Enzymes, 5. Enzymes in Organic Synthesis
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Enzymes
Wolfgang Aehle, Richard N. Perham, Gerhard Michal, Albert Jonke, Gopal K. Chotani, Timothy C. Dodge, Andreas Herman Terwisscha van Scheltinga, Christian Gölker, Meng H. Heng, John Kan, Todd Becker, Saburo Fukui, Atsuo Tanaka, Hans de Nobel, Brian Jones, Rick Bott, Charlotte Horsmans Poulsen, Karsten M. Kragh, Jens Frisback Sorensen, Catherine Grassin, Marga Herweijer, Jan Wilms, André de Roos, Jorn Borch Soe, Ivan Herbots, Beatrix Kottwitz, Peter J. Reilly, Richard L. Antrim, Heidi Burrows, Herman B. M. Lenting, Liisa Viikari, Anna Suurnäkki, Marja-Leena Niku-Paavola, Johanna Buchert, Karl-Heinz Maurer, Andrea Saettler, Herbert Waldmann, Carsten Schultz, Harald Gröger, Carlo Dinkel, Karlheinz Drauz, Georg-Burkhard Kresse, Rainer Schmuck, Karl Wulff, Günther Henniger, Christoph Kessler, Alice J. Caddow, Beth Concoby,
Enzymes
Richard N. Perham, Gerhard Michal, Albert Jonke, Andreas Herman Terwisscha van Scheltinga, Christian Gölker, Saburo Fukui, Atsuo Tanaka, Helmut Uhlig, Walter E. Goldstein, Hans A. Hagen, Sven Pedersen, Bob Poldermans, Ernst H. Reimerdes, Wolfgang Leuchtenberger, Ulf Plöcker, Herbert Waldmann, George A. Whitesides, Georg-Burkhard Kresse, Karl Wulff, Günther Henniger, Leopold Flohé, Wolfgang A. Günzler, Christoph Kessler, Knud Aunstrup,
Wolfgang Aehle,
Herbert Waldmann,
Carsten Schultz, Harald Gröger, Carlo Dinkel, Karlheinz Drauz,
Wolfgang Aehle
Genencor International B. V., Leiden, The Netherlands
Search for more papers by this authorHerbert Waldmann
Max-Planck-Institut für molekulare Physiologie, Dortmund, Germany
Search for more papers by this authorWolfgang Aehle,
Herbert Waldmann,
Carsten Schultz, Harald Gröger, Carlo Dinkel, Karlheinz Drauz,
Wolfgang Aehle
Genencor International B. V., Leiden, The Netherlands
Search for more papers by this authorHerbert Waldmann
Max-Planck-Institut für molekulare Physiologie, Dortmund, Germany
Search for more papers by this authorAbstract
The article contains sections titled:
1. |
Introduction |
2. |
Examples of Enzymatic Conversions |
3. |
Enzyme-Analogous Catalysts |
4. |
Commercial Applications |
5. |
Outlook |
References
- 1 K. Drauz, H. Waldmann, eds., Enzyme Catalysis in Organic Synthesis, VCH, Weinheim, Germany, 1995.
- 2
C.-H. Wong,
G. W. Whitesides,
Enzymes in Synthetic Organic Chemistry,
Elsevier,
Oxford,
1994
10.1016/B978-0-08-035941-0.50005-7 Google Scholar
- 3 W. D. Fessner (ed.): Biocatalysis–From Discovery to Application, Springer, Berlin, 1999.
- 4 C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 107 (1995) 453; Angew. Chem., Int. Ed. Engl. 34 (1995) 521.
- 5 C. Walsh, Nature 409 (2001) 226.
- 6 K. M. Koeller, C.-H. Wong, Nature 409 (2001) 232.
- 7 C. Khosla, P. B. Harbury, Nature 409 (2001) 247.
- 8 F. H. Arnold, Nature 409 (2001) 253.
- 9 A. Schmid, J. S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, B. Witholt, Nature 409 (2001) 258.
- 10 A. M. Klibanov, Nature 409 (2001) 241.
- 11 S. M. Roberts, Biocatalysis for Fine Chemicals Synthesis, Wiley-VCH, Weinheim, Germany, 1999.
- 12
K. Faber,
Biotransformations in Organic Chemistry,
4th edition,
Springer,
Berlin,
2000.
10.1007/978-3-642-98071-8 Google Scholar
- 13 W. Gerhartz, Enzymes in Industry, VCH, Weinheim, Germany, 1990.
- 14 A. Zaks, D. R. Dodds, Curr. Opin. Drug Discov. Dev. 1 (1998) 290.
- 15 K. Mori, Synlett (1995) 1097.
- 16 J.-M. Fang, C.-H. Lin, C. W. Bradshaw, C.-H. Wong, J. Chem. Soc. Perkin Trans. 1 (1995) 967.
- 17 J.-M. Fang, C.-H. Wong, Synlett (1994) 393.
- 18 H. Waldmann, D. Sebastian, Chem. Rev. (1994) 911.
- 19 T. Pathak, H. Waldmann, Curr. Opin. Chem. Biol. 2 (1998) 112.
- 20
R. D. Schmid,
R. Verger,
Angew. Chem.
