A compact chemical miniature of a holoenzyme, coenzyme NADH linked dehydrogenase. Design and synthesis of bridged NADH models and their highly enantioselective reduction

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4563-4568

  Kanomata, Nobuhiro ^a,b   Nakata, Tadashi ^c  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b MEIJI UNIVERSITY   (Japan)

^c INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; KETONE DERIVATIVE; LACTATE DEHYDROGENASE; MAGNESIUM ION; NICOTINIC ACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CHIRALITY; ENANTIOMER; PROTON TRANSPORT; REDUCTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034679096     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992990y     Document Type: Article

References (64)

1. A part of this work has previously been published as a communication: Kanomata, N.; Nakata, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1207-1211.
2. (a) Loewus, F. A.; Ofner, P.; Fisher, H. F.; Westheimer, F. H.; Vennesland, B. J. Biol. Chem. 1953, 202, 699-704.
3. (b) You, K.-s. CRC Crit. Rev. Biochem. 1984, 17, 313-451.
4. (a) Holbrook, J. J.; Liljas, A.; Steindel, S. J.; Rossmann, M. G. In The Enzymes, 3rd ed.; Boyer, P. D., Ed.; Academic Press: New York, 1975; Vol. XI, pp 191-292.
5. (b) Brändén, C.-I.; Eklund, H. In Dehydrogenases Requiring Nicotinamide Coenzymes; Jeffery, J., Ed.; Birkhauser Verlag: Basel, 1980; pp 40-84.
6. Recent review articles: (a) Kanomata, N. J. Synth. Org. Chem., Jpn. 1999, 57, 512-522. (b) Murakami, Y.; Kikuchi, J.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (c) Dupas, G.; Levacher, V.; Bourguignon, J.; Quéguiner, G. Heterocycles 1994, 39, 405-429. (d) Burgess, V. A.; Davies, S. G.; Skerlj, R. T. Tetrahedron: Asymmetry 1991, 2, 299- 328.
7. Recent review articles: (a) Kanomata, N. J. Synth. Org. Chem., Jpn. 1999, 57, 512-522. (b) Murakami, Y.; Kikuchi, J.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (c) Dupas, G.; Levacher, V.; Bourguignon, J.; Quéguiner, G. Heterocycles 1994, 39, 405-429. (d) Burgess, V. A.; Davies, S. G.; Skerlj, R. T. Tetrahedron: Asymmetry 1991, 2, 299- 328.
8. Recent review articles: (a) Kanomata, N. J. Synth. Org. Chem., Jpn. 1999, 57, 512-522. (b) Murakami, Y.; Kikuchi, J.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (c) Dupas, G.; Levacher, V.; Bourguignon, J.; Quéguiner, G. Heterocycles 1994, 39, 405-429. (d) Burgess, V. A.; Davies, S. G.; Skerlj, R. T. Tetrahedron: Asymmetry 1991, 2, 299- 328.
9. Recent review articles: (a) Kanomata, N. J. Synth. Org. Chem., Jpn. 1999, 57, 512-522. (b) Murakami, Y.; Kikuchi, J.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721-758. (c) Dupas, G.; Levacher, V.; Bourguignon, J.; Quéguiner, G. Heterocycles 1994, 39, 405-429. (d) Burgess, V. A.; Davies, S. G.; Skerlj, R. T. Tetrahedron: Asymmetry 1991, 2, 299-328.
10. (a) Ohno, A.; Ikeuchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036-7040.
11. (b) Mikata, Y.; Hayashi, K.; Mizukami, K.; Matsumoto, S.; Yano, S.; Yamazaki, N.; Ohno, A. Tetrahedron Lett. 2000, 41, 1035-1038. Ohno, A.; Kashiwagi, M.; Ishihara, Y. Tetrahedron 1986, 42, 961-973.
