Rational catalyst design via imprinted nanostructured materials

Chemistry of Materials

Volumn 8, Issue 8, 1996, Pages 1820-1839

  Davis, Mark E ^a   Katz, Alexander ^a   Ahmad, Wayez R ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037904257     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm960019u     Document Type: Review

References (141)

1. Wulff, G. ACS Symp. Ser. 1986, 308, 186.
2. Shea, K. J. Trends Polym. Sci. 1994, 2, 166.
3. (a) Mosbach, K. Trends Biochem. Sci. 1994, 19, 9.
4. (b) Mosbach, K; Ramström, O. Bio/Technology 1996, 14, 163.
5. Kempe, M.; Mosbach, K. J. Chromatogr. 1995, 694, 3.
6. Vidyasankar, S.; Arnold, F. H. Curr. Op. Biotech. 1995, 6, 218.
7. Chem. Eng. News 1949, 27(13), 913.
8. Pauling, L. J. Am. Chem. Soc. 1940, 62, 2643.
9. Dickey, F. H. Proc. Natl. Acad. Sci. U.S.A. 1949, 35, 227.
10. Dickey, F. H. J. Phys. Chem. 1955, 59, 695.
11. Haldeman, R. G.; Emmett, P. H. J. Phys. Chem. 1955, 59, 1039.
12. Curti, R.; Colombo, U. J. Am. Chem. Soc. 1952, 74, 3961.
13. Wulff, G.; Sarhan, A. Angew. Chem., Int. Ed. Engl. 1972, 11, 341.
14. Fischer, E. Ber. Dtsch. Chem. Ges. 1890, 23, 2611.
15. Koshland, D. E. Jr. Proc. Natl. Acad. Sci. U.S.A. 1958, 44, 98.
16. Koshland, D. E. Jr. Angew Chem., Int. Ed. Engl. 1994, 33, 2375.
17. (a) Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W. H. Freeman: New York, 1985.
18. (b) Creighton, T. E. Proteins: Structure and Molecular Properties, 2nd ed.; W. H. Freeman: New York, 1993.
19. Gerstein, M.; Lesk, A. M.; Chothia, C. Biochemistry 1994, 33, 6739.
20. Affleck, R.; Xu, Z. F.; Suzawa, V.; Focht, K.; Clark, D. S.; Dordick, J. S. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 1100.
21. Pauling, L. Chem. Eng. News 1946, 24, 1375.
22. Radzicka, A.; Wolfenden, R. Science 1995, 267, 90.
23. (a) Boudart, M. Chem. Rev. 1995, 95, 661.
24. (b) Weisz, P. CHEMTECH 1982, 22, 424.
25. Pauling, L. Am. Sci. 1948, 36, 51.
26. Tramontano, A.; Janda, K. O.; Lerner, R. A. Science 1986, 234, 1566.
27. Pollack, S. J.; Jacobs, J. W.; Schultz, P. G. Science 1986, 234, 1570.
28. Schultz, P. G.; Lerner, R. A. Acc. Chem. Res. 1993, 26, 391.
29. Schultz, P. Acc. Chem. Res. 1989, 22, 287.
30. Schultz, P.; Lerner, R. A.; Benkovic, S. J. Chem. Eng. News 1990, 68(22), 26.
31. Stewart, J. D.; Liotta, L. J.; Benkovic, S. J. Acc. Chem. Res. 1993, 26, 396.
32. Schultz, P. G.; Lerner, R. A. Science 1995, 269, 1835.
33. Haynes, M. R.; Stura, E. A.; Hilvert, D.; Wilson, I. A. Science 1994, 263, 646.
34. Hilvert, D.; Carpenter, S. H.; Nared, K. D.; Auditor, M. T. M. Proc. Natl. Acad. Sci. U.S.A. 1989, 85, 4953.
35. Hilvert, D.; Nared, K. D. J. Am. Chem. Soc. 1988, 110, 5593.
36. Jackson, D. Y.; Liang, M. N.; Bartlett, P. A.; Schultz, P. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 182.
37. Chook, Y. M.; Ke, H.; Lipscomb, W. N. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8600.
38. Thorn, S. N.; Daniels, R. G.; Auditor, M. T. M.; Hilvert, D. Nature 1995, 373, 228.
39. Kemp, D. S.; Cox, D. D.; Paul, K. G. J. Am. Chem. Soc. 1975, 97, 7312.
40. Stewart, J. D.; Benkovic, S. J. Nature 1995, 375, 388.
41. Shevlin, G. S.; Hilton, S.; Janda, K. D. Bioorg. Med. Chem. Lett. 1994, 4, 297.
42. Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812.
