Probing the molecular interaction of chymotrypsin with organophosphorus compounds by 31P diffusion NMR in aqueous solutions

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 309-314

  Segev, Omri ^a,b   Columbus, Ishay ^b   Ashani, Yacov ^b   Cohen, Yoram ^a  

^a TEL AVIV UNIVERSITY   (Israel)

^b ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; SOLUTIONS;

CHYMOTRYPSIN; MOLECULAR INTERACTIONS; ORGANOPHOSPHORUS COMPOUNDS;

DIFFUSION;

1 PYRENEBUTYL PHOSPHORODICHLORIDATE; CHYMOTRYPSIN; CHYMOTRYPSIN A; DYFLOS; ORGANOPHOSPHORUS COMPOUND; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATE; DEALKYLATION; DIFFUSION; DIFFUSION COEFFICIENT; HYDROLYSIS; MOLECULAR INTERACTION; MOLECULAR PROBE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; THERMOSTABILITY;

ANIMALS; CATTLE; CHYMOTRYPSIN; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS;

EID: 11844269215     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0485942     Document Type: Article

References (70)

1. (a) Hartley, B. S. Annu. Rev. Biochem. 1960, 29, 45-49.
2. (b) Aldrich, W. N.; Reiner, E. In Enzyme Inhibitors as Substrates; Neuberger, A., Tatum, E. L., Eds.; North-Holland Publishing Co.: Amsterdam and London, and American Elsevier Publishing: New York, 1972.
3. (a) Cohen, J. A.; Oosterbaan, R. A.; Warringa, M. G. P. J.; Jansz, H. S. Disuss. Faraday Soc. 1955, 20, 114-124.
4. (b) Oosterbaan, R. A.; Kunst, P.; Cohen J. A. Biochim. Biophys. Acta 1955, 16, 299-307.
5. Froede, H. C.; Wilson, I. B. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1971; Vol. 5, pp 87-114.
6. (a) Hobbiger, F. Br. J. Pharmacol. 1965, 14, 73-77.
7. (b) Berends, F.; Postumus, C. H.; Sluys, I. V. D.; Deierkauf, F. A. Biochim. Biophys. Acta 1959, 34, 576-578.
8. (a) Michel, O. H. Fed. Proc., Fed. Am. Soc. Exp. Biol. 1958, 17, 275-283.
9. (b) Berends, F.; Postumus, C. H.; Sluys, I. V. D.; Deierkauf, F. A. Biochim. Biophys. Acta 1959, 34, 576-578.
10. (c) Sun, M.; Chang, Z.; Shau, M.; Huang, R.; Chou, T. Eur. J. Biochem. 1979, 100, 527-530.
11. (a) Stroud, R. M.; Kay, L. M.; Dickerson, R. E. J. Mol. Biol. 1974, 83, 185-208.
12. (b) Cohen, J. H.; Silverton, E. W.; Davies, D. R. J. Mol. Biol. 1981, 148, 449-479.
13. (c) Ringe, D.; Mottonen, J. M.; Gelb, M. H.; Abeles, R. H. Biochemistry. 1986, 25, 5633-5638.
14. (d) Harel, M.; Su, C. T.; Frolow, F.; Ashani, Y.; Silman, I.; Sussman, J. L. J. Mol. Biol. 1991, 221, 909-918.
15. (e) Millard, C. B.; Kryger, G.; Ordentlich, A.; Greenblat, H. M.; Harel, M.; Raves, M. L.; Segall, Y.; Barak, D.; Shafferman, A.; Silman, I.; Sussman, J. L. Biochemistry 1999, 38, 7032-7039.
16. (f) Millard, C. B.; Koellner, G.; Ordentlich, A.; Shafferman, A.; Silman, I.; Sussman, J. L. J. Am. Chem. Soc. 1999, 121, 9883-9884.
17. Kossiakoff, A. A.; Spencer, S. A. Nature (London) 1980, 288, 414-416
18. (a) Viragh, C.; Harris, T. K.; Reddy, P. M.; Massiah, M. A.; Mildvan, A. S.; Kovach, I. M. Biochemistry 2000, 39, 16200-16205.
