Nucleosides and nucleotides. 184. Synthesis and conformational investigation of anti-fixed 3-deaza-3-halopurine ribonucleosides

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 7158-7172

  Minakawa, Noriaki ^a   Kojima, Naoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMO 3 DEAZAADENOSINE; 3 BROMO 3 DEAZAGUANOSINE; 3 BROMO 3 DEAZAINOSINE; 3 CHLORO 3 DEAZAADENOSINE; 3 CHLORO 3 DEAZAGUANOSINE; 3 CHLORO 3 DEAZAINOSINE; 3 DEAZA 3 FLUOROADENOSINE; 3 DEAZA 3 FLUOROGUANOSINE; 3 DEAZA 3 FLUOROINOSINE; 3 DEAZA 3 IODOADENOSINE; 3 DEAZA 3 IODOINOSINE; PURINE NUCLEOSIDE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; IODINATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033578807     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990638x     Document Type: Article

References (56)

1. Part 183: Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385-388.
2. Purine numbering has been used for all nucleosides throughout the text except for the Experimental Section.
3. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984; pp 51-81.
4. Yoshimura, Y.; Otter, B. A.; Ueda, T.; Matsuda, A. Chem. Pharm. Bull. 1992, 40, 1761-1769 and references therein.
5. For examples: (a) Parkanyi, L.; Kalman, A.; Czugler, M.; Walker, R. T. Nucleic Acids Res. 1987, 15, 4111-4121. (b) Rodriguez, J. B.; Marquez, V. E.; Mitsuya, H.; Barchi, J. J. J. Med. Chem. 1994, 37, 3389-3399. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739-3747.
6. For examples: (a) Parkanyi, L.; Kalman, A.; Czugler, M.; Walker, R. T. Nucleic Acids Res. 1987, 15, 4111-4121. (b) Rodriguez, J. B.; Marquez, V. E.; Mitsuya, H.; Barchi, J. J. J. Med. Chem. 1994, 37, 3389-3399. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739-3747.
7. For examples: (a) Parkanyi, L.; Kalman, A.; Czugler, M.; Walker, R. T. Nucleic Acids Res. 1987, 15, 4111-4121. (b) Rodriguez, J. B.; Marquez, V. E.; Mitsuya, H.; Barchi, J. J. J. Med. Chem. 1994, 37, 3389-3399. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med. Chem. 1996, 39, 3739-3747.
8. Tavale, S. S.; Sobell, H. M. J. Mol. Biol. 1970, 48, 109-123.
9. Abdallah, M. A.; Biellmann, J. F.; Nordstrom, B.; Branden, C. I. Eur. J. Biochem. 1975, 50, 475-481.
10. Iimori, T.; Murai, Y.; Ohuchi, S.; Kodama, Y.; Ohtsuka, Y.; Oishi, T. Tetrahedron Lett. 1991, 32, 7273-7276.
11. (a) Aoyagi, M.; Minakawa, N.; Matsuda, A. Tetrahedron Lett. 1993, 34, 103-106. (b) Yamagata, Y.; Kato, M.; Fujii, S.; Aoyagi, M.; Minakawa, N.; Matsuda, A. Nucleosides Nucleotides 1994, 13, 1327-1335.
12. (a) Aoyagi, M.; Minakawa, N.; Matsuda, A. Tetrahedron Lett. 1993, 34, 103-106. (b) Yamagata, Y.; Kato, M.; Fujii, S.; Aoyagi, M.; Minakawa, N.; Matsuda, A. Nucleosides Nucleotides 1994, 13, 1327-1335.
13. Coincident with our report, Acevedo et al. reported the synthesis of 2′-deoxy-3-alkyl(aryl)-3-deazaguanosines. They indicated that a bulky substituent such as a 1-naphthylethyl group forces the sugar puckering into an unusual C3′-endo conformation, although the nucleoside prefers the anti conformation; see: Acevedo, O. L.; Andrews, R. S.; Cook, P. D. Nucleosides Nucleotides 1993, 12, 403-416.
14. Minakawa, N.; Kojima, N.; Matsuda, A. Heterocycles 1996, 42, 149-154.
15. Minakawa, N.; Takeda, T.; Sasaki, T.; Matsuda, A.; Ueda, T. J. Med. Chem. 1991, 34, 778-786.
16. Minakawa, N.; Matsuda, A. Tetrahedron 1993, 49, 557-570.
17. Unlike the reaction with 2, the reaction mixture immediately turned dark brown and the reaction gave a complex mixture. Although purification and identification were unsuccessful, the byproducts appeared to be polychlorinated 3-deazaadenosine derivatives.
