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Volumn 39, Issue 19, 1996, Pages 3739-3747

Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides?

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; HETERODUPLEX; NUCLEOSIDE; NUCLEOSIDE DERIVATIVE; OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATE; RIBONUCLEASE H;

EID: 0029815436     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960306+     Document Type: Article
Times cited : (268)

References (33)
  • 2
    • 0015511563 scopus 로고
    • Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. A New Description of Using the Concept of Pseudorotation
    • The concept of pseudorotation was introduced and applied for the first time to substituted furanoses by Altona, C.; Sundaralingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. A New Description of Using the Concept of Pseudorotation. J. Am. Chem. Soc. 1972, 94, 8205-8212.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 8205-8212
    • Altona, C.1    Sundaralingam, M.2
  • 3
    • 0001120142 scopus 로고
    • How do the Gauche and Anomeric Effects Drive the Pseudorotational Equilibrium of the Pentofuranose Moiety of Nucleosides?
    • Plavec, J.; Tong, W.; Chattopadhyaya, J. How do the Gauche and Anomeric Effects Drive the Pseudorotational Equilibrium of the Pentofuranose Moiety of Nucleosides? J. Am. Chem. Soc. 1993, 115, 9734-9746.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9734-9746
    • Plavec, J.1    Tong, W.2    Chattopadhyaya, J.3
  • 4
    • 84985069908 scopus 로고
    • Empirical Correlations between Conformational Parameters in β-D-Furanoside Fragments Derived from a Statistical Survery of Crystal Structures of Nucleic Acid Constituents
    • DeLeeuw, H. P. M.; Haasnoot, C. A. G.; Altona, C. Empirical Correlations Between Conformational Parameters in β-D-Furanoside Fragments Derived from a Statistical Survery of Crystal Structures of Nucleic Acid Constituents. Israel J. Chem. 1980, 20, 108-126.
    • (1980) Israel J. Chem. , vol.20 , pp. 108-126
    • DeLeeuw, H.P.M.1    Haasnoot, C.A.G.2    Altona, C.3
  • 6
    • 0030050588 scopus 로고    scopus 로고
    • Conformationally Constrained Analogues of Diacylglycerol. 10. Ultrapotent Protein Kinase C Ligands Based on a Racemic 5-Disubstituted Tetrahydro-2-furanone Template
    • Sharma, R.; Lee, J.; Wang, S.; Milne, G. W. A.; Lewin, N. E.; Blumberg, P. M.; Marquez, V. E. Conformationally Constrained Analogues of Diacylglycerol. 10. Ultrapotent Protein Kinase C Ligands Based on a Racemic 5-Disubstituted Tetrahydro-2-furanone Template. J. Med. Chem. 1996, 39, 19-28.
    • (1996) J. Med. Chem. , vol.39 , pp. 19-28
    • Sharma, R.1    Lee, J.2    Wang, S.3    Milne, G.W.A.4    Lewin, N.E.5    Blumberg, P.M.6    Marquez, V.E.7
  • 7
    • 0027383216 scopus 로고
    • Synthesis of Cyclopropane-fused Dideoxycarbocyclic Nucleosides Structurally Related to Neplanocin C
    • Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Barchi, J. J., Jr. Synthesis of Cyclopropane-fused Dideoxycarbocyclic Nucleosides Structurally Related to Neplanocin C. Tetrahedron Lett. 1993, 34, 6233-6236.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6233-6236
    • Rodriguez, J.B.1    Marquez, V.E.2    Nicklaus, M.C.3    Barchi Jr., J.J.4
  • 8
    • 0028299975 scopus 로고
    • 4′,6′-Methano Carbocyclic Thymidine: A Conformationally Constrained Building Block for Oligonucleotides
    • Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. 4′,6′-Methano Carbocyclic Thymidine: A Conformationally Constrained Building Block for Oligonucleotides. Tetrahedron Lett. 1994, 35, 2331-2334.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2331-2334
    • Altmann, K.-H.1    Kesselring, R.2    Francotte, E.3    Rihs, G.4
  • 9
    • 0028004592 scopus 로고
    • Conformationally Locked Nucleoside Analogues. Synthesis of Dideoxycarbocyclic Nucleoside Analogues Structurally Related to Neplanocin C