43. Whitcombe, M. J.; Rodriguez, M. E.; Villar, P.; Vulfson, E. J. Am. Chem. Soc. 1995, 117, 7105.
44. (a) Kempe, M.; Mosbach, K. J. Chromatogr, 1995, 691, 317.
45. (b) Kempe, M.; Mosbach, K. Int. J. Peptide Protein Res. 1994, 44, 603.
46. (c) Ramström, 0.; Nicholls, I. A.; Mosbach, K. Tetrahedron A 1994, 4, 649.
47. (d) Sellergren, B. Ph.D. Thesis, University of Lund, Sweden, 1988.
48. (e) Andersson, L. I. Ph.D. Thesis, University of Lund, Sweden, 1990.
49. (f) Norrlöw, O. Ph.D. Thesis, University of Lund, Sweden, 1986.
50. (g) Kempe, M. Ph.D. Thesis, University of Lund, Sweden, 1994.
51. (h) Fischer, L; Müller, R.; Ekberg, B.; Mosbach K. J. Am. Chem. Soc. 1991, 113, 9358.
52. (a) Hunter, L. Prog. Stereochem. 1954, 1, 222.
53. (b) Pimentel, G. C.; McClellan, A. I. The Hydrogen Bond; W. H. Freeman: New York, 1960.
54. Sellergren, B.; Shea, K. J. J. Chromatogr. 1993, 635, 31.
55. (a) Tao Y.; Ho, T. J. Chem. Soc., Chem. Commun. 1988, 417.
56. (b) Norrlöw, 0.; Månsson, M. O.; Mosbach, K. J. Chromatogr. 1987, 396, 374.
57. Wulff, G.; Heide, B.; Helfmeier, G. J. Am. Chem. Soc. 1986, 108, 1089.
58. Wulff, G.; Heide, B.; Helfmeier, G. React. Polym. 1987, 6, 299.
59. Adamson, A. W. Physical Chemistry of Surfaces; John Wiley & Sons: Toronto, 1976.
60. Sellergren, B. Makromol. Chem. 1989, 190, 2703.
61. Sellergren, B.; Shea, K. J. J. Chromatogr. 1995, 690, 29.
62. Andersson, L. I.; Müller, R.; Vlatakis, G.; Mosbach, K. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 4788.
63. Shea, K. J.; Sasaki, D. Y. J. Am. Chem. Soc. 1991, 113, 4109.
64. Sellergren, B. Chirality 1989, 1, 63.
65. Mosbach, K. Protein Engr. 1995, 8 (supplement), 54.
66. Andersson, L. I.; Nicholls, I. A.; Mosbach, K. ACS Symp. Ser. 1995, 586, 89.
67. Vlatakis, G.; Andersson, L. I.; Müller, R.; Mosbach, K. Nature 1993, 367, 645.
68. Levine, I. N. Physical Chemistry, 3rd ed.; McGraw Hill: New York, 1988.
69. Jencks, W. P. Catalysis in Chemistry and Enzymology; Dover: New York, 1969.
70. (a) Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
71. (b) Lewis, E. Techniques of Chemistry Volume VI, 3rd ed.; John Wiley & Sons: New York, 1973.
72. 4 in the enthalpy of reaction calculation, due to the fact that MOPAC6 and AM1 are not able to accommodate Li-containing molecules. We note that although the absolute magnitudes of the enthalpies calculated with this method may not be correct, especially for reactions conducted in aqueous media, it is important to emphasize that only the relative trends in the enthalpies with respect to exothermicity are significant for the purpose of evaluating the merit of the Hammond postulate in predicting the plausability of conducting a particular reaction on an imprinted material.
73. (b) Mayo, S. L.; Olafson, B. D.; Goddard III, W. A. J. Phys. Chem. 1990, 94, 8897.
