Chiral Amino Acid Recognition by a Porphyrin-Based Artificial Receptor

Journal of the American Chemical Society

Volumn 117, Issue 44, 1995, Pages 10950-10958

  Kuroda, Yasuhisa ^a   Kato, Yusuke ^a   Higashioji, Takuji ^a   Hasegawa, Jun Ya ^a   Kawanami, Shinichi ^a   Takahashi, Masatoshi ^a   Shiraishi, Nobuyuki ^a   Tanabe, Kazuhito ^a   Ogoshi, Hisanobu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINO ACID RECEPTOR; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC PORPHYRIN DERIVATIVE;

ARTICLE; CHIRALITY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; SPECTROPHOTOMETRY; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

EID: 0029583317     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00149a018     Document Type: Article

References (85)

1. Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009.
2. Schneider, H.J., Dürr, H., Eds.; VHC: Weinheim, 1990.
3. Vögtle, F. Supramolecular Chemistry, an Introduction; John Wiley & Sons: New York, 1991.
4. Tetrahedron 1995, 51.
5. Lehn, J.-M.; Sirlin, C. J. Chem. Soc., Chem. Commun. 1978, 949.
6. Peacock, S.C.; Domeier, L.A.; Gaeta, F.C.A.; Helgeson, R.C.; Timko, J.M.; Cram, D.J. J. Am. Chem. Soc. 1978, 100, 8190.
7. Sogah, G.D.Y.; Cram, D.J. J. Am. Chem. Soc. 1979, 101, 3035.
8. Newcomb, M.; Toner, J.L.; Helgeson, R.C.; Cram, D.J. J. Am. Chem. Soc. 1979, 101, 4971.
9. Peacock, S.S.; Walba, D.M.; Gaeta, F.C.A.; Helgeson, R.C.; Cram, D.J. J. Am. Chem. Soc. 1980, 102, 2043.
10. Davidson, R.B.; Bradshaw, J.S.; Jones, B.A.; Dailey, N.K.; Christensen, J.J.; Izatt, R.M.; Morin, F.G.; Grant, D.M. J. Org. Chem. 1984, 49, 353.
11. Naemura, K.; Fukunaga, R.; Yamanaka, M. J. Chem. Soc., Chem. Commun. 1985, 1560.
12. Murakami, Y.; Ohno, T.; Hayashida, O.; Hisaeda, Y. J. Chem. Soc., Chem. Commun. 1991, 950.
13. Behr, J.-P.; Lehn, J.-M. J. Am. Chem. Soc. 1973, 95, 6108.
14. Pirkle, W.H.; House, D.W.; Finn, J.M. J. Chromatogr. 1980, 192, 143.
15. Tsukube, H. Tetrahedron Lett. 1981, 22, 3981.
16. Echavarren, A.; Galán, A.; Lehn, J.-M.; de Mendoza, J. J. Am. Chem. Soc. 1989, 111, 4994.
17. Konishi, K.; Yahara, K.; Toshishige, H.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1994, 116, 1337.
18. Sunamoto, J.; Iwamoto, K.; Mohri, Y.; Kominato, T. J. Am. Chem. Soc. 1982, 104, 5502.
19. Rebek, J., Jr.; Askew, B.; Nemeth, D.; Parris, K. J. Am. Chem. Soc. 1987, 109, 2432.
20. Galan, A.; Andreu, D.; Echavarren, A.M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511.
21. Dobashi, A.; Hara, S. Tetrahedron Lett. 1983, 24, 1509.
22. Spisni, A.; Corradini, R.; Marchelli, R.; Dossena, A. J. Org. Chem. 1989, 54, 684.
23. Liu, R.; Sanderson, P.E.J.; Still, W.C. J. Org. Chem. 1990, 55, 5184.
24. Yoon, S.S.; Still, W.C. J. Am. Chem. Soc. 1993, 115, 823.
25. Borchardt, A.; Still, W.C. J. Am. Chem. Soc. 1994, 116, 7467.
26. Famulok, M.; Jeong, K.-S.; Deslongchamps, G.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1991, 30, 858.
27. Jeong, K.S.; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 201.
28. Cristofaro, M.F.; Chamberlin, A.R. J. Am. Chem. Soc. 1994, 116, 5089.
29. Rebek, J., Jr.; Askew, B.; Ballester, P.; Doa, M. J. Am. Chem. Soc. 1987, 109, 4119.
30. Pirkle, W.H.; Pochapsky, T.C. J. Am. Chem. Soc. 1987, 109, 5975.
31. Greenstein, J.P.; Winitz, M. Chemistry of Amino Acids; Krieger Publishing Co.: Malabar, FL, 1984.
32. Aoyama, Y.; Asakawa, M.; Yamagishi, A.; Toi, H.; Ogoshi, H. J. Am. Chem. Soc. 1990, 112, 3145.
33. Ogoshi, H.; Hatakeyama, H.; Yamamura, K.; Kuroda, Y. Chem. Lett. 1990, 51.
34. Ogoshi, H.; Hatakeyama, H.; Kotani, J.; Kawashima, A.; Kuroda, Y. J. Am. Chem. Soc. 1991, 113, 8181.
35. Kuroda, Y.; Hatakeyama, H.; Inakoshi, N.; Ogoshi, H. Tetrahedron Lett. 1993, 34, 8285.
36. Mizutani, T.; Ema, T.; Yoshida, T.; Kuroda, Y.; Ogoshi, H. Inorg. Chem. 1993, 32, 2072.
37. Kuroda, Y.; Hatakeyama, H.; Seshimo, H.; Ogoshi, H. Supramol. Chem. 1994, 3, 267.
