Directed evolution of enantioselective hybrid catalysts: a novel concept in asymmetric catalysis

Tetrahedron

Volumn 63, Issue 28, 2007, Pages 6404-6414

  Reetz, Manfred T ^a   Rentzsch, Martin ^a   Pletsch, Andreas ^a   Maywald, Matthias ^a   Maiwald, Peter ^a   Peyralans, Jérôme J P ^a   Maichele, Andrea ^a   Fu, Yu ^a   Jiao, Ning ^a   Hollmann, Frank ^a   Mondière, Régis ^a   Taglieber, Andreas ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric catalysis; Directed evolution; Enzymes; Hydrogenation

Indexed keywords

LIGAND; TRANSITION ELEMENT;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; ENANTIOSELECTIVITY; ENZYME MECHANISM; GENE EXPRESSION; GENE MUTATION; GENETIC SCREENING; HYBRID; MUTAGENESIS; MUTANT; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 34249301759     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.177     Document Type: Article

References (150)

1. Knowles W.S. Angew. Chem. 114 (2002) 2096-2107
2. Angew. Chem., Int. Ed. 41 (2002) 1998-2007
3. Noyori R. Angew. Chem. 114 (2002) 2108-2123
4. Angew. Chem., Int. Ed. 41 (2002) 2008-2022
5. Sharpless K.B. Angew. Chem. 114 (2002) 2126-2135
6. Angew. Chem., Int. Ed. 41 (2002) 2024-2032
7. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vols. I-III (1999), Springer, Berlin
8. Reviews of organocatalytic reactions:
9. Lelais G., and MacMillan D.W.C. Aldrichimica Acta 39 (2006) 79-87
10. Seayad J., and List B. Org. Biomol. Chem. 3 (2005) 719-724
11. List B. Tetrahedron 58 (2002) 5573-5590
12. In: Berkessel A., and Gröger H. (Eds). Asymmetric Organocatalysis (2004), Wiley-VCH, Weinheim
13. Dalko P.I., and Moisan L. Angew. Chem. 113 (2001) 3840-3864
14. Angew. Chem., Int. Ed. 40 (2001) 3726-3748
15. In: Drauz K., and Waldmann H. (Eds). Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook. 2nd ed. Vols. I-III (2002), VCH, Weinheim
16. In: Faber K. (Ed). Biotransformations in Organic Chemistry. 4th ed. (2000), Springer, Berlin
17. Schmid A., Dordick J.S., Hauer B., Kiener A., Wubbolts M., and Witholt B. Nature (London) 409 (2001) 258-268
18. Koeller K.M., and Wong C.-H. Nature (London) 409 (2001) 232-240
19. Gennari C., and Piarulli U. Chem. Rev. 103 (2003) 3071-3100
20. Dahmen S., and Bräse S. Synthesis (2001) 1431-1449
21. Hoveyda A.H. In: Nicolaou K.C., Hanko R., and Hartwig W. (Eds). Handbook of Combinatorial Chemistry Vol. 2 (2002), Wiley-VCH, Weinheim, Germany 991-1016
22. de Vries J.G., and de Vries A.H.M. Eur. J. Org. Chem. (2003) 799-811
23. Reetz M.T. Angew. Chem. 113 (2001) 292-320
24. Angew. Chem., Int. Ed. 40 (2001) 284-310
25. Francis M.B., and Jacobsen E.N. Angew. Chem. 111 (1999) 987-991
26. Angew. Chem., Int. Ed. 38 (1999) 937-941
27. Berkessel A., and Riedl R. J. Comb. Chem. 2 (2000) 215-219
28. Ding K., Du H., Yuan Y., and Long J. Chem.-Eur. J. 10 (2004) 2872-2884
29. Reetz M.T., Sell T., Meiswinkel A., and Mehler G. Angew. Chem. 115 (2003) 814-817
30. Angew. Chem., Int. Ed. 42 (2003) 790-793
31. Reetz M.T. Chim. Oggi 21 (2003) 5-8
32. Reetz M.T., and Li X. Tetrahedron 60 (2004) 9709-9714
33. Reetz M.T., Mehler G., Meiswinkel A., and Sell T. Tetrahedron: Asymmetry 15 (2004) 2165-2167
34. Reetz M.T., Ma J.-A., and Goddard R. Angew. Chem. 117 (2005) 416-419
35. Angew. Chem., Int. Ed. 44 (2005) 412-415