19. (b) Messiah, M. A.; Viragh, C.; Reddy, P. M.; Kovach, I. M.; Johnson, J.; Rossenberry, T. L.; Mildvan, A. S. Biochemistry 2001, 40, 5682-5690
20. (a) Gorenstein, D. G.; Findlay, J. B. Biochem. Biophys. Res. Commun. 1976, 72, 640-645.
21. (b) van Der Drift, A. C. M.; Beck, H. C.; Dekker: W. H.; Hulst, A. G.; Wils, E. R. J. Biochemistry. 1985, 24, 6894-6903.
22. (c) Gorenstein, D. G.; Shah, D.; Chen, R.; Kallick, D. Biochemistry. 1989, 28, 2050-2058.
23. (d) Grunwald, J.; Segall, Y.; Shirin, E.; Waysbort, D.; Steinberg, N.; Silman, I.; Ashani, Y. Biochem. Pharmacol. 1989, 19, 3157-3168.
24. (e) Oleksyszyn, J.; Powers, J. C.; Biochemistry 1991, 30, 485-493.
25. (f) Kovach, I. M.; Mckay, L.; Vander Velde, D. Chirality 1993, 5, 143-149.
26. (g) Segall, Y.; Waysbort, D.; Barak, D.; Ariel, N.; Doctor, B. P.; Grunwald, J.; Ashani, Y. Biochemistry. 1993, 32, 13441-13450.
27. (a) Stejskal, E. O.; Tanner, J. E. J. Chem. Phys. 1965, 42, 288-292.
28. (b) Tanner, J. E. J. Chem. Phys. 1970, 52, 2523-2526.
29. For reviews concerning the application of the pulsed-gradient NMR techniques to different systems see: c) Stilbs, P. Prog. NMR Spectrosc. 1987, 19, 1-45. (d) Price, W. S. Concepts Magn. Reson. 1997, 9, 299-336. (e) Johnson, C. S., Jr. Prog. NMR Spectrosc. 1999, 34, 203-256.
30. For reviews concerning the application of the pulsed-gradient NMR techniques to different systems see: c) Stilbs, P. Prog. NMR Spectrosc. 1987, 19, 1-45. (d) Price, W. S. Concepts Magn. Reson. 1997, 9, 299-336. (e) Johnson, C. S., Jr. Prog. NMR Spectrosc. 1999, 34, 203-256.
31. For reviews concerning the application of the pulsed-gradient NMR techniques to different systems see: c) Stilbs, P. Prog. NMR Spectrosc. 1987, 19, 1-45. (d) Price, W. S. Concepts Magn. Reson. 1997, 9, 299-336. (e) Johnson, C. S., Jr. Prog. NMR Spectrosc. 1999, 34, 203-256.
32. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
33. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
34. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
35. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
36. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
37. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
38. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
39. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
40. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
41. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
42. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
43. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
44. For a few selected examples, see: (a) Rymdén, R.; Carlfors, J.; Stilbs, P. J. Inclusion Phenom. 1983, 1, 159-167. (b) Mayzel, O.; Cohen, Y. J. Chem. Soc., Chem. Commun. 1994, 1901-1902. (c) Cohen, Y.; Ayalon, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 816-818. (d) Mayzel, O.; Gafni, A.; Cohen, Y. Chem. Commun. 1996, 911-912. (e) Gafni, A.; Cohen, Y. J. Org. Chem. 1997, 62, 120-125. (f) Cameron, K. S.; Fielding, L. J. Org. Chem. 2001, 66, 6891-6895. (g) Pochapsky, S. S.; Mo, H.; Pochapsky, T. C. J. Chem. Soc., Chem. Commun. 