Probing the abilities of synthetically useful serine proteases to discriminate remote stereocenters. Chiral naphthyl aldehyde inhibitors

Journal of the American Chemical Society

Volumn 119, Issue 43, 1997, Pages 10260-10268

  Lee, Taekyu ^a   Jones, J Bryan ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHYMOTRYPSIN A; NAPHTHALENE DERIVATIVE; SERINE PROTEINASE; SERINE PROTEINASE INHIBITOR; SUBTILISIN;

ARTICLE; CHIRALITY; DRUG IDENTIFICATION; ENANTIOMER; ENZYME ACTIVITY; IN VITRO STUDY; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030668111     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9708777     Document Type: Article

References (62)

1. (a) Biotransformations in Preparative Organic Chemistry, 2nd ed.; Faber, K., Ed.; Springer-Verlag: New York, 1995.
2. (b) Enzymes in Synthetic Organic Chemistry, Wong, C.-H., Whitesides, G. M., Eds.; Pergamon: New York, 1994.
3. (c) Preparative Biotransformations; Roberts, S. M., Ed.; Wiley: New York, 1993.
4. (a) Hughes, D. L.; Bergan, J. J.; Amato, J. S.; Bhupathy, M.; Leazer, J. L.; McNamara, J. M.; Sidler, D. R.; Reider, P. J.; Grabowski, E. J. J. J. Org. Chem. 1990, 55, 6252.
5. (b) Ladner, W. E.; Whitesides, G. M. J. Am. Chem. Soc. 1984, 106, 7250.
6. (c) Jones, J. B.; Marr, P. W. Tetrahedron Lett. 1973, 3165.
7. (d) Mohr, P.; Waespe-Sarcevic, N.; Tamm, C.; Gawronska, K.; Gawronski, J. K. Helv. Chim. Acta 1983, 66, 2501.
8. (e) Cohen, S. G.; Weinstein, S. Y. J. Am. Chem. Soc. 1964, 86, 725.
9. (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
10. (b) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley: New York, 1994.
11. (c) Asymmetric Synthesis of Natural Products; Koskinen, A., Ed.; Wiley: New York, 1993.
12. (d) Transition Metals in the Synthesis of Complex Organic Molecules; Hegedus, L. S., Ed.; University Science Books: Mill Valley, CA, 1994.
13. (a) Delinck, D. L.; Margolin, A. L. Tetrahedron Lett. 1990, 31, 3093.
14. (b) Pugniere, M.; San Juan, C.; Previero, A. Tetrahedron Lett. 1990, 31, 4883.
15. (c) Gotor, V.; Garcia, M. J.; Rebelleo, F. Tetrahedron Asymmetry 1990, 1, 277.
16. (d) Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849.
17. (e) Chenevert, R.; Desjardins, M.; Gagnon, R. Chem. Lett. 1990, 33.
18. (f) Chenevert, R.; Letourneau, M.; Thiboutot, S. Can. J. Chem. 1990, 960.
19. (h) Frigerio, F.; Coda, A.; Pugliese, L.; Lionetti, C.; Menegatti, E.; Amiconi, G.; Schnebli, H. P.; Ascenzi, P.; Bolognesi, M. J. Mol. Biol. 1992, 225, 107.
20. (i) Ricca, J. M.; Crout, D. H. J. Chem. Soc., Perkin Trans. 1 1989, 2126.
21. (j) Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094.
22. (k) Brieva, R.; Rebelleo, F.; Gotor, V. Chem. Commun. 1990, 1386.
23. (l) Gutman, A. L.; Meyer, E.; Kalerin, E.; Polyak, F.; Sterling, J. Biotechnol. Bioeng. 1992, 40, 760.
24. Roper, J. M.; Bauer, D. P. Synthesis 1983, 1041.
25. (a) McPhalen, C. A.; James, M. N. G. Biochemistry 1988, 27, 6582.
26. (b) Bode, W.; Papamokos, E.; Musil, D. Eur. J. Biochem. 1987, 166, 673.
