Atropisomeric transition state analogs

European Journal of Organic Chemistry

Volumn , Issue 7, 2000, Pages 1365-1372

  Ritzeler, Olaf ^a,c   Parel, Serge ^a   Therrien, Bruno ^a   Bensel, Nicolas ^a   Reymond, Jean Louis ^a   Schenk, Kurt ^b  

^a UNIVERSITY OF BERN   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

^c SANOFI   (France)

Author keywords

Atropisomerism; Enzyme inhibitors; Transition states

Indexed keywords

1 NAPHTHOL; ACETONE; DIHYDROQUINOLINE DERIVATIVE; ENZYME INHIBITOR;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; MOLECULAR DYNAMICS; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SIMULATION; STEREOISOMERISM;

EID: 0034051952     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200004)2000:7<1365::AID-EJOC1365>3.0.CO;2-X     Document Type: Article

References (78)

1. J. Kraut, Science 1988, 242, 533 and refs. cited therein.
2. [2a] J. L. Kurz, Acc. Chem. Res. 1972, 5, 1-9.
3. [2b] O. S. Tee, Adv. Phys. Org. Chem. 1994, 29, 1-85.
4. [2c] R. Wolfenden, Acc. Chem. Res. 1972, 5, 10-18.
5. [2d] G. E. Lienhard, Science 1973, 180, 149-154.
6. [2e] J.-L. Reymond, Y. Chen, Isr. J. Chem. 1996, 36, 199-206.
7. [3a] M. M. Mader, P. A. Bartlett, Chem. Rev. 1997, 97, 1281-1301.
8. [3b] J. D. Stewart, S. J. Benkovic, Nature 1995, 375, 388-391.
9. [3c] A. J. Kirby, Angew. Chem. 1996, 108, 771-790; Angew. Chem. Int. Ed. Engl. 1996, 35, 707-724.
10. [3c] A. J. Kirby, Angew. Chem. 1996, 108, 771-790; Angew. Chem. Int. Ed. Engl. 1996, 35, 707-724.
11. [3d] I. Fujii, F. Tanaka, H. Miyashita, R. Tanimura, K. Kinoshita, J. Am. Chem. Soc. 1995, 117, 6199-6209.
12. [4a] P. G. Schultz, R. A. Lerner, Science 1995, 269, 1835-1842.
13. [4b] J.-L. Reymond, Top. Curr. Chem. 1999, 200, 59-93.
14. H. Primas, U. Müller-Herold in Elementare Quantenchemie, 2. Aufl./2nd Ed., Teubner, Stuttgart, 1990, p. 189-190.
15. Compound types other than transition state analogs can be utilized to prepare enzyme inhibitors and/or haptens inducing catalytic antibodies. Examples include suicide inhibitors, bait and switch, and reactive immunizations.
16. M. Bols, Acc. Chem. Res. 1998, 31, 1-8 and refs. cited therein.
17. [8a] L. J. Liotta, R. A. Gibbs, S. D. Taylor, P. A. Benkovic, S. J. Benkovic, J. Am. Chem. Soc. 1995, 117, 4729-4741.
18. [8b] O. Ersoy, R. Fleck, A. Sinskey, S. Masamune, J. Am. Chem. Soc. 1996, 118, 13077-13078.
19. [9a] K. D. Janda, C. G. Shevlin, R. A. Lerner, Science 1993, 259, 490-493.
20. [9b] K. D. Janda, C. G. Shevlin, R. A. Lerner, J. Am. Chem. Soc. 1995, 117, 2659-2560.
21. [10a] T. Li, K. D. Janda, J. A. Ashley, R. A. Lerner, Science 1994, 264, 1289-1293.
22. [10b] T. Li, S. Hilton, K. D. Janda, J. Am. Chem. Soc. 1995, 117, 3308-3309.
23. [10c] T. Li, K. D. Janda, R. A. Lerner, Nature 1996, 379, 326-327.
24. [10d] J. Hasserodt, K. D. Janda, R. A. Lerner, J. Am. Chem. Soc. 1996, 118, 11654-11655 and 1997, 119, 5993-5998.