18. 2 at -20 °C gave the desired 3-deaza-3-iodoguanosine derivative, the product was unstable and gave a complex mixture including 18 under usual storage conditions.
19. For review articles, see: (a) Purrington, S. T.; Kagan, B. S.; Patrick, T. B. Chem. Rev. 1986, 86, 997-1018. (b) Wilkinson, J. A. Chem. Rev. 1992, 92, 505-515. Rozen, S. Chem. Rev. 1998, 96, 1717-1736. Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755.
20. For review articles, see: (a) Purrington, S. T.; Kagan, B. S.; Patrick, T. B. Chem. Rev. 1986, 86, 997-1018. (b) Wilkinson, J. A. Chem. Rev. 1992, 92, 505-515. Rozen, S. Chem. Rev. 1998, 96, 1717-1736. Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755.
21. For review articles, see: (a) Purrington, S. T.; Kagan, B. S.; Patrick, T. B. Chem. Rev. 1986, 86, 997-1018. (b) Wilkinson, J. A. Chem. Rev. 1992, 92, 505-515. Rozen, S. Chem. Rev. 1998, 96, 1717-1736. Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755.
22. For review articles, see: (a) Purrington, S. T.; Kagan, B. S.; Patrick, T. B. Chem. Rev. 1986, 86, 997-1018. (b) Wilkinson, J. A. Chem. Rev. 1992, 92, 505-515. Rozen, S. Chem. Rev. 1998, 96, 1717-1736. Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755.
23. Commercially available N-fluoro-3,5-dichloropyridinium triflate, N-fluoropyridinium tetrafluoroborate, and N-fluoro-2,6-dichloropyridinium tetrafluoroborate were examined for direct fluorination.
24. Baillargeon, V. P.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 452-461.
25. Minakawa, N.; Kojima, N.; Matsuda, A. Unpublished work.
26. Rousseau, R. J.; Townsend, L. B.; Robins, R. K. Biochemistry 1966, 5, 756-760.
27. 3 and DMF in 94% yield.
28. Nair, V.; Chamberlain, S. D. Synthesis 1984, 401-403.
29. Seela, F.; Rosemeyer, H.; Fischer, S. Helv. Chim. Acta 1990, 73, 1602-1611.
30. a values of all nucleosides were measured by a slight modification of the method reported by Shugar and Fox. A 0.2 M NaCl solution was used for all pH ranges instead of buffers; see: Shugar, D.; Fox, J. J. Biochim. Biophys. Acta 1952, 9, 199-218.
31. a values of substituted phenols are 9.95 (phenol), 9.28 (m-F), 9.02 (m-Cl), 9.11 (m-Br), and 9.17 (m-I), respectively. This trend is explained in terms of electron-donating effect of fluorine; see: Modena, G.; Scorrano, G. In The Chemistry of The Carbon-halogen Bond, Part 1; Patai, S., Ed.; John Wiley & Sons Ltd.: New York, 1973; Chapter 6, pp 301-406.
32. For examples of conformational studies on the syn/anti equilibrium, see: (a) Davis, J. P.; Hart, P. A. Tetrahedron 1972, 28, 2883-2891. (b) Stolarski, R.; Dudycz, L.; Shugar, D. Eur. J. Biochem. 1980, 108, 111-121. Stolarski, B.; Hagberg, C.; Shugar, D. Eur. J. Biochem. 1984, 138, 187-192. Davies, D. B.; Rajani, P.; Sadikot, H. J. Chem. Soc., Perkin Trans. 2 1985, 279-285. (e) Rosemeyer, H.; Toth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H. P.; Seela, F. J. Org. Chem. 1990, 55, 5784-5790. (f) Cho, B. P.; Evans, F. E. Biochem. Biophys. Res. Commun. 1991, 180, 273-278.