    • Rodriguez, J. B.; Marquez, V. E.; Nicklaus, M. C.; Mitsuya, H.; Barchi, J. J., Jr. Conformationally Locked Nucleoside Analogues. Synthesis of Dideoxycarbocyclic Nucleoside Analogues Structurally Related to Neplanocin C. J. Med. Chem. 1994, 37, 3389-3399.
    • (1994) J. Med. Chem. , vol.37 , pp. 3389-3399
    • Rodriguez, J.B.1    Marquez, V.E.2    Nicklaus, M.C.3    Mitsuya, H.4    Barchi Jr., J.J.5
  • 10
    • 0028090396 scopus 로고
    • 1′,6′-Methano Carbocyclic Thymidine: Synthesis and X-ray Crystal Structure, and Effect on Nucleic Acid Duplex Stability
    • Altmann, K.-H.; Imwinkelried, R.; Kesselring, R.; Rihs, G. 1′,6′-Methano Carbocyclic Thymidine: Synthesis and X-ray Crystal Structure, and Effect on Nucleic Acid Duplex Stability. Tetrahedron Lett. 1994, 35, 7625-7628.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7625-7628
    • Altmann, K.-H.1    Imwinkelried, R.2    Kesselring, R.3    Rihs, G.4
  • 11
    • 0029044137 scopus 로고
    • A Simple Approach to 1,1′a-Methano Carbocyclic Thymidine
    • A full account of this work has been recently submitted to J. Chem. Soc., Perkin Trans. 1
    • Ezzitouni, A.; Barchi, J. J., Jr.; Marquez, V. E. A Simple Approach to 1,1′a-Methano Carbocyclic Thymidine. J. Chem. Soc., Chem. Commun. 1995, 1345-1346. A full account of this work has been recently submitted to J. Chem. Soc., Perkin Trans. 1.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 1345-1346
    • Ezzitouni, A.1    Barchi Jr., J.J.2    Marquez, V.E.3
  • 12
    • 0029923673 scopus 로고    scopus 로고
    • Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxyaristeromycin Built on a Bicyclo[3.1.0]hexane Template
    • Siddiqui, M. A.; Ford, H., Jr.; George, C.; Marquez, V. E. Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxyaristeromycin Built on a Bicyclo[3.1.0]hexane Template. Nucleosides Nucleotides 1996, 15, 235-250.
    • (1996) Nucleosides Nucleotides , vol.15 , pp. 235-250
    • Siddiqui, M.A.1    Ford Jr., H.2    George, C.3    Marquez, V.E.4
  • 13
    • 85077634689 scopus 로고
    • The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
    • Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 15
    • 8944229590 scopus 로고
    • 4-(1,2,4-Triazol-1-yl)- and 4-(3-Nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl) pyrimidin-2(1H)-ones. Valuable Intermediates in the Synthesis of Derivatives of 1-(β-D-Arabinofuranosyl)cyosine (Ara-C)
    • Divakar, K. J.; Reese, C. B. 4-(1,2,4-Triazol-1-yl)- and 4-(3-Nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl) pyrimidin-2(1H)-ones. Valuable Intermediates in the Synthesis of Derivatives of 1-(β-D-Arabinofuranosyl)cyosine (Ara-C). J. Chem. Soc., Perkin Trans. I 1982, 1171-1176.
    • (1982) J. Chem. Soc., Perkin Trans. I , pp. 1171-1176
    • Divakar, K.J.1    Reese, C.B.2
  • 16
    • 9544228962 scopus 로고    scopus 로고
    • note
    • Antiviral testing was performed by Dr. Earl Kern of the University of Alabama at Birmingham and supported by USPHS Contract N01-AI-35177 from the National Institute of Allergy and Infectious Diseases, NIH.
  • 17
    • 0020698514 scopus 로고
    • Carbocyclic Analogues of 5-Substituted Uracil Nucleosides: Synthesis and Antiviral Activity
    • Shealy, Y. F.; O'Dell, C. A.; Shannon, W. M.; Arnett, G. Carbocyclic Analogues of 5-Substituted Uracil Nucleosides: Synthesis and Antiviral Activity. J. Med. Chem. 1983, 26, 156-161.
    • (1983) J. Med. Chem. , vol.26 , pp. 156-161
    • Shealy, Y.F.1    O'Dell, C.A.2    Shannon, W.M.3    Arnett, G.4
  • 18
    • 0022574508 scopus 로고
    • Synthesis and Antiviral Activity of the Carbocyclic Analogues of 5-Ethyl-2′-deoxyuridine and 5-Ethynyl-2′-deoxyuridine
    • Shealy, Y. F.; O'Dell, C. A.; Arnett, G.; Shannon, W. M. Synthesis and Antiviral Activity of the Carbocyclic Analogues of 5-Ethyl-2′-deoxyuridine and 5-Ethynyl-2′-deoxyuridine. J. Med. Chem. 1986, 29, 79-84.
