Highly Precise Shape Mimicry by a Difluorotoluene Deoxynucleoside, a Replication-Competent Substitute for Thymidine

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 24, 1997, Pages 2825-2828

  Guckian, Kevin M ^a   Kool, Eric T ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

Carbohydrates; Conformation; Hydrogen bonds; Nucleosides; Structure elucidation

Indexed keywords

EID: 0032491819     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199728251     Document Type: Article

References (23)

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4. See also discussions of replication fidelity in current textbooks: a) J. D. Watson, N. H. Hopkins, J. W. Roberts, J. A. Steitz, A. M. Weiner, Molecular Biology of the Gene, 4th ed., Benjamin/Cummings, Menlo Park, 1987, p. 283; b) L. Stryer, Biochemistry, 4th ed., Freeman, New York, 1995, p. 89.
5. See also discussions of replication fidelity in current textbooks: a) J. D. Watson, N. H. Hopkins, J. W. Roberts, J. A. Steitz, A. M. Weiner, Molecular Biology of the Gene, 4th ed., Benjamin/Cummings, Menlo Park, 1987, p. 283; b) L. Stryer, Biochemistry, 4th ed., Freeman, New York, 1995, p. 89.
6. See, for example: a) E. Freese, J. Mol. Biol. 1959, 1, 87; b) L. C. Sowers, G. V. Fazakerley, R. Eritja, B. E. Kaplan, M. F. Goodman, Proc. Natl. Acad. Sci. USA 1986, 83, 5434; c) R. Eritja, D. M. Horowitz, P. A. Walker, J. P. Ziehler-Martin, M. S. Boosalis, M. F. Goodman, K. Itakura, B. E. Kaplan, Nucleic Acids Res. 1986, 14, 8135; d) B. Singer, S. Spengler, Biochemistry 1981, 20, 1127; e) P. Strazewski, C. Tamm, Angew. Chem. 1990, 102, 37; Angew. Chem. Int. Ed. Engl. 1990, 29, 36; f) S. Shibutani, M. Takeshita, A. P. Grollman, Nature 1991, 349, 431; g) D. C. Ward, E. Reich, J. Biol. Chem. 1972, 247, 705.
7. See, for example: a) E. Freese, J. Mol. Biol. 1959, 1, 87; b) L. C. Sowers, G. V. Fazakerley, R. Eritja, B. E. Kaplan, M. F. Goodman, Proc. Natl. Acad. Sci. USA 1986, 83, 5434; c) R. Eritja, D. M. Horowitz, P. A. Walker, J. P. Ziehler-Martin, M. S. Boosalis, M. F. Goodman, K. Itakura, B. E. Kaplan, Nucleic Acids Res. 1986, 14, 8135; d) B. Singer, S. Spengler, Biochemistry 1981, 20, 1127; e) P. Strazewski, C. Tamm, Angew. Chem. 1990, 102, 37; Angew. Chem. Int. Ed. Engl. 1990, 29, 36; f) S. Shibutani, M. Takeshita, A. P. Grollman, Nature 1991, 349, 431; g) D. C. Ward, E. Reich, J. Biol. Chem. 1972, 247, 705.
8. See, for example: a) E. Freese, J. Mol. Biol. 1959, 1, 87; b) L. C. Sowers, G. V. Fazakerley, R. Eritja, B. E. Kaplan, M. F. Goodman, Proc. Natl. Acad. Sci. USA 1986, 83, 5434; c) R. Eritja, D. M. Horowitz, P. A. Walker, J. P. Ziehler-Martin, M. S. Boosalis, M. F. Goodman, K. Itakura, B. E. Kaplan, Nucleic Acids Res. 1986, 14, 8135; d) B. Singer, S. Spengler, Biochemistry 1981, 20, 1127; e) P. Strazewski, C. Tamm, Angew. Chem. 1990, 102, 37; Angew. Chem. Int. Ed. Engl. 1990, 29, 36; f) S. Shibutani, M. Takeshita, A. P. Grollman, Nature 1991, 349, 431; g) D. C. Ward, E. Reich, J. Biol. Chem. 1972, 247, 705.
9. See, for example: a) E. Freese, J. Mol. Biol. 1959, 1, 87; b) L. C. Sowers, G. V. Fazakerley, R. Eritja, B. E. Kaplan, M. F. Goodman, Proc. Natl. Acad. Sci. USA 1986, 83, 5434; c) R. Eritja, D. M. Horowitz, P. A. Walker, J. P. Ziehler-Martin, M. S. Boosalis, M. F. Goodman, K. Itakura, B. E. Kaplan, Nucleic Acids Res. 1986, 14, 8135; d) B. Singer, S. Spengler, Biochemistry 1981, 20, 1127; e) P. Strazewski, C. Tamm, Angew. Chem. 1990, 102, 37; Angew. Chem. Int. Ed. Engl. 1990, 29, 36; f) S. Shibutani, M. Takeshita, A. P. Grollman, Nature 1991, 349, 431; g) D. C. Ward, E. Reich, J. Biol. Chem. 1972, 247, 705.
10. See, for example: a) E. Freese, J. Mol. Biol. 1959, 1, 87; b) L. C. Sowers, G. V. Fazakerley, R. Eritja, B. E. Kaplan, M. F. Goodman, Proc. Natl. Acad. Sci. USA 1986, 83, 5434; c) R. Eritja, D. M. Horowitz, P. A. Walker, J. P. Ziehler-Martin, M. S. Boosalis, M. F. Goodman, K. Itakura, B. E. Kaplan, Nucleic Acids Res. 1986, 14, 8135; d) B. Singer, S. Spengler, Biochemistry 1981, 20, 1127; e) P. Strazewski, C. Tamm, Angew. Chem. 1990, 102, 37; Angew. Chem. Int. Ed. Engl. 1990, 29, 36; f) S. Shibutani, M. Takeshita, A. P. Grollman, Nature 1991, 349, 431; g) D. C. Ward, E. Reich, J. Biol. Chem. 1972, 247, 705.
11. See, for example: a) E. Freese, J. Mol. Biol. 1959, 1, 87; b) L. C. Sowers, G. V. Fazakerley, R. Eritja, B. E. Kaplan, M. F. Goodman, Proc. Natl. Acad. Sci. USA 1986, 83, 5434; c) R. Eritja, D. M. Horowitz, P. A. Walker, J. P. Ziehler-Martin, M. S. Boosalis, M. F. Goodman, K. Itakura, B. E. Kaplan, Nucleic Acids Res. 1986, 14, 8135; d) B. Singer, S. Spengler, Biochemistry 1981, 20, 1127; e) P. Strazewski, C. Tamm, Angew. Chem. 1990, 102, 37; Angew. Chem. Int. Ed. Engl. 1990, 29, 36; f) S. Shibutani, M. Takeshita, A. P. Grollman, Nature 1991, 349, 431; g) D. C. Ward, E. Reich, J. Biol. Chem. 1972, 247, 705.
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20. Close F-H contacts are defined here as contacts ≤2.35 Å [11].
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