33. For examples of conformational studies on the syn/anti equilibrium, see: (a) Davis, J. P.; Hart, P. A. Tetrahedron 1972, 28, 2883-2891. (b) Stolarski, R.; Dudycz, L.; Shugar, D. Eur. J. Biochem. 1980, 108, 111-121. Stolarski, B.; Hagberg, C.; Shugar, D. Eur. J. Biochem. 1984, 138, 187-192. Davies, D. B.; Rajani, P.; Sadikot, H. J. Chem. Soc., Perkin Trans. 2 1985, 279-285. (e) Rosemeyer, H.; Toth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H. P.; Seela, F. J. Org. Chem. 1990, 55, 5784-5790. (f) Cho, B. P.; Evans, F. E. Biochem. Biophys. Res. Commun. 1991, 180, 273-278.
34. For examples of conformational studies on the syn/anti equilibrium, see: (a) Davis, J. P.; Hart, P. A. Tetrahedron 1972, 28, 2883-2891. (b) Stolarski, R.; Dudycz, L.; Shugar, D. Eur. J. Biochem. 1980, 108, 111-121. Stolarski, B.; Hagberg, C.; Shugar, D. Eur. J. Biochem. 1984, 138, 187-192. Davies, D. B.; Rajani, P.; Sadikot, H. J. Chem. Soc., Perkin Trans. 2 1985, 279-285. (e) Rosemeyer, H.; Toth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H. P.; Seela, F. J. Org. Chem. 1990, 55, 5784-5790. (f) Cho, B. P.; Evans, F. E. Biochem. Biophys. Res. Commun. 1991, 180, 273-278.
35. For examples of conformational studies on the syn/anti equilibrium, see: (a) Davis, J. P.; Hart, P. A. Tetrahedron 1972, 28, 2883-2891. (b) Stolarski, R.; Dudycz, L.; Shugar, D. Eur. J. Biochem. 1980, 108, 111-121. Stolarski, B.; Hagberg, C.; Shugar, D. Eur. J. Biochem. 1984, 138, 187-192. Davies, D. B.; Rajani, P.; Sadikot, H. J. Chem. Soc., Perkin Trans. 2 1985, 279-285. (e) Rosemeyer, H.; Toth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H. P.; Seela, F. J. Org. Chem. 1990, 55, 5784-5790. (f) Cho, B. P.; Evans, F. E. Biochem. Biophys. Res. Commun. 1991, 180, 273-278.
36. For examples of conformational studies on the syn/anti equilibrium, see: (a) Davis, J. P.; Hart, P. A. Tetrahedron 1972, 28, 2883-2891. (b) Stolarski, R.; Dudycz, L.; Shugar, D. Eur. J. Biochem. 1980, 108, 111-121. Stolarski, B.; Hagberg, C.; Shugar, D. Eur. J. Biochem. 1984, 138, 187-192. Davies, D. B.; Rajani, P.; Sadikot, H. J. Chem. Soc., Perkin Trans. 2 1985, 279-285. (e) Rosemeyer, H.; Toth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H. P.; Seela, F. J. Org. Chem. 1990, 55, 5784-5790. (f) Cho, B. P.; Evans, F. E. Biochem. Biophys. Res. Commun. 1991, 180, 273-278.
37. For examples of conformational studies on the syn/anti equilibrium, see: (a) Davis, J. P.; Hart, P. A. Tetrahedron 1972, 28, 2883-2891. (b) Stolarski, R.; Dudycz, L.; Shugar, D. Eur. J. Biochem. 1980, 108, 111-121. Stolarski, B.; Hagberg, C.; Shugar, D. Eur. J. Biochem. 1984, 138, 187-192. Davies, D. B.; Rajani, P.; Sadikot, H. J. Chem. Soc., Perkin Trans. 2 1985, 279-285. (e) Rosemeyer, H.; Toth, G.; Golankiewicz, B.; Kazimierczuk, Z.; Bourgeois, W.; Kretschmer, U.; Muth, H. P.; Seela, F. J. Org. Chem. 1990, 55, 5784-5790. (f) Cho, B. P.; Evans, F. E. Biochem. Biophys. Res. Commun. 1991, 180, 273-278.
38. For examples of conformational studies of the ribose conformer, see: (a) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344. (b) Davies, D. B.; Danyluk, S. S. Biochemistry 1974, 13, 4417-4434. Yokoyama, S.; Yamaizumi, Z.; Nishimura, S.; Miyazawa, T. Nucleic Acids Res. 1979, 6, 2611-2626.