38. Mizutani, T.; Ema, T.; Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 4240.
39. Hamilton, A.; Lehn, J.-M.; Sessler, J.L. J. Am. Chem. Soc. 1986, 108, 5158.
40. Lindsey, J.S.; Kearney, P.C.; Duff, R.J.; Tjivikua, P.T.; Rebek, J. J. Am. Chem. Soc. 1988, 110, 6575.
41. Salehi, A.; Mei, H.-Y.; Bruice, T.C. Tetrahedron Lett. 1991, 32, 3453.
42. Harriman, A.; Kubo, Y.; Sessler, J.L. J. Am. Chem. Soc. 1992, 114, 388.
43. Kuroda, Y.; Ogoshi, H. Synlett 1994, 319.
44. Smith, K.M., Ed.; Elsevier Scientific Publishing: New York, 1975.
45. Kuroda, Y.; Kato, Y.; Higashioji, T.; Ogoshi, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 723.
46. Collman, J.P.; Gagne, R.R.; Reed, C.A.; Halbert, T.R.; Lang, G.; Robinson, W.T. J. Am. Chem. Soc. 1975, 97, 1427.
47. Collman, J.P.; Brauman, J.I.; Fitzgerald, J.P.; Hampton, P.D.; Naruta, Y.; Michida, T. Bull. Chem. Soc. Jpn. 1988, 61, 47.
48. Korshak, V.V.; Rusanov, A.L.; Plieva, L.K.; Kereselidze, M.K.; Lekae, T.V. Macromolecules 1976, 9, 626.
49. Page, M.I.; Jencks, W.P. Proc. Natl. Acad. Sci. USA. 1971, 68, 1678.
50. Simanek, E.E.; Mammen, M.; Gordon, D.M.; Chin, D.; Mathias, J.P.; Seto, C.T.; Whitesides, G.M. Tetrahedron 1995, 51, 607.
51. Jeffrey, G.A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: New York, 1991.
52. Kuroda, Y.; Kato, Y.; Ito, M.; Hasegawa, J.; Ogoshi, H. J. Am. Chem. Soc. 1994, 116, 10338.
53. Wegsheider, R. Monatsh. Chem. 1916, 37, 219.
54. Wegsheider, R. J. Chem. Soc. 1916, 110, 467.
55. Venimadhavan, S.; Shelly, K.P.; Stewart, R. J. Org. Chem. 1989, 54, 2483.
56. Leffler, J.E.; Grunwald, E. Rates and Equilibria of Organic Reactions; Dover Publications, Inc.: New York, 1963.
57. Hine. J. Structural Effects on Equilibria in Organic Chemistry; John Wiley & Sons: New York. 1975.
58. Smithrud, D.B.; Wyman, T.B.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5420.
59. Stauffer, D.A.; Bassans, R.E.; Dougherty, D.A. J. Org. Chem. 1990, 55, 2762.
60. Zhu, C.Y.; Bradshaw, J.S.; Oscarson, J.L.; Izatt, R.M.J. Inclusion Phenom. 1992, 12, 275.
61. Glew, D.N.; Robertson, R.E. J. Phys. Chem. 1956, 60, 332.
62. Wassermann, A. J. Chem. Soc. 1942, 621.
63. Lumry, R.; Rajender, S. Biopolymers 1970, 9, 1125.
64. Bennetto, H.P.; Caldin, E.F. J. Chem. Soc. A 1971, 2198.
65. Ueoka, R.; Matsumoto, Y. J. Org. Chem. 1984, 49, 3774.
66. Inoue, Y.; Hakushi, T. J. Chem. Soc., Perkin Trans. 2 1985, 935.
67. Inoue, Y.; Amano, F.; Okada, N.; Inada, H.; Ouchi, M.; Tai, A.; Hakushi, T.; Liu, Y.; Tong, L.-H. J. Chem. Soc., Perkin Trans. 2 1990, 1239.
68. Inoue, Y.; Hakushi, T.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 475.
69. Macartney, D.H.; Waddling. C.A. Inorg. Chem. 1994, 33, 5912.
70. Aoyama, Y.; Asakawa, M.; Matsui, Y.; Ogoshi, H. J. Am. Chem. Soc. 1991, 113, 6233.
71. Kadish, K.M.; Schaeper, D. J. Chem. Soc., Chem. Commun. 1980, 1273.
72. Vogel, G.C.; Stahlbush, J.R. Inorg. Chem. 1977, 16, 950.
73. Cole, S.J.; Curthoys, G.C.; Magnusson, E.A.; Phillips, J.N. Inorg. Chem. 1972, 11, 1024.
74. Miller, J.R.; Gorough, G.D. J. Am. Chem. Soc. 1952, 74, 3977.
75. Walker, F.A.; Benson, M.J. J. Am. Chem. Soc. 1980, 102, 5530.
76. Cole, S.J.; Curthoys, G.C.; Magnusson, E.A. J. Am. Chem. Soc. 1970, 92, 2991.
77. Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637.
78. Wells, T.N.C.; Fersht, A.R. Biochemistry 1986, 25, 1881.
79. Ho, C.K.; Ferst, A.R. Biochemistry 1986, 25, 1891.
80. Smithrud, D.B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339.
81. Kuroda, Y.; Hiroshige, T.; Sera, T.; Shiroiwa, Y.; Tanaka, H.; Ogoshi, H. J. Am. Chem. Soc. 1989, 111, 1912.
82. Kuroda, Y.; Egawa, Y.; Seshimo, H.; Ogoshi, H. Chem. Lett. 1994, 2361.
83. Stewart, J.J.P. QCPE Bull. 1989, 9, 10.
84. Ruggli, P.; Reichwein, H. Helv. Chim. Acta 1937, 20, 905.
85. Greenstein, J.P.; Winitz, M. Chemistry of Amino Acids; Krieger Publishing Co.: Malabar, FL, 1984; pp 925—943.