12. (b) Mikata, Y.; Hayashi, K.; Mizukami, K.; Matsumoto, S.; Yano, S.; Yamazaki, N.; Ohno, A. Tetrahedron Lett. 2000, 41, 1035-1038. Ohno, A.; Kashiwagi, M.; Ishihara, Y. Tetrahedron 1986, 42, 961-973.
13. (c) de Kok, P. M. T.; Bastiaansen, L. A. M.; van Lier, P. M.; Vekemans, J. A. J. M.; Buck, H. M. J. Org. Chem. 1989, 54, 1313-1320.
14. (d) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1996. Meyers, A. I.; Brown, J. D. J. Am. Chem. Soc. 1987, 109, 3155- 3156.
15. (d) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989- 1996. Meyers, A. I.; Brown, J. D. J. Am. Chem. Soc. 1987, 109, 3155-3156.
16. (a) Combret, Y.; Torché, J. J.; Plé, N.; Duflos, J.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron 1991, 47, 9369-9382.
17. (b) Combret, Y.; Torché, J. J.; Binay, P.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Chem. Lett. 1991, 125-128.
18. (c) Combret, Y.; Duflos, J.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron 1993, 49, 5237-5246.
19. (d) Bédat, J.; Levacher, V.; Dupas, G.; Quéguiner, G.; Bourguignon, J. Chem. Lett. 1995, 327-328. Bédat, J.; Levacher, V.; Dupas, G.; Quéguiner, G.; Bourguignon, J. Chem. Lett. 1996, 359-360.
20. (d) Bédat, J.; Levacher, V.; Dupas, G.; Quéguiner, G.; Bourguignon, J. Chem. Lett. 1995, 327-328. Bédat, J.; Levacher, V.; Dupas, G.; Quéguiner, G.; Bourguignon, J. Chem. Lett. 1996, 359-360.
21. (e) Leroy, C.; Levacher, V.; Dupas, G.; Quéguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1997, 8, 3309-3318.
22. Burgess, V. A.; Davies, S. G.; Skerlj, R. T.; Whittaker, M. Tetrahedron: Asymmetry 1992, 3, 871-901, Burgess, V. A.; Davies, S. G.; Skerlj, R. T. J. Chem. Soc., Chem. Commun. 1990, 1759-1762. Davies, S. G.; Skerlj, R. T.; Whittaker, M. Tetrahedron: Asymmetry 1990, 1, 725- 728.
23. Burgess, V. A.; Davies, S. G.; Skerlj, R. T.; Whittaker, M. Tetrahedron: Asymmetry 1992, 3, 871-901, Burgess, V. A.; Davies, S. G.; Skerlj, R. T. J. Chem. Soc., Chem. Commun. 1990, 1759-1762. Davies, S. G.; Skerlj, R. T.; Whittaker, M. Tetrahedron: Asymmetry 1990, 1, 725- 728.
24. Burgess, V. A.; Davies, S. G.; Skerlj, R. T.; Whittaker, M. Tetrahedron: Asymmetry 1992, 3, 871-901, Burgess, V. A.; Davies, S. G.; Skerlj, R. T. J. Chem. Soc., Chem. Commun. 1990, 1759-1762. Davies, S. G.; Skerlj, R. T.; Whittaker, M. Tetrahedron: Asymmetry 1990, 1, 725-728.
25. (a) Seki, M.; Baba, N.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1981, 103, 4613-4615.
26. (b) Hoshide, F.; Ohi, S.; Baba, N.; Oda, J.; Inouye, Y. Agric. Biol. Chem. 1982, 46, 2173-2175.
27. (c) Seki, M.; Baba, N.; Oda, J.; Inouye, Y. J. Org. Chem. 1983, 48, 1370-1373.
28. (d) Skog, K.; Wennerström, O. Tetrahedron Lett. 1992, 33, 1751-1754.
29. de Vries, J. G.; Kellogg, R. M. J. Am. Chem. Soc. 1979, 101, 2759-2761. Jouin, P.; Troostwijk, C. B.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 2091-2093. Talma, A. G.; Jouin, P.; de Vries, J. G.; Troostwijk, C. B.; Werumeus Buning, G. H.; Waninge, J. K.; Visscher, J.; Kellogg, R. M. J. Am. Chem. Soc. 1985, 107, 3981-3997.
