Stepwise Approach toward First Generation Nonenzymatic Hydrolases

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2548-2559

  Madder, Annemieke ^a   De Clercq, Pierre J ^a   Declercq, Jean Paul ^b  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342917438     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971935+     Document Type: Article

References (46)

1. Murakami, Y.; Kikuchi, J.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721.
2. Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 707.
3. "... but amide cleavage is one of the most daunting challenges for manmade catalysts, and so far we are not even close.": see ref 2, p 709.
4. (a) Bender, M. L.; D'Souza, V. T. Acc. Chem. Res. 1987, 20, 146.
5. (b) Breslow, R. Acc. Chem. Res. 1995, 28, 146.
6. Lehn, J. M.; Sirlin, C. J. Chem. Soc., Chem. Commun. 1978, 949.
7. (a) Cram, D. J.; Lam, P. Y.; Ho, P. S. J. Am. Chem. Soc. 1986, 108, 839.
8. (b) Tecilla, P.; Jubian, V.; Hamilton, A. D. Tetrahedron 1995, 51, 435.
9. For a recent and noteworthy exception involving the esteriflcation of 4-(hydroxymethyl)pyridine by acetylimidazole both being bound inside the cavity of a cyclic porphyrin trimer, see: Mackay, L. G.; Wylie, R. S.; Sanders, J. K. M. J. Am. Chem. Soc. 1994, 116, 3141.
10. Atassi, M. Z.; Manshouri, T. Proc. Natl. Acad. Sci. U.S.A. 1994, 90, 8282.
11. (a) Matthews, B. W.; Craik, C. S.; Neurath, H. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4103.
12. (b) Corey, D. R.; Phillips, M. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4106.
13. (c) Wells, J. A.; Fairbrother, W. J.; Otlewski, J.; Laskowski Jr., M.; Burnier, J. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4110.
14. Hahn, K. W.; Klis, W. A.; Stewart, J. M. Science 1990, 248, 1544.
15. Blow, D. M. Acc. Chem. Res. 1976, 9, 145.
16. Zimmerman, S. C.; Korthals, J. S.; Cramer, K. D. Tetrahedron 1991, 47, 2649.
17. Warshel, A.; Russell, S. J. Am. Chem. Soc. 1986, 108, 6569.
18. Neurath, H. Science 1984, 224, 350.
19. Hogan, J. C.; Gandour, R. D. J. Org. Chem. 1991, 56, 2821.
20. (a) Anoardi, L.; Tonellato, U. J. Chem. Soc., Chem. Commun. 1977, 401.
21. (b) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866.
22. (c) Khan, M. N. J. Org. Chem. 1985, 50, 4851.
23. However, examples of GBC-hydrolysis of PNPA were reported, see: (a) Hine, J.; Khan, M. N. J. Am. Chem. Soc. 1977, 99, 3847. (b) Werber, M. M.; Shalitin, Y. Bioorg. Chem. 1973, 2, 202.
24. However, examples of GBC-hydrolysis of PNPA were reported, see: (a) Hine, J.; Khan, M. N. J. Am. Chem. Soc. 1977, 99, 3847. (b) Werber, M. M.; Shalitin, Y. Bioorg. Chem. 1973, 2, 202.
25. (a) Flaugh, M. E.; Crowell, T. A.; Farlow, D. S. J. Org. Chem. 1980, 45, 5399.
26. (b) Meyer, W. L.; Brannon, M. J.; da Burgos, C. G.; Goodwin, T. E.; Howard, R. W. J. Org. Chem. 1985, 50, 438.
27. Evans, D. A.; Nelson, J. V. J. Am. Chem. Soc. 1980, 102, 774.
28. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
29. Originally the TBDMS protective group was also chosen for the all-cis series. Problems encountered during later deprotection steps led us eventually to use the TES ether as protective group.
30. Mattson, R. J.; Pham, K. M.; Leuck, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552.
31. The synthesis of the corresponding enantiomer has been described before: Steels, I.; De Clercq, P. J.; Declercq, J. P. Tetrahedron: Asymmetry 1992, 3, 599.
32. Figure 2b shows the global energy minimum among several minimal energy conformations that were found. The geometry was calculated using MacroModel V3.0: Still, W. C.; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Lipton, M.; Liskamp, R.; Chang, G.; Hendrickson, T.; DeGunst, F.; Hasel, W.; Department of Chemistry, Columbia University, New York, 10027.
33. 1H NMR resonance at δ= 4.68 ppm was found to integrate for the expected 1H.
34. 1H NMR over a period of at least one half-life. Since the reactions were monitored by following the relative integrations of AcIm, a compound present in a very low concentration (cf. pseudo first-order conditions), monitoring over more extended time periods was inappropriate. However, in cases when half-lives were determined over at least five lifetimes using more sensitive UV methodology, values of the same order of magnitude are obtained (see ref 29b): 649,144, and 108 min for 1, 2, and 3, respectively. These values are consistently lower than those mentioned in Table 1, which is in line with the somewhat higher temperature at which the UV experiments were run (25°C).
35. Steels, I.; De Clercq, P. J.; Maskill, H. J. Chem. Soc., Chem. Commun. 1993, 294,
36. (a) Oakenfull, D. G.; Jencks, W. P. J. Am. Chem. Soc. 1971, 93, 178.
37. (b) Oakenfull, D. G.; Salvesen, K.; Jencks, W. P. J. Am. Chem. Soc. 1971, 93, 188.
38. (c) Fife, T. H. Acc. Chem. Res. 1993, 26, 325.
39. (a) Madder, A.; De Clercq, P. J.; Maskill, H. J. Chem. Soc., Perkin Trans. 2 1997, 851.
40. (b) Madder, A.; Sebastian, S.; Van Haver, D.; De Clercq, P. J.; Maskill, H. J. Chem. Soc., Perkin Trans. 2 1997, 2787.
41. Note that for reasons of clarity the enantiomer of 6t is represented in the scheme.
42. Komiyama, M.; Bender, M. L. J. Am. Chem. Soc. 1978, 100, 5977.
43. It should be stressed that under the pseudo first-order conditions (10-fold excess of amino alcohol) minute amounts of water are sufficient for complete hydrolysis.
44. Caplow, M. J. Am. Chem. Soc. 1969, 91, 3639.
45. We acknowledge this particular suggestion by one of the referees.
46. Henderson, J. W.; Haake, P. J. Org. Chem. 1977, 42, 3989.