1995, 2513-2514. (h) Mo, H.; Pochapsky, T. C. J. Phys. Chem. B 1997, 101, 4485-4486. (i) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A. Organometallics 2000, 19, 4663-4665. (j) Valentini, M.; Rügger, H.; Pregosin, P. S. Helv. Chim. Acta 2001, 84, 2833-2853. (k) Avram, L.; Cohen, Y. J. Org. Chem. 2002, 67, 2639-2644. (l) Hori, A.; Kumazawa, K.; Kusukawa, T.; Chand, D. K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Chem. Eur. J. 2001, 7, 4142-4149. (m) Kotch, F. W.; Sidorov V.; Lam Y.-F.; Kayser K. J.; Hojun L.; Kaucher M. S.; Davis J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
45. (a) Frish, L.; Matthews, S. E.; Böhmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 1999, 669-671.
46. (b) Frish, L.; Vysotsky, M. O.; Matthews, S. E.; Böhmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 2002, 88-93.
47. (c) Frish, L.; Vysotsky, M. O.; Böhmer, V.; Cohen, Y. Org. Biomol. Chem. 2003, 1, 2011-2014.
48. (a) Avram, L.; Cohen, Y. J. Am. Chem. Soc. 2002, 124, 15148-15149.
49. (b) Avram, L.; Cohen, Y. Org. Lett. 2002, 4, 4365-4368.
50. (c) Avram, L.; Cohen, Y. Org. Lett. 2003, 5, 3329-3332.
51. (d) Avram, L.; Cohen, Y. J. Am. Chem. Soc. 2003, 125, 16180-16181.
52. (a) Jones, J. A.; Wilkins, D. K.; Smith, L. J.; Dobson, C. M. J. Biomol. NMR 1997, 10, 199-203.
53. (b) Mansfield, S. L.; Jayawickrama, D. A.; Timmons, J. S.; Larive, C. K. Biochim. Biophys. Acta 1998, 1382, 257-265.
54. (c) Zhang, W.; Smithgall, T. E.; Gmeiner, W. H. Biochemistry 1998, 37, 7119-7126.
55. (d) Price, W. S.; Tsuchiya, F.; Arata, Y. J. Am. Chem. Soc. 1999, 121, 11503-1151.
56. (e) Chang, X.; Keller, D.; O'Donoghue, S. I.; Led, J. J. FEBS. Lett. 2002, 515, 165-170.
57. (f) Weljie, A. M.; Yamniuk, A. P.; Yoshino, H.; Izumi, Y.; Vogel, H. J. Protein Sci. 2003, 12, 228-236.
58. (a) Lapham, J.; Rife, J. P.; Moore, P. B.; Crothers, D. M. J. Biomol. NMR 1997, 10, 255-262.
59. (b) Gmeiner, W. H.; Hudalla, C. J.; Soto, A. M.; Marky, L. FEBS. Lett. 2000, 465, 148-152.
60. (c) Yang, X.; Sanghvi, Y. S.; Gao, X. J. Biomol. NMR 1997, 10, 383-388.
61. Delmar, E. G.; Largman, C.; Brodrick, J. W.; Geokas, M. C. Anal. Biochem. 1979, 99, 316-320.
62. Cohen, D.; Erlanger, B. F. J. Am. Chem. Soc. 1960, 82, 3928-3934.
63. -1; see: Dingley, A. J.; Mackay, J. P.; Shaw G. L.; Hambly, B. D.; King, G. F. J. Biomol. NMR 1997, 10, 1-8.
64. Dingley, A. J.; Mackay, J. P.; Morris, M. B.; Chapman, B. E.; Kuchel, P. W.; Hambly, B. D.; King, G. F. J. Biomol. NMR 1995, 6, 321-328.
65. Derrik, T. S.; Licas, L. H.; Dimicoli, J.-L.; Larive, C. K. Magn. Reson. Chem. 2002, 40, S98-S115.
66. (a) Lin, M.; Shapiro, M. J.; Wareing, J. R. J. Org. Chem. 1997, 62, 8930-8931.
67. (b) Bleicher, K.; Lin, M.; Shapiro, M. J.; Wareing, J. R. J. Org. Chem. 1998, 63, 8486-8490.
68. (c) Anderson, R. C.; Lin, M.; Shapiro, M. J. J. Comb. Chem. 1999, 1, 69-72.
69. (d) Lin, M.; Shapiro, M. J.; Wareing, J. R. J. Am. Chem. Soc. 1997, 119, 5249-5250;
70. e) Chen, A.; Shapiro, M. J. Anal. Chem. 1999, 71, 669A-675A.