30. de Vries, J. G.; Kellogg, R. M. J. Am. Chem. Soc. 1979, 101, 2759- 2761. Jouin, P.; Troostwijk, C. B.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 2091-2093. Talma, A. G.; Jouin, P.; de Vries, J. G.; Troostwijk, C. B.; Werumeus Buning, G. H.; Waninge, J. K.; Visscher, J.; Kellogg, R. M. J. Am. Chem. Soc. 1985, 107, 3981-3997.
31. de Vries, J. G.; Kellogg, R. M. J. Am. Chem. Soc. 1979, 101, 2759- 2761. Jouin, P.; Troostwijk, C. B.; Kellogg, R. M. J. Am. Chem. Soc. 1981, 103, 2091-2093. Talma, A. G.; Jouin, P.; de Vries, J. G.; Troostwijk, C. B.; Werumeus Buning, G. H.; Waninge, J. K.; Visscher, J.; Kellogg, R. M. J. Am. Chem. Soc. 1985, 107, 3981-3997.
32. Chiral sulfoxide models: (a) Imanishi, T.; Hamano, Y.; Yoshikawa, H.; Iwata, C. J. Chem. Soc., Chem. Commun. 1988, 473-475. (b) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Iwata, C.; Imanishi, T. Tetrahedron 1997, 53, 593-602. (c) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Chem. Lett. 1996, 853-854. Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Tetrahedron 1997, 53, 3073-3082. (d) Obika, S.; Nishiyama, T.; Tatematsu, S.; Nishimoto, M.; Miyashita, K.; Imanishi, T. Heterocycles 1998, 49, 261-267.
33. Chiral sulfoxide models: (a) Imanishi, T.; Hamano, Y.; Yoshikawa, H.; Iwata, C. J. Chem. Soc., Chem. Commun. 1988, 473-475. (b) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Iwata, C.; Imanishi, T. Tetrahedron 1997, 53, 593-602. (c) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Chem. Lett. 1996, 853-854. Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Tetrahedron 1997, 53, 3073-3082. (d) Obika, S.; Nishiyama, T.; Tatematsu, S.; Nishimoto, M.; Miyashita, K.; Imanishi, T. Heterocycles 1998, 49, 261-267.
34. Chiral sulfoxide models: (a) Imanishi, T.; Hamano, Y.; Yoshikawa, H.; Iwata, C. J. Chem. Soc., Chem. Commun. 1988, 473-475. (b) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Iwata, C.; Imanishi, T. Tetrahedron 1997, 53, 593-602. (c) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Chem. Lett. 1996, 853-854. Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Tetrahedron 1997, 53, 3073-3082. (d) Obika, S.; Nishiyama, T.; Tatematsu, S.; Nishimoto, M.; Miyashita, K.; Imanishi, T. Heterocycles 1998, 49, 261-267.
35. Chiral sulfoxide models: (a) Imanishi, T.; Hamano, Y.; Yoshikawa, H.; Iwata, C. J. Chem. Soc., Chem. Commun. 1988, 473-475. (b) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Iwata, C.; Imanishi, T. Tetrahedron 1997, 53, 593-602. (c) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Chem. Lett. 1996, 853-854. Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Tetrahedron 1997, 53, 3073-3082. (d) Obika, S.; Nishiyama, T.; Tatematsu, S.; Nishimoto, M.; Miyashita, K.; Imanishi, T. Heterocycles 1998, 49, 261-267.
36. Chiral sulfoxide models: (a) Imanishi, T.; Hamano, Y.; Yoshikawa, H.; Iwata, C. J. Chem. Soc., Chem. Commun. 1988, 473-475. (b) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Iwata, C.; Imanishi, T. Tetrahedron 1997, 53, 593-602. (c) Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Chem. Lett. 1996, 853-854. Obika, S.; Nishiyama, T.; Tatematsu, S.; Miyashita, K.; Imanishi, T. Tetrahedron 1997, 53, 3073-3082. (d) Obika, S.; Nishiyama, T.; Tatematsu, S.; Nishimoto, M.; Miyashita, K.; Imanishi, T. Heterocycles 1998, 49, 261-267.