39. For examples of conformational studies of the ribose conformer, see: (a) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344. (b) Davies, D. B.; Danyluk, S. S. Biochemistry 1974, 13, 4417-4434. Yokoyama, S.; Yamaizumi, Z.; Nishimura, S.; Miyazawa, T. Nucleic Acids Res. 1979, 6, 2611-2626.
40. For examples of conformational studies of the ribose conformer, see: (a) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344. (b) Davies, D. B.; Danyluk, S. S. Biochemistry 1974, 13, 4417-4434. Yokoyama, S.; Yamaizumi, Z.; Nishimura, S.; Miyazawa, T. Nucleic Acids Res. 1979, 6, 2611-2626.
41. For examples, see: (a) Slomp, G.; McGarvey, B. R. J. Am. Chem. Soc. 1959, 81, 2200-2201. (b) Nagata, W.; Terasawa, T.; Tori, K. J. Am. Chem. Soc. 1964, 86, 3746-3749. Arnold, D. R.; Trecker, D. J.; Whipple, E. B. J. Am. Chem. Soc. 1965, 87, 2596-2602. (d) Winstein, S.; Carter, P.; Anet, F. A. L.; Bourn, A. J. R. J. Am. Chem. Soc. 1965, 87, 5247-5249.
42. For examples, see: (a) Slomp, G.; McGarvey, B. R. J. Am. Chem. Soc. 1959, 81, 2200-2201. (b) Nagata, W.; Terasawa, T.; Tori, K. J. Am. Chem. Soc. 1964, 86, 3746-3749. Arnold, D. R.; Trecker, D. J.; Whipple, E. B. J. Am. Chem. Soc. 1965, 87, 2596-2602. (d) Winstein, S.; Carter, P.; Anet, F. A. L.; Bourn, A. J. R. J. Am. Chem. Soc. 1965, 87, 5247-5249.
43. For examples, see: (a) Slomp, G.; McGarvey, B. R. J. Am. Chem. Soc. 1959, 81, 2200-2201. (b) Nagata, W.; Terasawa, T.; Tori, K. J. Am. Chem. Soc. 1964, 86, 3746-3749. Arnold, D. R.; Trecker, D. J.; Whipple, E. B. J. Am. Chem. Soc. 1965, 87, 2596-2602. (d) Winstein, S.; Carter, P.; Anet, F. A. L.; Bourn, A. J. R. J. Am. Chem. Soc. 1965, 87, 5247-5249.
44. For examples, see: (a) Slomp, G.; McGarvey, B. R. J. Am. Chem. Soc. 1959, 81, 2200-2201. (b) Nagata, W.; Terasawa, T.; Tori, K. J. Am. Chem. Soc. 1964, 86, 3746-3749. Arnold, D. R.; Trecker, D. J.; Whipple, E. B. J. Am. Chem. Soc. 1965, 87, 2596-2602. Winstein, S.; Carter, P.; Anet, F. A. L.; Bourn, A. J. R. J. Am. Chem. Soc. 1965, 87, 5247-5249.
45. (e) Cheney, B. V. J. Am. Chem. Soc. 1968, 90, 5386-5390.
46. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
47. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
48. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
49. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
50. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
51. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
52. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
53. For examples, see: (a) Schaefer, T.; Reynolds, W. F.; Yonemono, T. Can. J. Chem. 1963, 41, 2969-2976. (b) Yonemoto, T. Can. J. Chem. 1966, 44, 223-231. De Coen, J. L.; Elefante, G.; Liquori, A. M.; Damiani, A. Nature 1967, 216, 910-913. Castellano, S.; Sun, C.; Kostelnik, R. Tetrahedron Lett. 1967, 51, 5205-5209. (e) Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689-1714. (f) Rummens, F. H. A. NMR: Basic Princ. Prog. 1975, 10, 118pp. (g) Bohr, J. E.; Hunt, K. L. C. J. Chem. Phys. 1987, 86, 5441-5448. Cheney, B. V.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 5386-5390.
54. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. In Spectrometric Identification of Organic Compounds, 4th Ed.; John Wiley & Sons: New York, 1981; pp 264-266.
55. Golankiewicz, B.; Ostrowski, T.; Folkman, W. Nucleic Acids Res. 1990, 18, 4779-4782.
56. Van de Ven, F. J. M.; Hilbers, C. W. Eur. J. Biochem. 1988, 178, 1-38.