    • (1986) J. Med. Chem. , vol.29 , pp. 79-84
    • Shealy, Y.F.1    O'Dell, C.A.2    Arnett, G.3    Shannon, W.M.4
  • 19
    • 0025271041 scopus 로고
    • Stereospecific Synthesis and Antiviral Properties of Different Enantiomerically Pure Carbocyclic 2′-Deoxyribonucleoside Analogues Derived from Common Chiral Pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one
    • Beres, J.; Sagi, G.; Tomoskozi, I.; Gruber, L.; Baitz-Gacs, E.; Otvos, L.; De Clercq, E. Stereospecific Synthesis and Antiviral Properties of Different Enantiomerically Pure Carbocyclic 2′-Deoxyribonucleoside Analogues Derived from Common Chiral Pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one. J. Med. Chem. 1990, 33, 1353-1360.
    • (1990) J. Med. Chem. , vol.33 , pp. 1353-1360
    • Beres, J.1    Sagi, G.2    Tomoskozi, I.3    Gruber, L.4    Baitz-Gacs, E.5    Otvos, L.6    De Clercq, E.7
  • 20
    • 9544242414 scopus 로고    scopus 로고
    • See ref 1, pp 220-241
    • See ref 1, pp 220-241.
  • 21
    • 0028612005 scopus 로고
    • The A-Form of DNA: In Search of Biological Role
    • Ivanov, V. I.; Minchenkova, L. E. The A-Form of DNA: in Search of Biological Role (a Review). Mol. Biol. 1995, 28, 780-788 (translated from Mol. Biol. 1994, 28, 1258-1271).
    • (1995) Mol. Biol. , vol.28 , pp. 780-788
    • Ivanov, V.I.1    Minchenkova, L.E.2
  • 22
    • 0028612005 scopus 로고
    • Ivanov, V. I.; Minchenkova, L. E. The A-Form of DNA: in Search of Biological Role (a Review). Mol. Biol. 1995, 28, 780-788 (translated from Mol. Biol. 1994, 28, 1258-1271).
    • (1994) Mol. Biol. , vol.28 , pp. 1258-1271
  • 23
  • 26
    • 0027479864 scopus 로고
    • Uniformly Modified 2′-Deoxy-2′-fluoro Phosphorothioate Oligonucleotides as Nuclease-Resistant Antisense Compounds with High Affinity and Specificity for RNA Targets
    • Kawasaki, A. M.; Casper, M. D.; Freier, S. M.; Lesnik, E. A.; Zounes, M. C.; Cummins, L. L.; Gonzalez, C.; Cook, P. D. Uniformly Modified 2′-Deoxy-2′-fluoro Phosphorothioate Oligonucleotides as Nuclease-Resistant Antisense Compounds with High Affinity and Specificity for RNA Targets. J. Med. Chem. 1993, 36, 831-841.
    • (1993) J. Med. Chem. , vol.36 , pp. 831-841
    • Kawasaki, A.M.1    Casper, M.D.2    Freier, S.M.3    Lesnik, E.A.4    Zounes, M.C.5    Cummins, L.L.6    Gonzalez, C.7    Cook, P.D.8
  • 27
    • 0029867162 scopus 로고    scopus 로고
    • Enhanced activity of an antisense oligonucleotide targeting murine protein kinase C-alpha by the incorporation of 2′-O-propyl modifications
    • McKay, R. A.; Cummins, L. L.; Graham, M. J.; Lesnik, E. A.; Owens, S. R.; Winniman, M.; Dean, N. M. Enhanced activity of an antisense oligonucleotide targeting murine protein kinase C-alpha by the incorporation of 2′-O-propyl modifications. Nucleic Acids Res. 1996, 24, 411-417.
    • (1996) Nucleic Acids Res. , vol.24 , pp. 411-417
    • McKay, R.A.1    Cummins, L.L.2    Graham, M.J.3    Lesnik, E.A.4    Owens, S.R.5    Winniman, M.6    Dean, N.M.7
  • 28
    • 9544254553 scopus 로고    scopus 로고
    • See ref 1, pp 9-28
    • See ref 1, pp 9-28.
  • 30
    • 0000614020 scopus 로고
    • The Crystal and Molecular Structure of Thymidine
    • Young, D. W.; Tollin, P.; Wilson, H. R. The Crystal and Molecular Structure of Thymidine. Acta Crystallogr. 1969, B25, 1423-1432.
    • (1969) Acta Crystallogr. , vol.B25 , pp. 1423-1432
    • Young, D.W.1    Tollin, P.2    Wilson, H.R.3
  • 31
    • 0025146530 scopus 로고
    • Crystal and Molecular Structure of (+)-Carba-Thymidine C11H16N2O6
    • Kalman, A.; Koritsanszky, T.; Beres, J.; Sagi, G. Crystal and Molecular Structure of (+)-Carba-Thymidine C11H16N2O6. Nucleosides Nucleotides 1990, 9, 235-243.
    • (1990) Nucleosides Nucleotides , vol.9 , pp. 235-243
    • Kalman, A.1    Koritsanszky, T.2    Beres, J.3    Sagi, G.4


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