74. Hilvert, D. Curr. Op. Struct. Biol. 1994, 4, 612.
75. Hsieh, L. C.; Yonkovich, S.; Kochersperger, L.; Schultz, P. G. Science 1993, 260, 337.
76. Leonhardt, A.; Mosbach, K. React. Polym. 1987, 6, 286.
77. Robinson, D.; Mosbach, K. J. Chem. Soc., Chem. Commun. 1989, 969.
78. Ohkubo, K.;Urata, Y.; Hirota, S.; Honda, Y.; Fujishita, Y.; Sagawa, T. J. Mol. Catal. 1994, 93, 189.
79. Ohkubo, K.; Urata, Y.; Hirota, S.; Honda, Y.; Sagawa, T. J. Mol. Catal. 1994, 87, L21.
80. Andersson, L. I.; Mosbach, K. Makromol. Chem. Rapid Commun. 1989, 10, 491.
81. Motomura, T.; Inoue, K.; Kobayashi, K.; Aoyama, Y. Tetrahedron Lett. 1991, 32, 4757.
82. (a) Ohkubo, K.; Urata, Y.; Hirota, S.; Funakoshi, Y.; Sagawa, T.; Usui, S.; Yoshinaga, K. J. Mol. Catal. A 1995, 101, L111.
83. (b) Reference 68a reports the difference in the activation free energies between the most catalytically active polymer (TP1') and the uncatalyzed reaction (none) to be 6.4 kcal/mol. This corresponds to a relative rate increase of more than 41 300 for TP1' over none at 303 K, which is significantly larger than the reported experimentally measured value of 3.7.
84. Müller, R.; Andersson, L. I.; Mosbach, K. Makromol. Chem. Rapid Commun. 1993, 14, 637.
85. Beach, J. V.; Shea, K. J. J. Am. Chem. Soc. 1994, 116, 379.
86. Shokat, K. M.; Leumann, C. J.; Sugasawara, R.; Schultz, P. G. Nature 1989, 338, 269.
87. Damen, J.; Neckers, D. C. J. Am. Chem. Soc. 1980, 102, 3265.
88. Wulff, G.; Vietmeier, J. Makromol. Chem. 1989, 190, 1727.
89. Byström, S.; Börje, A.; Akermark, B. J. Am. Chem. Soc. 1993, 115, 2081.
90. Sellergren, B.; Shea, K. J. Tetrahedron A 1994, 8, 1403.
91. Martin, M. T.; Angeles, T. S.; Sugasawara, R.; Aman, N.; Napper, A. D.; Darsley, M. J.; Sanchez, R. I.; Booth, P.; Titmas, R. C. J. Am. Chem. Soc. 1994, 116, 6508.
92. (a) Shea, K. J.; Thompson, E. A. J. Org. Chem. 1978, 43, 4253.
93. (b) Shea, K. J.; Thompson, E. A.; Pandey, S. D.; Beauchamp, P. S. J. Am. Chem. Soc. 1980, 102, 3149.
94. Mathew, J.; Buchart, O. Bioconjugate Chem. 1995, 6, 524.
95. Schwanghart, A.-D.; Backmann, W.; Blasche, G. Chem. Ber. 1977, 110, 778.
96. Andersson, L. I.; Sellergren, B.; Mosbach, K. Tetrahedron Lett. 1984, 25, 5211.
97. Morihara, K.; Kurihara, S.; Suzuki, J. Bull. Chem. Soc. Jpn. 1988, 61, 3991.
98. (a) Morihara, K.; Nishihata, E.; Kojima, M.; Miyake, S. Bull. Chem. Soc. Jpn. 1988, 61, 3999.
99. (b) Morihara, K.; Tanako, E.; Takeuguchi, Y.; Miyazaki, K.; Yamamoto, N.; Sagawa Y.; Kawamoto, E.; Shimada, T. Bull. Chem. Soc. Jpn. 1989, 62, 499.
100. Shimada, T.; Kiyoko, N.; Morihara, K. Bull. Chem. Soc. Jpn. 1992, 65, 954.
101. (a) Morihara, K.; Doi, S.; Takiguchi, M.; Shimada, T. Bull. Chem. Soc. Jpn. 1993, 66, 2977.
102. (b) Morihara, K.; Iijima, T.; Usui, H.; Shimada, T. Bull. Chem. Soc. Jpn. 1993, 66, 3047.
103. (c) Morihara, K.; Nishihata, E.; Kojima, M.; Miyake, S. Bull. Chem. Soc. Jpn. 1993, 66, 906.
104. Shimada, T.; Kurazono, R.; Morihara, K. Bull. Chem. Soc. Jpn. 1993, 66, 836.
105. (a) Matsuishi, T.; Shimada, T.; Morihara, K. Bull. Chem. Soc. Jpn. 1994, 67, 748.