25. [10d] J. Hasserodt, K. D. Janda, R. A. Lerner, J. Am. Chem. Soc. 1996, 118, 11654-11655 and 1997, 119, 5993-5998.
26. [10e] J. Hasserodt, K. D. Janda, Tetrahedron 1997, 53, 11237-11255.
27. A. C. Braisted, P. G. Schultz, J. Am. Chem. Soc. 1994, 116, 2211-2212.
28. Z. S. Zhou, N. Jiang, D. Hilvert, J. Am. Chem. Soc. 1997, 119, 3623-3624.
29. S. S. Yoon, Y. Oei, E. Sweet, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 11686-11687.
30. D. Y. Jackson, P. G. Schultz, J. Am. Chem. Soc. 1991, 113, 2319-2320.
31. T. Uno, J. Ku, J. R. Prudent, A. Huang, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 3811-3817.
32. [16a] P. A. Bartlett, C. R. Johnson, J. Am. Chem. Soc. 1985, 107, 7792-7793.
33. [16b] D. Y. Jackson, J. W. Jacobs, R. Sugasawara, S. H. Reich, P. A. Bartlett, P. G. Schultz, J. Am. Chem. Soc. 1988, 110, 4841-4842.
34. [16c] M. R. Haynes, F. A. Stura, D. Hilvert, I. A. Wilson, Science 1994, 263, 646-652.
35. [17a] D. Hilvert, K. W. Hill, K. D. Nared, M.-R. M. Auditor, J. Am. Chem. Soc. 1989, 111, 9261-9262.
36. [17b] A. C. Braisted, P. G. Schultz, J. Am. Chem. Soc. 1990, 112, 7430-7431.
37. [17c] V. E. Gouverneur, K. N. Houk, B. de Pascual-Teresa, B. Beno, K. D. Janda, R. A. Lerner, Science 1993, 262, 204-208.
38. [17d] C. J. Suckling, M. C. Tedford, L. M. Bence, J. I. Irvine, W. H. Stimson, J. Chem. Soc., Perkin Trans. 1 1993, 1925-1929.
39. [17e] A. A. P. Meekel, M. Resmini, U. K. Pandit, Bioorg. Med. Chem. 1996, 4, 1051-1057.
40. B. F. Cravatt, J. A. Ashley, K. D. Janda, D. L. Boger, R. A. Lerner, J. Am. Chem. Soc. 1994, 116, 6013-6014.
41. H. Suga, N. Tanimoto, A. J. Sinskey, S. Masamune, J. Am. Chem. Soc. 1994, 116, 11197-11198.
42. J. T. Yli-Kauhaluoma, J. A. Ashley, C.-H. Lo, J. Coakley, P. Wirsching, K. D. Janda, J. Am. Chem. Soc. 1996, 118, 5496-5497.
43. M. Oki, Top. Stereochem. 1983, 14, 1-79.
44. [22a] J. Clayden, Angew. Chem. 1997, 109, 985-987; Angew. Chem. Int. Ed. Engl. 1997, 36, 949-951.
45. [22a] J. Clayden, Angew. Chem. 1997, 109, 985-987; Angew. Chem. Int. Ed. Engl. 1997, 36, 949-951.
46. [22b] J. Clayden, M. Darbyshire, J. H. Pink, N. Westlund, F. X. Wilson, Tetrahedron Lett. 1997, 38, 8587-8590.
47. [23a] M. G. Rossman, A. Liljas, C.-I. Brändén, L. J. Banaszak, "Evolutionary and structural relationship among dehydrogenases", in The Enzymes, Academic Press, Inc., 1975, vol. 11, p. 61.
48. [23b] N. J. Oppenheimer, A. L. Handlon, "Mechanism of NAD-dependent enzymes", in The Enzymes, Academic Press, Inc., 1992, vol. 20, p. 453.
49. J. Schröer, M. Sanner, J-L. Reymond, R. A. Lerner. J. Org. Chem. 1997, 62, 3220-3229.
50. A. D. Mesecar, B. L. Stoddard, D. E. Koshland, Jr., Science 1997, 277, 202-206.
51. [26a] J. W. Verhoeven, W. van Gerresheim, F. M. Martens, S. M. van der Kerk, Tetrahedron 1986, 42, 975-992.
