Technical application of biological principles in asymmetric catalysis

Advances in Biochemical Engineering/Biotechnology

Volumn 92, Issue , 2005, Pages 197-224

  Liese, Andreas ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME;

BIOLOGICAL MODEL; BIOLOGY; BIOTECHNOLOGY; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; ISOMERISM; METABOLISM; METHODOLOGY; REVIEW; TECHNOLOGY;

BIOLOGY; BIOTECHNOLOGY; CATALYSIS; ENZYMES; ISOMERISM; MODELS, BIOLOGICAL; MODELS, CHEMICAL; TECHNOLOGY TRANSFER;

EID: 17144431936     PISSN: 07246145     EISSN: None     Source Type: Book Series    
DOI: 10.1007/b98912     Document Type: Review

References (192)

1. Houghton Mifflin Co. (1992) The American Heritage dictionary of the english language. Houghton Mifflin Co., Boston, MA
2. Nachtigall W (1991) In: Witt R, Lieckfeld C-P (eds) Bionik-patente der natur. Pro Futura Verlag GmbH, München, p 7
3. Anton DL (1998) Chem Eng News 15
4. Kieboom AP, Moulijn J, Leeuwen PWNM, Santen RAv (1999) In: Santen RAv, Moulijn J, Leeuwen PWNM, Averill BA (eds) Catalysis: an integrated approach. Elsevier, Amsterdam, p 3
5. Engels S, Stolz R, Göbel W, Nawrocki F, Nowak A (1989) ABC geschichte der chemie. VEB Deutscher Verlag für Grundstoffindustrie, Leipzig
6. Cornils B, Herrmann WA, Schlögl R, Wong C-H (1999) Catalysis from A to Z: a concise encyclopedia. Wiley-VCH, Weinheim
7. Turner MK (1998) In: Kelly DR (ed) Biotransformations I (Biotechnology), vol 8. Wiley-VCH, Weinheim, p 9ff
8. Enders D, Hoffmann R (1985) Chem Unserer Zeit 19:177
9. Stinson SC (1999) Chem Eng News (22nd of November) 57
10. Pasteur L (1858) CR Acad Sci (Paris) 46:615
11. Sheldon RA (1993) Chirotechnology. Marcel Dekker, New York
12. Neuberg C, Ohle H (1921) Biochem Z 127:326
13. Hildebrandt G, Klavehn W (1932) Deutsches Reichspatent Nr. 584 459
14. Bornscheuer U (2000) In: Rehm H, Reed G, Pühler A, Stadler P (eds) Biotechnology-serie, vol 8b. Wiley-VCH, Weinheim, p 277
15. Peters J (1998) In: Rehm H-J, Reed G, Pühler A, Stadler P (eds) Biotechnology, vol 8a. Wiley-VCH, Weinheim, p 393
16. Liese A, Villela Filho M (1999) Curr Opin Biotech 10:595
17. Patel RN (2001) Adv Synth Catal 343:527
18. Patel RN (2000) Stereoselective biocatalysis. Marcel Dekker, New York
19. Tanaka A, Tosa T, Kobayashi T (1993) Industrial application of immobilized biocatalysts. Marcel Decker, New York
20. Collins AN, Sheldrake GN, Crosby J (1992) Chirality in industry. Wiley, New York
21. Liese A, Seelbach K, Wandrey C (2000) Industrial biotransformations. VCH-Wiley, Weinheim
22. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Nature 409:258
23. Straathof A, Panke S, Schmidt A (2002) Curr Opin Biotech 13:538
24. Thomas SM, DiCosimo R, Nagarajan V (2002) Trend Biotech 20:238
25. Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Stuermer R, Zelinski T (2004) Angew Chem Int Edit 43:788
26. Faber K (2000) Biotransformations in organic synthesis. Springer, Berlin Heidelberg New York
27. Griengl H (2000) Biocatalysis. Springer, Berlin Heidelberg New York
28. Liese A (2002) In: Drauz K, HW (eds) Enzyme catalysis in organic synthesis, 2nd edn, vol 3. VCH-Wiley, Weinheim, p 1419
29. Drauz K, Waldmann H (2002) Enzyme catalysis in organic synthesis. Wiley-VCH, Weinheim