106. (b) Morihara, K.; Takiguchi, M.; Shimada, T. Bull. Chem. Soc. Jpn. 1994, 67, 1078.
107. (c) Shimada, T.; Horose, R.; Morihara, K. Bull. Chem. Soc. Jpn. 1994, 67, 227.
108. Morihara, K.; Kurokawa, M.; Kamata, Y.; Shimada, T. J. Chem. Soc., Chem. Commun. 1992, 358.
109. Bernhard, S.; Gutfreund, H. Proceedings of the International Symposium on Enzyme Chemistry, Tokyo and Kyoto, 1957.
110. Hamilton, C. L.; Niemann, C.; Hammond, G. S. Proc. Natl. Acad. Sci. U.S.A. 1966, 55, 664.
111. Heilmann, J.; Maier, W. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 471.
112. Ahmad, W. R.; Davis, M. E. Catal. Lett., in press.
113. Napper, A. D.; Benkovic, S. J.; Tramontano, A.; Lerner, R. A. Science 1987, 23, 1041.
114. Heilmann, J.; Maier, W. F. Z. Naturforsch. B 1995, 50, 460.
115. Davis, M. E. Ind. Eng. Chem. Res. 1991, 30, 1675.
116. Venuto, P. B. Microporous Mater. 1994, 2, 297.
117. Davis, M. E.; Lobo, R. F. Chem. Mater. 1992, 4, 756.
118. Davis, M. E. Acc. Chem. Res. 1993, 26, 111.
119. Csicsery, S. M. Zeolites 1984, 4, 202.
120. Weisz, P. B.; Frilette, V. J.; Maatman, R. W.; Mower, E. B. J. Catal. 1962, 1, 307.
121. Anderson, M. W.; Klinowski, J. Nature 1989, 339, 220.
122. Kucherov, A. V.; Slinkin, A. A.; Gitis, K. M.; Isagulants, G. V. Catal. Lett. 1988, 1, 311.
123. Khouw, C. B.; Davis, M. E. ACS Symp. Ser. 1993, 517, 206.
124. Perego, G.; Bellussi, C.; Corno, C. Taramasse, M.; Buonomo, F. Stud. Sur. Sci. Catal. 1986, 28, 129.
125. Notari, B. Stud. Sur. Sci. Catal. 1988, 37, 413.
126. Khouw, C. B.; Dartt, C. B.; Labinger, J. A.; M. E. Davis J. Catal. 1994, 149, 195.
127. Li, H. X.; Annen, M. J.; Chen, C. Y.; Arhancet, J. P.; Davis, M. E. J. Mater. Chem. 1991, 1, 79.
128. (a) Burkett, S. L.; Davis, M. E. J. Phys. Chem. 1994, 98, 4647.
129. (b) Burkett, S. L.; Davis, M. E. Chem. Mater. 1995, 7, 920.
130. (c) Burkett, S. L.; Davis, M. E. Chem. Mater. 1995, 7, 1453.
131. Helmkamp, M. M.; Davis, M. E. Annu. Rev. Mater. Sci. 1995, 25, 161.
132. Gies, H.; Marier, B. Zeolites 1992, 12, 42.
133. (a) Iton, L. E.; Trouw, F.; Brun, T. O.; Epperson, J. E.; White, J. W.; Henderson, S. J. Langmuir 1992, 8, 1045.
134. (b) Dokter, W. H.; van Garderen, H. F.; Beelen, T. P. M.; van Santen, R. A.; Bras, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 73.
135. Regev, O.; Cohen, Y.; Kahet, E.; Talmon, Y. Zeolites 1994, 14, 314.
136. Davis, M. E. Stud. Surf. Sci. Catal. 1995, 97, 35.
137. Lobo, R. F.; Zones, S. I.; Davis, M. E. J. Inclus. Phenom. 1995, 47, 21.
138. (a) Zones, S. I.; Olmstead, M. N.; Santilli, D. S. J. Am. Chem. Soc. 1992, 164, 4195.
139. (b) Lobo, R. F.; Pan, M.; Chan, I.; Medrud, R. C.; Zones, S. I.; Crozier, P. A.; Davis, M. E. J. Phys. Chem. 1994, 98, 12040.
140. Schmitt, K. O.; Kennedy, G. J. Zeolites 1994, 14, 635.
141. Li, H. X.; Camblor, M. A.; Davis, M. E. Microporous Mater. 1994, 3, 117.