37. (a) Vasse, J. L.; Charpentier, P.; Levacher, V.; Dupas, G.; Quéguiner, G.; Bourguignon, J. Synlett 1998, 1144-1146.
38. (b) Versleijen, J. P.; Sanders-Hovens, M. S.; Vanhommerig, S. A.; Vekemans, J. A.; Meijer, E. M. Tetrahedron 1993, 49, 7793-7802.
39. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
40. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
41. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
42. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
43. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
44. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
45. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
46. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
47. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
48. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
49. 6 models: (g) Koh, J. T.; Delaude, L.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 11234-11240. (h) Kuzuhara, H.; Iwata, M.; Emoto, S. J. Am. Chem. Soc. 1977, 99, 4173-4175. (i) Tachibana, Y.; Ando, M.; Kuzuhara, H. Bull. Chem. Soc. Jpn. 1983, 56, 3652-3656. Tachibana, Y.; Ando, M.; Kuzuhara, H. Chem. Lett. 1982, 1765-1768.
50. Kanomata, N.; Nakata, T. Heterocycles 1998, 48, 2551-2558.
51. (a) Kanomata, N.; Nitta, M. Tetrahedron Lett. 1988, 29, 5957-5960. Kanomata, N.; Nitta, M. J. Chem. Soc., Perkin Trans. 1 1990, 1119- 1126.
52. (a) Kanomata, N.; Nitta, M. Tetrahedron Lett. 1988, 29, 5957- 5960. Kanomata, N.; Nitta, M. J. Chem. Soc., Perkin Trans. 1 1990, 1119-1126.
53. (c) Nitta, M.; Akie, T.; Iino, Y. J. Org. Chem. 1994, 59, 1309-1314.
54. (a) Marson, C. M.; Giles, P. R. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, 1994.
55. (b) Virgilio, J. A.; Heiweil, E. Org. Prep. Proced. Int. 1982, 14, 9-20.
56. (c) Ziegenbein, W.; Lang, W. Chem. Ber. 1960, 93, 2743-2749.
57. 3) δ 1.79 (m, 2H), 2.24 (t, J = 7.5 Hz, 2H), 2.62 (t, J = 7.7 Hz, 2H), 10.1 (s, 1H); the other signals (14H) were overlapped with those of trans-2. Warming the mixture of cis- and trans-2 caused the rapid transformation of cis-2 into azirine 3 even at room temperature.
58. 3 is δ 10.72 ppm: Tabyaoui, B.; Aubert, T.; Farnier, M.; Guilard, R. Synth. Commun. 1988, 18, 1475-1482.
59. Our previous communication discusses the reaction pathways for the formation of 5 and 6. See ref 1. For further synthetic application of formyl-substituted (vinylimino)phosphoranes to highly functional pyridines, see ref 13.
60. Jacobi, P. A.; Zheng, W. Tetrahedron Lett. 1993, 34, 2585-2588.
61. The dihydropyridines 10a-c were used in the next step immediately without further purification. These compounds are apparently sensitive to oxygen.
62. Geminal C-4 protons of 10c (δ 2.80 and δ 2.89) were unequivocally assigned by the COSY, HMQC, HMBC, and NOE differencial spectra. The NOE enhancement (3%) was observed between the inner proton (δ 2.89) and one of the oligomethylene protons (δ 1.60).
63. Toyooka, Y.; Matsuzawa, T.; Eguchi, T.; Kakinuma, K. Tetrahedron 1995, 51, 6459-6474.
64. Kanomata, N.; Suzuki, M.; Yoshida, M.; Nakata, T. Angew. Chem., Int. Ed. 1998, 37, 1410-1412.