30. Silverman RB (2002) The organic chemistry of enzyme-catalyzed reactions. Academic, San Diego, CA
31. Bommarius A, Riebel B (2004) Biocatalysis: fundamentals and applications. Wiley-VCH, Weinheim
32. Bredig G, Fiske PS (1912) Biochem Z 46:7
33. Wynberg H (1986) Top Stereochem 16:87
34. Cane DE (1990) Chem Rev 90:1089
35. Bunce RA (1995) Tetrahedron 51:13103
36. Mayer SF, Kroutil W, Faber K (2001) Chem Soc Rev 30:332
37. Bruggink A, Schoevaart R, Kieboom T (2003) Org Process Res Dev 7:622
38. Wiese A, Wilms B, Syldatk C, Mattes R, Altenbuchner J (2001) Appl Microbiol Biot 55:750
39. Ragnitz K, Syldatk C, Pietzsch M (2001) Enzyme Microb Tech 28:713
40. Wegman MA, van Langen LM, van Rantwijk F, Sheldon RA (2002) Biotechnol Bioeng 79:356
41. Miyazaki M, Ogino K, Shibue M, Nakamura H, Maeda H (2002) Chem Lett 758
42. Schoevaart R, van Rantwijk F, Sheldon RA (2001) J Org Chem 66:351
43. Schoevaart R, van Rantwijk F, Sheldon RA (2000) J Org Chem 65:6940
44. Scott AI (1994) Synlett 871
45. Roessner CA, Scott AI (1996) Annu Rev Microbiol 50:467
46. Jones JB, Sneddon DW, Higgins W, Lewis AJ (1972) J Chem Soc Chem Commun 856
47. Wichmann R, Wandrey C, Bückmann AF, Kula M-R (1981) Biotechnol Bioeng 23:2789
48. Wong C-H, Whitesides GM (1982) J Org Chem 47:2816
49. Kruse W, Hummel W, Kragl U (1996) Recl Trav Chim Pay B 115:239
50. Mertens R, Greiner L, van den Ban ECD, Haaker HBCM, Liese A (2003) J Mol Catal B-Enzym 24-25:39
51. Zervosen A, Elling L (1996) J Am Chem Soc 118:1836
52. Herrmann G, Ichikawa Y, Wandrey C, Gaeta F, Paulson JC, Wong C-H (1993) Tetrahedron Lett 4:1193
53. Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem 107:453
54. Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem 107:569
55. Brinkmann N, Malissard M, Ramuz M, Römer U, Schumacher T, Berger EG, Elling L, Wandrey C, Liese A (2001) Bioorg Med Chem Lett 11:2503
56. Rentmeister A, Hoh C, Weidner S, Dräger G, Elling L, Liese A, Wandrey C (2004) Biocatal Biotransfor 22:49
57. Blixt O, Paulson JC (2003) Adv Synth Catal 345:687
58. Dudziak G, Zeng S, Berger EG, Gellego RG, Kamerling JP, Kragl U, Wandrey C (1998) Bioorg Med Chem 8:2595
59. Petersen M, Zannetti MT, Fessner W-D (1997) Top Curr Chem 186:87
60. Bulter T, Schumacher T, Namdjou D-J, Gallego RG, Clausen H, Elling L (2001) Chembiochem 2:884
61. Hoh C, Dudziak G, Liese A (2001) Bioorg Med Chem Lett 12:1031
62. Hoffmann N (1996) Chem Unserer Zeit 30:201
63. Endo T, Koizumi S (2001) Adv Synth Catal 343:521
64. Stewart JD (2000) Curr Opin Biotechnol 11:363
65. Rodriguez S, Schroeder KT, Kayser MM, Stewart JD (2000) J Org Chem 65:2586
66. Kataoka M, Rohani LPS, Yamamoto K, Wada M, Kawabata H, Kita K, Yanase H, Shimizu S (1997) Appl Microbiol Biot 48:699
67. Kataoka M, Rohani LPS, Wada M, Kita K, Yanase H, Urabe I, Shimizu S (1998) Biosci Biotech Bioch 62:167
68. Kataoka M, Yamamoto K, Kawabata H, Wada M, Kita K, Yanase H, Shimizu S (1999) Appl Microbiol Biot 51:486
69. Kizaki N, Yasohara Y, Hasegawa J, Wada M, Kataoka M, Shimizu S (2001) Appl Microbiol Biot 55:590
70. Yasohara Y, Kizaki N, Hasegawa J, Wada M, Kataoka M, Shimizu S (2001) Tetrahedron-Asymmet 12:1713
71. Haberland J, Hummel W, Dausmann T, Liese A (2002) Org Process Res Dev 6:458
