Artificial metalloenzymes: Combining the best features of homogeneous and enzymatic catalysis

Synlett

Volumn , Issue 20, 2009, Pages 3225-3236

  Pordea, Anca ^a   Ward, Thomas R ^a,b  

^a UNIVERSITY OF NEUCHÂTEL   (Switzerland)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Asymmetric catalysis; Biomimetic synthesis; Combinatorial chemistry; Enzymes; Homogeneous catalysis

Indexed keywords

ALKENE; BIOTIN; KETONE; METALLOENZYME; METALLOPROTEIN; STREPTAVIDIN; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ALDOL REACTION; ALKYLATION; ASYMMETRIC CATALYSIS; COMBINATORIAL CHEMISTRY; DIELS ALDER REACTION; HYDROFORMYLATION; HYDROGENATION; HYDROLYSIS; OXIDATION; REVIEW; SITE DIRECTED MUTAGENESIS; SYNTHESIS;

EID: 72149091173     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218305     Document Type: Review

References (102)

1. Pauling L, Nature 1948 161 707
2. Vogl E M., Gröger H, Shibasaki M, Angew. Chem. Int. Ed. 1999 38 1570
3. Koeller K M., Wong C H., Nature 2001 409 232
4. Schmid A, Dordick J S., Hauer B, Kiener A, Wubbolts M, Witholt B, Nature 2001 409 258
5. Toscano M D., Woycechowsky K J., Hilvert D, Angew. Chem. Int. Ed. 2007 46 3212
6. Sylvestre J, Chautard H, Cedrone F, Delcourt M, Org. Process Res. Dev. 2006 10 562
7. Arnold F H., Volkov A A., Curr. Opin. Chem. Biol. 1999 3 54
8. Reetz M T., Proc. Natl. Acad. Sci. U.S.A. 2004 101 5716
9. Kaur J, Sharma R, Crit. Rev. Biotechnol. 2006 26 165
10. Bershtein S, Tawfik D S., Curr. Opin. Chem. Biol. 2008 12 151
11. Reetz M T., Kahakeaw D, Sanchis J, Mol. BioSyst. 2009 5 115
12. Wang L, Schultz P G., Angew. Chem. Int. Ed. 2005 44 34
13. Qi D, Tann C M., Haring D, Distefano M D., Chem. Rev. 2001 101 3081
14. Lu Y, Curr. Opin. Chem. Biol. 2005 9 118
15. Thomas C M., Ward T R., Chem. Soc. Rev. 2005 34 337
16. Lu Y, Inorg. Chem. 2006 45 9930
17. Letondor C, Ward T R., ChemBioChem 2006 7 1845
18. Steinreiber J, Ward T R., Coord. Chem. Rev. 2008 252 751
19. Wilson M E., Whitesides G M., J. Am. Chem. Soc. 1978 100 306
20. Hilvert D, Curr. Opin. Struct. Biol. 1994 4 612
21. Schultz P G., Lerner R A., Science 1995 269 1835
22. Wentworth P, Janda K D., Curr. Opin. Chem. Biol. 1998 2 138
23. Damborsky J, Brezovsky J, Curr. Opin. Chem. Biol. 2009 13 26
24. Jiang L, Althoff E A., Clemente F R., Doyle L, Röthlisberger D, Zanghellini A, Gallaher J L., Betker J L., Tanaka F, Barbas C F. III., Hilvert D, Houk K N., Stoddard B L., Baker D, Science 2008 319 1387
25. Röthlisberger D, Khersonsky O, Wollacott A M., Jiang L, DeChancie J, Betker J, Gallaher J L., Althoff E A., Zanghellini A, Dym O, Albeck S, Houk K N., Tawfik D S., Baker D, Nature 2008 453 190
26. Tantillo D J., Chen J, Houk K N., Curr. Opin. Chem. Biol. 1998 2 743
27. Sugimoto T, Matsumura Y, Tanimoto S, Okano M, J. Chem. Soc., Chem. Commun. 1978 926
28. Sugimoto T, Kokubo T, Miayzaki J, Tanimoto S, Okano M, [nl] J. Chem. Soc., Chem. Commun. 1979 402
29. Baba N, Matsumura Y, Sugimoto T, Tetrahedron Lett. 1978 19 4281
30. Colonna S, Banfi S, Fontana F, Sommaruga M, J. Org. Chem. 1985 50 769
31. Colonna S, Manfredi A, Annunziata R, Tetrahedron Lett. 1988 29 3347