36. Reetz M.T. In: Ward M.D. (Ed). Comprehensive Coordination Chemistry II Vol. 9 (2004), Elsevier, Amsterdam 509-548
37. Reetz M.T., and Guo H. Beilstein J. Org. Chem. 1 (2005) 3
38. Reetz M.T., and Li X. Angew. Chem. 117 (2005) 3019-3021
39. Angew. Chem., Int. Ed. 44 (2005) 2959-2962
40. Reetz M.T., and Li X. Angew. Chem. 117 (2005) 3022-3024
41. Angew. Chem., Int. Ed. 44 (2005) 2962-2964
42. Reetz M.T., and Surowiec M. Heterocycles 67 (2006) 567-574
43. Peña D., Minnaard A.J., Boogers J.A.F., de Vries A.H.M., de Vries J.G., and Feringa B.L. Org. Biomol. Chem. 1 (2003) 1087-1089
44. Hoen R., Boogers J.A.F., Bernsmann H., Minnaard A.J., Meetsma A., Tiemersma-Wegman T.D., de Vries A.H.M., de Vries J.G., and Feringa B.L. Angew. Chem. 117 (2005) 4281-4284
45. Angew. Chem., Int. Ed. 44 (2005) 4209-4212
46. Yoon T.P., and Jacobsen E.N. Science 299 (2003) 1691-1693
47. Klibanov A.M. Nature (London) 409 (2001) 241-246
48. In: Liese A., Seelbach K., and Wandrey C. (Eds). Industrial Biotransformations (2006), Wiley-VCH, Weinheim
49. Imanaka T., and Atomi H. In: Drauz K., and Waldmann H. (Eds). Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook Vol. 1 (2002), Wiley-VCH, Weinheim 67-95
50. Cedrone F., Ménez A., and Quéméneur E. Curr. Opin. Struct. Biol. 10 (2000) 405-410
51. Harris J.L., and Craik C.S. Curr. Opin. Chem. Biol. 2 (1998) 127-132
52. Kazlauskas R.J. Curr. Opin. Chem. Biol. 4 (2000) 81-88
53. Li Q.-S., Schwaneberg U., Fischer M., Schmitt J., Pleiss J., Lutz-Wahl S., and Schmid R.D. Biochim. Biophys. Acta 1545 (2001) 114-121
54. Reetz M.T., Zonta A., Schimossek K., Liebeton K., and Jaeger K.-E. Angew. Chem. 109 (1997) 2961-2963
55. Angew. Chem., Int. Ed. 36 (1997) 2830-2832
56. Reetz, M. T.; Zonta, A.; Schimossek, K.; Liebeton, K.; Jäger, K.-E. Patent EP 1,002,100 B1, 2003.
57. Schimossek, K. Dissertation, Ruhr-Universität Bochum, 1998.
58. Reetz M.T. Pure Appl. Chem. 71 (1999) 1503-1509
59. In: Arnold F.H., and Georgiou G. (Eds). Directed Enzyme Evolution: Screening and Selection Methods Vol. 230 (2003), Humana, Totowa, New Jersey, NJ
60. In: Brakmann S., and Johnsson K. (Eds). Directed Molecular Evolution of Proteins (or How to Improve Enzymes for Biocatalysis) (2002), Wiley-VCH, Weinheim
61. In: Brakmann S., and Schwienhorst A. (Eds). Evolutionary Methods in Biotechnology (Clever Tricks for Directed Evolution) (2004), Wiley-VCH, Weinheim, Germany
62. Taylor S.V., Kast P., and Hilvert D. Angew. Chem. 113 (2001) 3408-3436
63. Angew. Chem., Int. Ed. 40 (2001) 3310-3335
64. Powell K.A., Ramer S.W., del Cardayré S.B., Stemmer W.P.C., Tobin M.B., Longchamp P.F., and Huisman G.W. Angew. Chem. 113 (2001) 4068-4080
65. Angew. Chem., Int. Ed. 40 (2001) 3948-3959
66. Rubin-Pitel S.B., and Zhao H. Comb. Chem. High Throughput Screen. 9 (2006) 247-257
67. Kaur J., and Sharma R. Crit. Rev. Biotechnol. 26 (2006) 165-199
68. Reetz M.T. Angew. Chem. 114 (2002) 1391-1394
69. Angew. Chem., Int. Ed. 41 (2002) 1335-1338
70. Reetz M.T. In: Reymond J.-L. (Ed). Enzyme Assays-High-throughput Screening, Genetic Selection and Fingerprinting (2006), Wiley-VCH, Weinheim 41-76
71. Reetz M.T., Wilensek S., Zha D., and Jaeger K.-E. Angew. Chem. 113 (2001) 3701-3703
72. Angew. Chem., Int. Ed. 40 (2001) 3589-3591
73. Reetz M.T. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5716-5722