72. Haberland J, Kriegesmann A, Wolfram E, Hummel W, Liese A (2002) Appl Microbiol Biot 58:595
73. Endo T, Koizumi S (2000) Curr Opin Struct Biol 10:536
74. Tabata K, Koizumi S, Endo T, Ozaki A (2002) Enzyme Microb Tech 30:327
75. Endo T, Koizumi S, Tabata K, Kakita S, Ozaki A (2001) Carbohyd Res 330:439
76. Koizumi S, Endo T, Tabata K, Nagano H, Ohnishi J, Ozaki A (2000) J Ind Microbiol Biot 25:213
77. Endo T, Koizumi S, Tabata K, Ozaki A (2000) Glycobiology 10:90
78. Makkee M, Kieboom A, Bekkum H, Roels J (1980) Chem Commun 930
79. Pamies O, Bäckvall J (2003) Chem Rev 103:3247
80. Pamies O, Bäckvall J (2001) Adv Synth Catal 343:726
81. Rouhi A (2002) Chem Eng News 43
82. Steckhan E (1994) Top Curr Chem 170:83
83. Schmid A, Hollmann F, Bühler B (2002) In: Drauz K, Waldmann H (eds) Enzyme catalysis in organic synthesis, vol 3, 2nd edn. VCH-Wiley, p 1108
84. Steckhan E, Arns T, Heineman WR, Hilt G, Hoormann D, Jörissen J, Kröner L, Lewall B, Pütter H (2001) Chemosphere 43:63
85. Genders JD, Pletcher D (1996) Chem Ind-London 682
86. Wong C-H, Whitesides GM (1994) Enzymes in synthetic organic chemistry. Elsevier Science, Oxford
87. Hollmann F, Schmid A, Steckhan E (2001) Angew Chem Int Edit 40:169
88. Hollmann F, Witholt B, Schmid A (2002) J Mol Catal B-Enzym 19:167
89. Frede M, Steckhan E (1991) Tetrahedron Lett 32:5063
90. Brielbeck B, Frede M, Steckhan E (1994) Biocatalysis 10:49
91. Ruppert R, Herrmann S, Steckhan E (1987) Tetrahedron Lett 28:6583
92. Westerhausen D, Herrmann S, Hummel W, Steckhan E (1992) Angew Chem Int Edit 31:1529
93. Steckhan E, Herrmann S, Ruppert R, Dietz E, Frede M, Spika E (1991) Organometallics 10:1568
94. Schmid A, Hofstetter K, Feiten HJ, Hollmann F, Witholt B (2001) Adv Synth Catal 343:732
95. Delecouls-Servat K, Basseguy R, Bergel A (2002) Bioelectrochemistry 55:93
96. Hilt G, Steckhan E (1993) J Chem Soc Chem Commun 1706
97. Hilt G, Jarbawi T, Heineman WR, Steckhan E (1997) Chem-Eur J 3:79
98. Hilt G, Lewall B, Montero G, Utley JHP, Steckhan E (1997) Liebigs Ann-Recl: 2289
99. Schroeder I, Steckhan E, Liese A (2003) J Electroanal Chem 541:109
100. Degenring D, Schröder I, Liese A, Greiner L (2004) Org Process Res Dev (in press)
101. van de Velde F, van Rantwijk F, Sheldon RA (2001) Trend Biotechnol 19:73
102. Adam W (1999) Adv Biochem Eng/Biotechnol 63:73
103. Colonna S, Gaggero N, Richelmi C, Pasta P (1999) Trend Biotechnol 17:163
104. van Deurzen MPJ, van Rantwijk F, Sheldon RA (1997) Tetrahedron 53:13183
105. Allain EJ, Hager LP, Deng L, Jacobsen EN (1993) J Am Chem Soc 115:4415
106. Dexter AF, Lakner FJ, Campbell RA, Hager LP (1995) J Am Chem Soc 117:6412
107. Lakner FJ, Hager LP (1996) J Org Chem 61:3923
108. Seelbach K, Dreuzen MPJv, Rantwijk Fv, Sheldon RA, Kragl U (1997) Biotechnol Bioeng 55:283
109. Seelbach K (1997) Chloroperoxidase-Ein industrieller Katalysator? Regio- und enantioselektive Oxidationen. PhD Thesis, Rheinische Friedrich-Wilhelms- Universität, Bonn
110. Okrasa K, Guibé-Jampel E, Therisod M (2000) J Chem Soc Perk T 1:1077
111. van de Velde F, Lourenco ND, Bakker M, van Rantwijk F, Sheldon RA (2000) Biotechnol Bioeng 69:286
112. Laane C, Weyland A, Franssen M (1986) Enzyme Microb Tech 8:345
