies,D.B. (1978) Conformations of nucleosides and nucleotides. Prog. Nucl. Magn. Reson. Spectrosc., 12, 135-225.
    • (1978) Prog. Nucl. Magn. Reson. Spectrosc , vol.12 , pp. 135-225
    • Davies, D.B.1
  • 26
    • 0022773567 scopus 로고
    • Solution structure of d-GAATTCGAATTC by 2D NMR. A new approach to determination of sugar geometries in DNA segments
    • Hosur,R.V., Ravikumar,M., Chary,K.V.R., Sheth,A, Govil,G., Zu-Kun,T. and Miles,H.T. (1986) Solution structure of d-GAATTCGAATTC by 2D NMR. A new approach to determination of sugar geometries in DNA segments. FEBS Lett., 205, 71-76.
    • (1986) FEBS Lett , vol.205 , pp. 71-76
    • Hosur, R.V.1    Ravikumar, M.2    Chary, K.V.R.3    Sheth, A.4    Govil, G.5    Zu-Kun, T.6    Miles, H.T.7
  • 27
    • 20444483055 scopus 로고
    • The relationship between proton-proton NMR coupling constants and substituent electronegativities-I: 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-I: 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
    • 84988109709 scopus 로고
    • Nucleic acids and nuclear magnetic resonance
    • Van de Ven,F.J. and Hilbers,C.W. (1988) Nucleic acids and nuclear magnetic resonance. Eur. J. Biochem., 178, 1-38.
    • (1988) Eur. J. Biochem , vol.178 , pp. 1-38
    • Van de Ven, F.J.1    Hilbers, C.W.2
  • 29
    • 0026696172 scopus 로고
    • Determination of nucleic acid backbone conformation by 1H NMR
    • Kim,S.G., Lin,L.J. and Reid,B.R. (1992) Determination of nucleic acid backbone conformation by 1H NMR. Biochemistry, 31, 3564-3574.
    • (1992) Biochemistry , vol.31 , pp. 3564-3574
    • Kim, S.G.1    Lin, L.J.2    Reid, B.R.3
  • 30
  • 32
    • 0001440712 scopus 로고    scopus 로고
    • Determination of the Conformations of Nucleic Acids by Electronic CD
    • Fasman,G.D, ed, Plenum Press, NY, pp
    • Johnson,C.W. Jr. (1996) Determination of the Conformations of Nucleic Acids by Electronic CD. In Fasman,G.D. (ed). Circular Dichroism and the Conformational Analysis of Biomolecules, Plenum Press, NY, pp. 433-468.
    • (1996) Circular Dichroism and the Conformational Analysis of Biomolecules , pp. 433-468
    • Johnson Jr., C.W.1
  • 33
    • 0020692923 scopus 로고
    • Ordered wattr structure around a B-DNA dodecamer. A quaatitative study
    • Kopka,M.L., Fratini,A.V., Drew,H.R. and Dickerson,R.E. (1983), Ordered wattr structure around a B-DNA dodecamer. A quaatitative study. J. Mol. Biol., 163, 129-146.
    • (1983) J. Mol. Biol , vol.163 , pp. 129-146
    • Kopka, M.L.1    Fratini, A.V.2    Drew, H.R.3    Dickerson, R.E.4
  • 34
    • 0016299918 scopus 로고
    • Structural details of double-helix observed for DNAs containing alternating purine and pyrimidine sequences
    • Arnottt,S., Chandrasekaran,R., Hukins,D.W., Smith,P.J. and Watts,L. (1974) Structural details of double-helix observed for DNAs containing alternating purine and pyrimidine sequences. J. Mol. Biol., 15 523-533.
    • (1974) J. Mol. Biol , vol.15 , pp. 523-533
    • Arnottt, S.1    Chandrasekaran, R.2    Hukins, D.W.3    Smith, P.J.4    Watts, L.5
  • 36
    • 0042908606 scopus 로고    scopus 로고
    • NMR conformatiohal study reveals that S-C-N anomeric effect in thionucleosides is weaker than O-C-N anomeric effect in natural nucleosides
    • Crnugelj,M. and Plavec,J. (2001) NMR conformatiohal study reveals that S-C-N anomeric effect in thionucleosides is weaker than O-C-N anomeric effect in natural nucleosides. Croatica Chim. Acta., 74, 381-398.
    • (2001) Croatica Chim. Acta , vol.74 , pp. 381-398
    • Crnugelj, M.1    Plavec, J.2
  • 37
    • 0023046565 scopus 로고
    • CD spectra and some properties of deoxyoligonucleotide duplexes having a CG terminus (nucleosides and nucleotides. Part 69)
    • Sato,M., Ono,A., Higuchi,H. and Ueda,F. (1986) CD spectra and some properties of deoxyoligonucleotide duplexes having a CG terminus (nucleosides and nucleotides. Part 69). Nucleic Acids Res., 14 1405-1416.
    • (1986) Nucleic Acids Res , vol.14 , pp. 1405-1416
    • Sato, M.1    Ono, A.2    Higuchi, H.3    Ueda, F.4
  • 40
    • 0019790241 scopus 로고
    • Mapping tRNA structure in solutiod using double-strand-specific ribonuclease VI from cobra venom
    • Lockard,R.E. and Kumar,A. (1981) Mapping tRNA structure in solutiod using double-strand-specific ribonuclease VI from cobra venom. Nucleic Acids Res., 9, 5125-5140.
    • (1981) Nucleic Acids Res , vol.9 , pp. 5125-5140
    • Lockard, R.E.1    Kumar, A.2
  • 41
    • 0020442509 scopus 로고
    • Comparison of transfer ribonucleic acid structures using cobra venom and S1 endonucleases
    • Auron,P.E., Weber,L.D. and Rich,A. (1982) Comparison of transfer ribonucleic acid structures using cobra venom and S1 endonucleases. Biochemistry, 21, 4700-4706.
    • (1982) Biochemistry , vol.21 , pp. 4700-4706
    • Auron, P.E.1    Weber, L.D.2    Rich, A.3
  • 42
    • 0024425738 scopus 로고
    • Deoxynucleotide-containing oligoribonucleotide duplexes: Stability and susceptibility to RNase VI and RNase H
    • Wyatt,J.R. and Walker,G.T. (1989) Deoxynucleotide-containing oligoribonucleotide duplexes: Stability and susceptibility to RNase VI and RNase H. Nucleic Acids Res., 17, 7833-7942.
    • (1989) Nucleic Acids Res , vol.17 , pp. 7833-7942
    • Wyatt, J.R.1    Walker, G.T.2


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