74. Bocola M., Otte N., Jaeger K.-E., Reetz M.T., and Thiel W. ChemBioChem 5 (2004) 214-223
75. Reetz M.T., Puls M., Carballeira J.D., Vogel A., Jaeger K.-E., Eggert T., Thiel W., Bocola M., and Otte N. ChemBioChem 8 (2007) 106-112
76. Reetz M.T., Wang L.-W., and in part Bocola M. Angew. Chem. 118 (2006) 1258-1263 Erratum, 2556
77. Angew. Chem., Int. Ed. 45 (2006) 1236-1241 Erratum, 2494
78. Reetz M.T., Carballeira J.D., and Vogel A. Angew. Chem. 118 (2006) 7909-7915
79. Angew. Chem., Int. Ed. 45 (2006) 7745-7751
80. Reetz M.T., and Carballeira J.D. Nat. Protoc. 2 (2007) 891-903
81. Reetz M.T., Bocola M., Carballeira J.D., Zha D., and Vogel A. Angew. Chem. 117 (2005) 4264-4268
82. Angew. Chem., Int. Ed. 44 (2005) 4192-4196
83. Reetz M.T., Carballeira J.D., Peyralans J.J.-P., Höbenreich H., Maichele A., and Vogel A. Chem.-Eur. J. 12 (2006) 6031-6038
84. Reetz M.T. In: Gates B.C., and Knözinger H. (Eds). Comprehensive Review of Directed Evolution of Enantioselective Enzymes. Advances in Catalysis Vol. 49 (2006), Elsevier, San Diego, CA 1-69
85. Parshall G.W., and Ittel S.D. Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes. 2nd ed. (1992), Wiley, New York, NY
86. Cornils B., and Herrmann W.A. Aqueous-Phase Organometallic Catalysis, Concepts and Applications. 2nd ed. (2004), Wiley-VCH, Weinheim
87. Reetz M.T., Rentzsch M., Pletsch A., and Maywald M. Chimia 56 (2002) 721-723
88. Reetz M.T. Tetrahedron 58 (2002) 6595-6602
89. Reetz, M. T. Patent WO 92,18645, 2001.
90. Maiwald, P. Dissertation, Ruhr-Universität Bochum, 2001.
91. Qi D., Tann C.-M., Haring D., and Distefano M.D. Chem. Rev. 101 (2001) 3081-3111
92. Polgar L., and Bender M.L. J. Am. Chem. Soc. 88 (1966) 3153-3154
93. Schultz P.G. Science (Washington, D.C.) 240 (1988) 426-433
94. Khumtaveeporn K., DeSantis G., and Jones J.B. Tetrahedron: Asymmetry 10 (1999) 2563-2572
95. Smith H.B., and Hartman F.C. J. Biol. Chem. 263 (1988) 4921-4925
96. Nicholas K.M., Wentworth Jr. P., Harwig C.W., Wentworth A.D., Shafton A., and Janda K.D. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 2648-2653
97. Hamachi I., and Shinkai S. Eur. J. Org. Chem. (1999) 539-549
98. Lu Y. Curr. Opin. Chem. Biol. 9 (2005) 118-126
99. Lu Y., and Valentine J.S. Curr. Opin. Struct. Biol. 7 (1997) 495-500
100. Lu Y., Berry S.M., and Pfister T.D. Chem. Rev. 101 (2001) 3047-3080
101. Barker P.D. Curr. Opin. Struct. Biol. 13 (2003) 490-499 See also:
102. Kaiser E.T. Angew. Chem. 100 (1988) 945-955
103. Angew. Chem., Int. Ed. Engl. 27 (1988) 913-922
104. Hilvert D., and Kaiser E.T. Biotechnol. Genet. Eng. Rev. 5 (1987) 297-318
105. de Vries J.G., and Lefort L. Chem.-Eur. J. 12 (2006) 4722-4734
106. Kruithof C.A., Casado M.A., Guillena G., Egmond M.R., van der Kerk-van Hoof A., Heck A.J.R., Klein Gebbink R.J.M., and van Koten G. Chem.-Eur. J. 11 (2005) 6869-6877
107. Panella L., Broos J., Jin J., Fraaije M.W., Janssen D.B., Jeronimus-Stratingh M., Feringa B.L., Minnaard A.J., and de Vries J.G. Chem. Commun. (Cambridge) (2005) 5656-5658
108. Davis B.G. Curr. Opin. Biotechnol. 14 (2003) 379-386
109. Eckermann A.L., Barker K.D., Hartings M.R., Ratner M.A., and Meade T.J. J. Am. Chem. Soc. 127 (2005) 11880-11881
110. Ward T.R. Chem.-Eur. J. 11 (2005) 3798-3804
111. Wilson M.E., and Whitesides G.M. J. Am. Chem. Soc. 100 (1978) 306-307 See also:
112. Lin C.-C., Lin C.-W., and Chan A.S.C. Tetrahedron: Asymmetry 10 (1999) 1887-1893
113. Reetz M.T., Peyralans J.J.-P., Maichele A., Fu Y., and Maywald M. Chem. Commun. (Cambridge) (2006) 4318-4320
114. Collot J., Gradinaru J., Humbert N., Skander M., Zocchi A., and Ward T.R. J. Am. Chem. Soc. 125 (2003) 9030-9031
115. Thomas C.M., and Ward T.R. Chem. Soc. Rev. 34 (2005) 337-346
116. Bayer E.A., Ben-Hur H., and Wilchek M. Methods Enzymol. 184 (1990) 80-89
117. Thompson L.D., and Weber P.C. Gene 136 (1993) 243-246
118. Sano T., and Cantor C.R. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 142-146
119. Wu S.C., Qureshi M.H., and Wong S.L. Protein Expr. Purif. 24 (2002) 348-356
120. Wu S.-C., and Wong S.-L. Appl. Environ. Microbiol. 68 (2002) 1102-1108
121. Gallizia A., de Lalla C., Nardone E., Santambrogio P., Brandazza A., Sidoli A., and Arosio P. Protein Expr. Purif. 14 (1998) 192-196
122. Studier F.W. Protein Expr. Purif. 41 (2005) 207-234
123. Maywald, M. Dissertation, Ruhr-Universität Bochum, 2005.
124. Pletsch, A. Dissertation, Ruhr-Universität Bochum, 2004.
125. Rentzsch, M. Dissertation, Ruhr-Universität Bochum, 2004.
126. Weber P.C., Ohlendorf D.H., Wendoloski J.J., and Salemme F.R. Science 243 (1989) 85-88
127. Bosley A.D., and Ostermeier M. Biomol. Eng. 22 (2005) 57-61
128. Patrick W.M., and Firth A.E. Biomol. Eng. 22 (2005) 105-112
129. Kamphuis I.G., Kalk K.H., Swarte M.B.A., and Drenth J. J. Mol. Biol. 179 (1984) 233-256
130. Reetz M.T., and Jiao N. Angew. Chem. 118 (2006) 2476-2479
131. Angew. Chem., Int. Ed. 45 (2006) 2463-2466
132. Peters T. All about Albumin: Biochemistry, Genetics and Medical Applications (1996), Academic, San Diego, CA
133. Zunszain P.A., Ghuman J., Komatsu T., Tsuchida E., and Curry S. BMC Struct. Biol. 3 (2003) 6
134. Mahammed A., and Gross Z. J. Am. Chem. Soc. 127 (2005) 2883-2887
135. Mahammed A., Gray H.B., Weaver J.J., Sorasaenee K., and Gross Z. Bioconjugate Chem. 15 (2004) 738-746
136. Otto S., and Engberts J.B.F.N. J. Am. Chem. Soc. 121 (1999) 6798-6806
137. Otto S., Boccaletti G., and Engberts J.B.F.N. J. Am. Chem. Soc. 120 (1998) 4238-4239
138. Roelfes G., and Feringa B.L. Angew. Chem. 117 (2005) 3294-3296
139. Angew. Chem., Int. Ed. 44 (2005) 3230-3232
140. Barr K.A., Hopkins S.A., and Sreekrishna K. Pharm. Eng. 12 (1992) 48-52
141. Ohtani W., Nawa Y., Takeshima K., Kamuro H., Kobayashi K., and Ohmura T. Anal. Biochem. 256 (1998) 56-62
142. Taglieber, A. Projected Dissertation, Ruhr-Universität Bochum, 2007.
143. 26c
144. Nuzzo R.G., Haynie S.L., Wilson M.E., and Whitesides G.M. J. Org. Chem. 46 (1981) 2861-2867
145. The widely used QuikChange protocol (QuikChange site-directed mutagenesis kit. Instruction Manual, 2003, Stratagene, La Jolla, CA) is based on a number of previous publications. These and other developments have been reviewed in:
146. Dominy C.N., and Andrews D.W. In: Casali N., and Preston A. (Eds). Methods in Molecular Biology Vol. 235 (2003), Humana, Totowa, NJ 209-223
147. Vandeyar M.A., Weiner M.P., Hutton C.J., and Batt C.A. Gene 65 (1988) 129-133
148. Kirsch R.D., and Joly E. Nucleic Acids Res. 26 (1998) 1848-1850
149. Annis D.A., and Jacobsen E.N. J. Am. Chem. Soc. 121 (1999) 4147-4154
150. Rich D.H., Gesellchen P.D., Tong A., Cheung A., and Buckner C.K. J. Med. Chem. 18 (1975) 1004-1010