113. Biade A-E, Bourdillon C, Laval J-M, Mairesse G, Moiroux J (1992) J Am Chem Soc 114:893
114. Butt JN, Filipiak M, Hagen WR (1997) Eur J Biochem 245:116
115. Gros P, Zaborosch C, Schlegel HG, Bergel A (1996) J Electroanal Chem 405:189
116. Smith ET, Odom LD, Awramko JA, M.Chiong, Blamey J (2001) J Biol Inorg Chem 6:227
117. Morozov SV, Karyakina EE, Zorin NA, Varfolomeyev SD, Cosnier S, Karyakin AA (2002) Bioelectrochemistry 55:169
118. Delecouls K, Saint-Aguet P, Zaborosch C, Bergel A (1999) J Electroanal Chem 468:139
119. Delecouls K, Basseguy R, Bergel A (1998) Actual Chimique 91
120. Bergel A, DevauxBasseguy R (1996) J Chim Phys PCB 93:753
121. Jandel L, Schulte B, Bückmann AF, Wandrey C (1980) J Membrane Sci 7:185
122. Flaschel E (1983) Adv Biochem Eng/Biotechnol 26:73
123. Kula M-R, Wandrey C (1987) Method Enzymol 136:9
124. Buchholz K, Kasche V (1997) Biokatalysatoren und Enzymtechnologie. VCH Verlags-gesellschaft mbH, Weinheim
125. Bayer E, Schurig V (1975) Angew Chem 87:484
126. Bayer E, Gatfield I, Mutter H, Mutter M (1978) Tetrahedron 34:1829
127. Kragl U, Dreisbach C (1996) Angew Chem 108:684
128. Felder M, Giffels G, Wandrey C (1997) Tetrahedron Asymmetr 8:1975
129. Giffels G, Beliczey J, Felder M, Kragl U (1998) Tetrahedron Asymmetr 9:691
130. Wöltinger J, Bommarius AS, Drautz K, Wandrey C (2001) Org Process Res Dev 5:241
131. Wöltinger J, Drauz K, Bommarius AS (2001) Appl Catal A-Gen 221:171
132. Tsogoeva SB, Woltinger J, Jost C, Reichert D, Kuhnle A, Krimmer HP, Drauz K (2002) Synlett 707
133. Wöltinger J, Henniges H, Krimmer H-P, Bommarius AS, Drauz K (2001) Tetrahedron Asymmetr 12:2095
134. Laue S, Greiner L, Wöltinger J, Liese A (2001) Adv Synth Catal 343:711
135. Kragl U, Dreisbach C, Wandrey C (1996) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds, vol 2. VCH, Weinheim, p 832
136. Rissom S, Beliczey J, Giffels G, Kragl U, Wandrey C (1999) Tetrahedron Asymmetr 10:923
137. Kragl U, Dwars T (2001) Trend Biotechnol 19:442
138. Bergbreiter DE (2002) Chem Rev 102:3345
139. Bayer E, Schurig V (1975) Angew Chem 87:484
140. Steckhan E, Herrmann S, Ruppert R, Thömmes J, Wandrey C (1990) Angew Chem 102:445
141. Leadbeater NE, Marco M (2002) Chem Rev 102:3217
142. Köllner C, Pugin B, Togni A (1998) J Am Chem Soc 120:10274
143. Brinkmann N, Giebel D, Lohmer G, Reetz MT, Kragl U (1999) J Catal 183:163
144. Hovestad NJ, Eggeling EB, Heidbüchel HJ, Jastrzebski JTBH, Kragl U, Keim W, Vogt D, van Koten G (1999) Angew Chem 111:1763
145. Sablong R, Schlotterbeck U, Vogt D, Mecking S (2003) Adv Synth Catal 345:333
146. Smet K, Aerts S, Ceulemans E, Vankelecom I, Jacobs P (2001) Chem Commun 7:597
147. De Smet K, Pleysier A, Vankelecom IFJ, Jacobs PA (2003) Chem-Eur J 9:334
148. Wandrey C, Flaschel E (1978) Chem Ing Tech 50:231
149. Wandrey C, Flaschel E (1979) Adv Biochem Eng 12:147
150. Wandrey C, Flaschel E, Schuegerl K (1977) Chem Ing Tech 49:257
151. Fodor K (1999) Enantiomer 4:497
152. De Vos WE, Vankelecom IJF, Jacobs P (2000) Chiral catalyst immobilization and recycling. Wiley-VCH, Weinheim
153. Blaser H-U (1991) Tetrahedron Asymmetr 2:843
154. Cornils B, Herrmann WA (2000) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds. Wiley-VCH, New York, p 575