27. (c) Frigerio, F.; Coda, A.; Pugliese, L.; Lionetti, C.; Menegatti, E.; Amiconi, G.; Schnebli, H. P.; Ascenzi, P.; Bolognesi, M. J. Mol. Biol. 1992, 225, 107.
28. (d) Tsukada, H.; Blow, D. M. M. J. Mol. Biol. 1985, 184, 703.
29. (e) Birktoft, J. J.; Blow, D. M. M. J. Mol. Biol. 1972, 68, 187.
30. (f) Blevins, R. A.; Tulinsky, A. J. Biol. Chem. 1985, 260, 4264.
31. (g) Tulinsky, A.; Blevins, R. A. J. Biol. Chem. 1987, 262, 7737.
32. (a) Schlechter, L; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157.
33. (b) Berger, A.; Schechter, I. Philos. Trans. R. London, Ser. B. 1970, 257, 249.
34. Lee, T.; Jones, J. B. J. Am. Chem. Soc. 1996, 118, 502.
35. (a) Lienhard, G. E. Science 1973, 180, 149.
36. (b) Wolfenden, R. V. Acc. Chem. Res. 1972, 5, 10.
37. (c) Koehler, K. A.; Lienhard, G. E. Biochemistry 1971, 10, 2477.
38. (d) Wolfenden, R. V.; Radzicka, A. Curr. Opin. Struct. Biol. 1991, 1, 780.
39. (a) Rawn, J. D.; Lienhard, G. E. Biochemistry 1974, 13, 3124.
40. (b) Tatsuta, K.; Mikami, N.; Fujimoto, K.; Umezawa, S.; Umezawa, H.; Aoyagi, T. J. Antibiot. (Tokyo). Ser. A. 1973, 26, 625.
41. (c) Ito, A.; Tokawa, K.; Shimizu, B. Biochem. Biophys. Res. Comm. 1972, 49, 343.
42. Keeffe, J. R.; Kresge, A. J. In The Chemistry of Enols; Rappoport, Z., Ed.; John Wiley & Sons: Toronto, 1990, p 399.
43. (a) Mangeney, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, J. Synthesis 1988, 255.
44. (b) Mangeney, P.; Grojean, F.; Alexakis, A.; Normant, J. F. Tetrahedron Lett.
45. (c) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1988, 29, 2677.
46. Waley, S. G. J. Biochem. 1982, 205, 631.
47. (a) Lewis, C: A., Jr.; Wolfenden, R. Biochemistry 1977, 16, 4886.
48. (b) Lewis, C. A., Jr.; Wolfenden, R. Biochemistry 1977, 16, 4895.
49. Martichonok, V.; Jones, J. B. J. Am. Chem. Soc. 1996, 118, 950.
50. (a) Tsilikounas, E.; Kettner, C. A.; Bachovchin, W. W. Biochemistry 1993, 32, 12651.
51. (b) Zhong, S.; Haghjoo, K.; Kettner, C.; Jordan, F. J. Am. Chem. Soc. 1995, 117, 7048.
52. R].
53. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: New York, 1980.
54. Evans, D. E.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
55. Stokker, G. E.; Hoffman, W. F.; Alberts, A. W.; Cragoe, E. J.; Deana, A. A.; Gilfillan, J. L.; Huff, J. W.; Novello, F. C.; Prugh, D. J.; Smith, R. L.; Willard, A. K. J. Med. Chem. 1985, 28, 347.
56. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron 1986, 42, 2675.
57. Bowers, A.; Halsall, T. G.; Jones, E. R. H.; Lemin, A. J. J. Chem. Soc. 1953, 2548.
58. 7.23 the enantiomeric excesses of the homologated chiral aldehydes R-4, S-4, R-8, and S-8 were deemed to be >95% ee. This assumption was supported by the absolute values of optical rotation of each chiral aldehyde pair R-4, S-4 and R-8, S-8 being identical, within experimental error.
59. (a) Arndt, F.; Eistert, B. Ber. 1935, 68, 200.
60. (b) Bachmann, W. E.; Struve, W. S. In Organic Reactions; Florkin, M., Stotz, E. H., Ed.; Wiley and Sons Inc.: New York, 1965; Vol. 1, pp 38-62.
61. Menicagli, R.; Piccolo, O.; Lardicci, L.; Wis, M. L. Tetrahedron 1979, 35, 1301.
62. Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559.