52. [26b] Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 1987, 109, 2226-2227.
53. [26c] O. Tapia, R. Cardenas, F. Colonna-Cesari, J. Am. Chem. Soc. 1988, 110, 4046-4047.
54. [26d] J. Wilkie, I. H. Williams, J. Am. Chem. Soc. 1992, 114, 5423-5425.
55. [26e] Y.-D. Wu, D. K. W. Lai, K. N. Houk, J. Am. Chem. Soc. 1995, 117, 4100-4108.
56. [27a] Ö. Almarsson, R. Karaman, T. C. Bruice, J. Am. Chem. Soc. 1992, 114, 8702-8703.
57. [27b] Ö. Almarsson, T. C. Bruice, J. Am. Chem. Soc. 1993, 115, 2125-2138.
58. [27c] B. Schiøtt, Y.-J. Zheng, T. C. Bruice, J. Am. Chem. Soc. 1998, 120, 7192-7200.
59. L. C. Hsieh, S. Yonkovich, L. Kochersperger, P. G. Schultz, Science 1993, 260, 337-339.
60. H.-J. Hofmann, R. Cimiraglia, FEBS Lett. 1988, 241, 38-40 and refs. cited therein.
61. K. P. Nambiar, D. M. Stauffer, P. A. Kolodziej, S. A. Benner, J. Am. Chem. Soc. 1983, 105, 5886-5890.
62. [31a] A. Ohno, Y. Ishikawa, N. Yamazaki, M. Okamura, Y. Kawai, J. Am. Chem. Soc. 1998, 120, 1186-1192.
63. [31b] A. Ohno, Y. Ishihara, S. Ushida, S. Oka, Tetrahedron Lett. 1982, 31, 3185-3188.
64. [31c] S. Shinkai, H. Hamada, O. Manabe, Tetrahedron Lett. 1979, 1397-1400.
65. [32a] S. M. Abdel-Wahhab, L. S. El-Assad, J. Ind. Chem. Soc. 1969, 46, 927-932.
66. [32b] O. Muraoka, G. Tanabe, K. Sano, T. Minematsu, J. Chem. Soc., Perkin Trans, 1 1994, 1833-1845.
67. P. M. T. de Kok, L. A. M. Bastiaansen, P. M. van Lier, J. A. J. M. Vekemans, H. M. Buck, J. Org. Chem. 1989, 54, 1313-1320.
68. Recent examples of stereoselective hydride transfer with pyridine cofactors:[34a] N. Kanomata, M. Suzuki, M. Yoshida, T. Nakata, Angew. Chem. 1998, 110, 1506-1508; Angew. Chem. Int Ed. Engl. 1998, 37, 1410-1412.
69. Recent examples of stereoselective hydride transfer with pyridine cofactors:[34a] N. Kanomata, M. Suzuki, M. Yoshida, T. Nakata, Angew. Chem. 1998, 110, 1506-1508; Angew. Chem. Int Ed. Engl. 1998, 37, 1410-1412.
70. [34b] N. Kanomata, T. Nakata, Angew. Chem. 1997, 109, 1263-1266; Angew. Chem. Int. Ed. Engl. 1997, 36, 1207-1211.
71. [34b] N. Kanomata, T. Nakata, Angew. Chem. 1997, 109, 1263-1266; Angew. Chem. Int. Ed. Engl. 1997, 36, 1207-1211.
72. [34c] S. Obika, T. Nishiyama, S. Tatematsu, K. Miyashita, C. Iwata, T. Imanishi, Tetrahedron 1997, 53, 593-602.
73. [34d] T. Eguchi, M. Fukuda, Y. Toyooka, K. Kakinuma, Tetrahedron 1998, 54, 705-714.
74. A. Ohno, M. Ohara, S. Oka, J. Am. Chem. Soc. 1986, 108, 6438-6440.
75. Related study on naphthylcarbinols: D. Casarini, L. Lunazzi, A. Mazzanti, J. Org. Chem. 1997, 62, 3315-3323.
76. H. Günther, NMR-Spektroskopie, 3rd ed., Georg Thieme Verlag, Stuttgart, 1992, pp. 304-322.
77. J.-L. Reymond, Angew. Chem. 1995, 107, 2471-2473; Angew. Chem. Int. Ed. Engl. 1995, 34, 2285-2287.
78. J.-L. Reymond, Angew. Chem. 1995, 107, 2471-2473; Angew. Chem. Int. Ed. Engl. 1995, 34, 2285-2287.