155. Sym EA (1936) Biochem J 30:609
156. Kvittengen L, Hailing PJ (1999) Trends Biotechnol 17:343
157. Klibanov A (2001) Nature 409:241
158. Griengl H, Kiempier N, Pöchlauer P, Schmidt M, Shi N, Mackova A (1998) Tetrahedron 54:14477
159. Bauer M, Griengl H, Steiner W (1999) Enzyme Microb Tech 24:514
160. Villela-Filho M, Wolberg M, Muller M, Hummel W, Liese A, Wandrey C (2002) Chem Ing Tech 74:657
161. Villela Filho M, Stillger T, Mueller M, Liese A, Wandrey C (2003) Angew Chem Int Edit 42:2993
162. Rosche B, Sandford V, Breuer M, Hauer B, Rogers PL (2002) J Mol Catal B-Enzym 19:109
163. Rosche B, Leksawasdi N, Sandford V, Breuer M, Hauer B, Rogers P (2002) Appl Microb Biot 60:94
164. Gröger H, Hummel W, Rollmann C, Chamouleau F, Hüsken H, Werner H, Wunderlich C, Abokitse K, Drauz K, Buchholz S (2004) Tetrahedron 60:633
165. Schöfer SH, Kaftzik N, Wasserscheid P, Kragl U (2001) Chem Commun 425-426
166. Park S, Kazlauskas R (2001) J Org Chem 66:8395
167. Reetz M, Wiesenhöfer W, Francio G, Leitner W (2002) Chem Commun 992
168. Sun Y, Wang J, LeBlond C, Landau RN, Laquidara J, Sowa JR, Blackmond DG (1997) J Mol Catal B-Enzym 115:495
169. Sun Y (1996) J Am Chem Soc 118:1348
170. Bommarius A, Krimmer H-P, Reichert D, Almena J, Karau A, Wöltinger J, Drauz K, Liese A, Greiner L, Wandrey C (2001) Volumenbegasung DE 101 63 168.5 (21.12.2001, German patent application)
171. Greiner L, Mueller DH, van den Ban ECD, Woeltinger J, Wandrey C, Liese A (2003) Adv Synth Catal 345:679
172. Noll T, Biselli M, Wandrey C (1996) BIOSpektrum 1:65
173. Rissom S, Schwarz-Linek U, Vogel M, Tishkov V, Kragl U (1997) Tetrahedron Asymmetr 8:2523
174. Bongs J, Hahn D, Schörken U, Sprenger GA, Kragl U, Wandrey C (1997) Biotechnology Lett 19:213
175. Schwab GM, Rudolph LM (1932) Naturwissenschaften 20:362
176. Lipkin D, Stewart TD (1939) J Am Chem Soc 61:3295
177. Nozaki H, Moriuti S, Takaya H, Noyori R (1966) Tetrahedron Lett 5239
178. Knowles WS, Sabacky MJ (1968) Chem Commun 1445
179. Horner L, Siegel H, Büthe H (1968) Angew Chem 80:1034
180. Izumi Y (1971) Angew Chem 83:956
181. Knowles WS (1983) Ace Chem Res 16:106
182. Katsuki T, Sharpless KB (1980) J Am Chem Soc 102:5974
183. Itsuno S, Nakano M, Ito K, Hirao A, Owa M, Kanda N, Nakahama S (1985) J Chem Soc Perk T 1 I:2615
184. Corey EJ, Bakshi RK, Shibata S (1987) J Am Chem Soc 109:5551
185. Oguni N, Omi T (1984) Tetrahedron Lett 25:2823
186. Jacobsen EN, Marko I, Mungal WS, Schröder G, Sharpless KB (1988) J Am Chem Soc 110:1968
187. Jacobsen EN, Zhang W, Muci AR, Ecker JR, Deng L (1991) J Am Chem Soc 113:7063
188. Wan K, Davis ME (1983) Tetrahedron Asymmetr 4:2461
189. Noyori R, Hashigushi S (1996) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds. VCH, New York, p 575
190. Folienserie (1985) Folienserie des Fonds der Chemischen Industrie, vol 20. See http://www.biologe.de/Nuetzliches/FCI-CD/
191. Frost & Sullivan (2003) Analysis of developments in global chiral technology markets (Report B105). Frost & Sullivan, San Antonio, TX
192. Liese A, Lütz S (2002) GDCh Monographie der GDCh-Fachgruppe Angewandte Elektrochemie (Elektronentransfer in Chemie und Biochemie). GDCh-Monographie, Frankfurt 23:305