32. Das P K., Caaveiro J M. M., Luque S, Klibanov [nl]A M., Biotechnol. Bioeng. 2002 78 104
33. Dzyuba S V., Klibanov A M., Tetrahedron: Asymmetry 2004 15 2771
34. Nishijima M, Wada T, Mori T, Pace T C. S., Bohne C, Inoue Y, J. Am. Chem. Soc. 2007 129 3478
35. Kaiser E T., Lawrence D S., Science 1984 226 505
36. Levine H L., Nakagawa Y, Kaiser E T., Biochem. Biophys. Res. Commun. 1977 76 64, Fried H E., Kaiser E T., J. Am. Chem. Soc. 1981 103 182
37. Suckling C J., Zhu L.-M, Bioorg. Med. Chem. Lett. 1993 3 531
38. Kuang H, Brown M L., Davies R R., Young E C., Distefano M D., J. Am. Chem. Soc. 1996 118 10702
39. Wu Z P., Hilvert D, J. Am. Chem. Soc. 1990 112 5647
40. Häring D, Schüler E, Adam W, Saha-Möller C R., Schreier P, J. Org. Chem. 1999 64 832
41. Lee H S., Schultz P G., J. Am. Chem. Soc. 2008 130 13194
42. Blaser H.-U, Malan C, Pugin B, Spindler F, Steiner H, Studer M, Adv. Synth. Catal. 2003 345 103
43. Collot J, Gradinaru J, Humbert N, Skander M, Zocchi A, Ward T R., J. Am. Chem. Soc. 2003 125 9030
44. Lin C.-C, Lin C.-W, Chan A S. C., Tetrahedron: Asymmetry 1999 10 1887
45. Skander M, Humbert N, Collot J, Gradinaru J, Klein G, Loosli A, Sauser J, Zocchi A, G ilardoni F, Ward T R., J. Am. Chem. Soc. 2004 126 14411
46. Reetz M T., Peyeralans J J.-P, Maichele A, Fu Y, Maywald M, Chem. Commun. 2006 4318
47. Klein G, Humbert N, Gradinaru J, Ivanova A, Gilardoni F, Rusbandi U E., Ward T R., Angew. Chem. Int. Ed. 2005 44 7764
48. Skander M, Malan C, Ivanova A, Ward T R., Chem. Commun. 2005 4815
49. Rusbandi U E., Lo C, Skander M, Ivanova A, Creus M, Humbert N, Ward T R., Adv. Synth. Catal. 2007 349 1923
50. Yamaguchi H, Hirano T, Kiminami H, Taura D, Harada A, Org. Biomol. Chem. 2006 4 3571
51. Panella L, Broos J, Jin J, Fraaije M W., Janssen D B., Jeronimus-Stratingh M, Feringa B L., Minnaard A J., deVries J G., Chem. Commun. 2005 5656
52. Faber K, Biotransformations in Organic Chemistry 5th ed. Springer Berlin 2004 177
53. Kroutil W, Mang H, Edegger K, Faber K, Curr. Opin. Chem. Biol. 2004 8 120
54. Moore J C., Pollard D J., Kosjek B, Devine P N., Acc. Chem. Res. 2007 40 1412
55. Ikariya T, Blacker A J., Acc. Chem. Res. 2007 40 1300
56. Letondor C, Humbert N, Ward T R., Proc. Natl. Acad. Sci. U.S.A. 2005 102 4683
57. Letondor C, Pordea A, Humbert N, Ivanova A, Mazurek S, Novic M, Ward T R., J. Am. Chem. Soc. 2006 128 8320
58. Pordea A, Creus M, Letondor C, Ivanova A, Ward T R., Inorg. Chim. Acta 2009 in press; doi: 10.1016/j.ica.2009.02.001
59. Pordea A, Ward T R., Chem. Commun. 2008 4239
60. Creus M, Pordea A, Rossel T, Sardo A, Letondor C, Ivanova A, LeTrong I, Stenkamp R E., Ward T R., Angew. Chem. Int. Ed. 2008 47 1400
61. Modern Oxidation Methods, Bäckvall J.-E, Wiley-VCH Weinheim 2004
62. Mahammed A, Gross Z, J. Am. Chem. Soc. 2005 127 2883
63. DeLauzon S, Quilez R, Lion L, Desfosses B, Desfosses B, Lee I, Sari M.-A, Benkovic S J., Mansuy D, Mahy J.-P, Eur. J. Biochem. 1998 257 121
64. Ricoux R, Lukowska E, Pezzotti F, Mahy J.-P, Eur. J. Biochem. 2004 271 1277
65. Ohashi M, Koshiyama T, Ueno T, Yanase M, Fujii H, Watanabe Y, Angew. Chem. Int. Ed. 2003 42 1005
66. Ueno T, Koshiyama T, Ohashi M, Kondo K, Kono M, Suzuki A, Yamane T, Watanabe Y, J. Am. Chem. Soc. 2005 127 6556
67. Carey J R., Ma S K., Pfister [nl]T D., Garner D K., Kim H K., Abramite J A., Wang Z, Guo Z, Lu Y, J. Am. Chem. Soc. 2004 126 10812
68. Rousselot-Pailley P, Bochot C, Marchi-Delapierre C, Jorge-Robin A, Martin L, Fontecilla-Camps J C., Cavazza C, Ménage S, ChemBioChem 2009 10 545
69. Pordea A, Mathis D, Ward T R., J. Organomet. Chem. 2009 694 930
70. vandeVelde F, Könemann L, vanRantwijk F, Sheldon R A., Chem. Commun. 1998 1891
71. vandeVelde F, Könemann L, vanRantwijk F, Sheldon R A., Biotechnol. Bioeng. 2000 67 87
72. vandeVelde F, Arends I W., Sheldon R A., J. Inorg. Biochem. 2000 80 81
73. Pordea A, Creus M, Panek J, Duboc C, Mathis D, Novic M, Ward T R., J. Am. Chem. Soc. 2008 130 8085
74. Kokubo T, Sugimoto T, Uchida T, Tanimoto S, Okano M, J. Chem. Soc., Chem. Commun. 1983 769
75. Okrasa K, Kazlauskas R J., Chem. Eur. J. 2006 12 1587
76. Fernández-G acio A, Codina A, Fastrez J, Riant O, Soumillion P, ChemBioChem 2006 7 1013
77. Thomas C M., Letondor C, Humbert N, Ward T R., [nl]J. Organomet. Chem. 2005 690 4488
78. Chen C H., Sigman D S., Science 1987 237 1197
79. Ebright R H., Ebright Y W., Pendergrast P S., Gunasekera A, Proc. Natl. Acad. Sci. U.S.A. 1990 87 2882
80. Rana T M., Meares C F., J. Am. Chem. Soc. 1990 112 2457
81. Wu J, Perrin D M., Sigman D S., Kaback H R., Proc. Natl. Acad. Sci. U.S.A. 1995 92 9186
82. Davies R R., Distefano M D., J. Am. Chem. Soc. 1997 119 11643
83. Marchetti M, Mangano G, Paganelli S, Botteghi C, Tetrahedron Lett. 2000 41 3717
84. Bertucci C, Botteghi C, Giunta D, Marchetti M, Paganelli S, Adv. Synth. Catal. 2002 344 556
85. Crobu S, Marchetti M, Sanna G, J. Inorg. Biochem. 2006 100 1514
86. Sijbren O, Engberts J B. F. N., J. Am. Chem. Soc. 1999 121 6798
87. Stocking E M., Williams R M., Angew. Chem. Int. Ed. 2003 42 3078
88. Romesberg F E., Spiller B, Schultz P G., Stevens R C., Science 1998 279 1929
89. Heine A, Stura E A., Yli-Kauhaluoma J T., Gao C, Deng Q, Beno B R., Houk K N., Janda K D., Wilson I A., Science 1998 279 1934
90. Seelig B, Keiper S, Stuhlmann F, Jäschke A, Angew. Chem. Int. Ed. 2000 39 4576
91. Roelfes G, Feringa B L., Angew. Chem. Int. Ed. 2005 44 3230
92. Roelfes G, Boersma A J., Feringa B L., Chem. Commun. 2006 635
93. Boersma A J., Klijn J E., Feringa B L., Roelfes G, J. Am. Chem. Soc. 2008 130 11783
94. Oltra N S., Roelfes G, Chem. Commun. 2008 6039
95. Reetz M T., Jiao N, Angew. Chem. Int. Ed. 2006 45 2416
96. Coquière D, Feringa B L., Roelfes G, Angew. Chem. Int. Ed. 2007 46 9308
97. Dijk E W., Feringa B L., Roelfes G, Tetrahedron: Asymmetry 2008 19 2374
98. Boersma A J., Feringa B L., Roelfes G, Angew. Chem. Int. Ed. 2009 48 3346
99. Shibata N, Yasui H, Nakamura S, Toru T, Synlett 2007 1153
100. Fournier P, Fiammengo R, Jäschke A, Angew. Chem. Int. Ed. 2009 48 4426
101. Pierron J, Malan C, Creus M, Gradinaru J, Hafner I, Ivanova A, Sardo A, Ward T R., Angew. Chem. Int. Ed. 2008 47 701
102. Reetz M T., Rentzsch M, Pletsch A, Taglieber A, Hollmann F, Mondière R J. G., Dickmann N, Hoecker B, Cerrone S, Haeger M C., Sterner R, ChemBioChem 2008 9 552