110
(1998)
1694;
10.1002/(SICI)1521-3757(19980619)110:12<1694::AID-ANGE1694>3.0.CO;2-3 Web of Science® Google ScholarAngew. Chem., Int. Ed. Engl. 1998, 37, 1608.10.1002/(SICI)1521-3773(19980703)37:12<1608::AID-ANIE1608>3.0.CO;2-V CAS Web of Science® Google Scholar
- 21 D. G. Drueckhammer, W. J. Hennen, R. L. Pederson, C. F. Barbas III, C. M. Gautheron, T. Krach, C.-H. Wong, Synthesis (1991) 499.
- 22 A. L. Margolin, Enzyme Microb. Technol. 15 (1993) 266.
- 23
M. T. Reetz,
Angew. Chem.
2001,
113,
292;
10.1002/1521-3757(20010119)113:2<292::AID-ANGE292>3.0.CO;2-F Google ScholarAngew. Chem., Int. Ed. Engl. 40 (2001) 284.10.1002/1521-3773(20010119)40:2<284::AID-ANIE284>3.0.CO;2-N CAS PubMed Web of Science® Google Scholar
- 24 H. Joo, Z. Lin, F. H. Arnold, Nature (1999) 399, 670.
- 25
G. Carrea,
S. Riva,
Angew. Chem.
112
(2000)
2312;
10.1002/1521-3757(20000703)112:13<2312::AID-ANGE2312>3.0.CO;2-4 Google ScholarAngew. Chem., Int. Ed. Engl. 39 (2000) 2226.10.1002/1521-3773(20000703)39:13<2226::AID-ANIE2226>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 26 U. T. Bornscheuer, R. J. Kazlauskas, Wiley, Weinheim, 1999.
- 27 A. M. P. Koshinen, A. M. Klibanov (eds.): Enzymatic Reactions in Organic Media, Chapman & Hall, Glasgow, 1991.
- 28 M. Therisod, A. M. Klibanov, J. Am. Chem. Soc. 108 (1986) 5638.
- 29 S. Riva, J. Chopineau, A. P. G. Kieboom, A. M. Klibanov, J. Am. Chem. Soc. 110 (1988) 584.
- 30 S. Riva, R. Bovara, G. Ottolina, F. Secundo, G. Carrea, J. Org. Chem. 54 (1989) 3161.
- 31 G. Ottolina, G. Carrea, S. Riva, Biocatalysis 5 (1991) 131.
- 32 D. L. Delinck, A. L. Margolin, Tetrahedron Lett. 31 (1990) 3093.
- 33 B. Danieli, G. Lesma, M. Luisetti, S. Riva, Tetrahedron 53 (1997) 5855.
- 34 Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 65 (2000) 83.
- 35 M. Schudok, G. Kretzschmar, Tetrahedron Lett. 38 (1997) 387.
- 36 G. Kirchner, M. P. Scollar, A. M. Klibanov, J. Am. Chem. Soc. 107 (1985) 7072.
- 37 A. Ghogare, G. S. Kumar, J. Chem. Soc, Chem. Commun. 1990, 134.
- 38 R. V. Nair, M. M. Salunkhe, Synth. Commun. 30 (2000) 134.
- 39 P.-J. Ulm, D. G. Drueckhammer, J. Am. Chem. Soc. 120 (1998) 5605.
- 40
C. Dinkel,
M. Moody,
A. E.. Traynor-Kaplan,
C. Schultz,
Angew. Chem.
113
(2001)
3093;
10.1002/1521-3757(20010817)113:16<3093::AID-ANGE3093>3.0.CO;2-A Google ScholarAngew. Chem., Int. Ed. Engl. 40 (2001) 3004.10.1002/1521-3773(20010817)40:16<3004::AID-ANIE3004>3.0.CO;2-O CAS PubMed Web of Science® Google Scholar
- 41 M. T. Reetz, K. Schimossek, Chimia 50 (1996) 668.
- 42 G. M. Ramos-Tombo, H.-P. Shar, I. Fernandes, X. Busquets, O. Ghisalba, Tetrahedron Lett. 27 (1986) 5707.
- 43 T. Sugahara, K. Ogasawara, Synlett (1996) 319.
- 44 M. T. Reetz, Adv. Mater. 9 (1997) 943.
- 45
M. T. Reetz,
A. Zonta,
J. Simpelkamp,
Angew. Chem.
107
(1995)
373;
10.1002/ange.19951070325 Google ScholarAngew. Chem., Int. Ed. Engl. 34 (1995) 301.
- 46
M. T. Reetz,
A. Zonta,
J. Simpelkamp,
Biotechnol. Bioeng.
49
(1996)
527.
10.1002/(SICI)1097-0290(19960305)49:5<527::AID-BIT5>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 47 M. T. Reetz, R. Wenkel, D. Avenir, Synthesis (2000) 781.
- 48 V. M. Balcao, H. Akita, Biocatal. Biotransform. 13 (1996) 141;
- 49 A. L. Paiva, F. X. Malcata, Enzyme Microb. Technol. 18 (1996) 392.
- 50 A. L. Margolin, Trends Biotechnol. 14 (1996) 223.
- 51
T. Zelinski,
H. Waldmann,
Angew. Chem.
109
(1997)
746;
10.1002/ange.19971090709 Google ScholarAngew. Chem., Int. Ed. Engl. 36 (1997) 722.
- 52
N. St. Clair,
Y.-F. Wang,
A. L. Margolin,
Angew. Chem.
112
(2000)
388;
10.1002/(SICI)1521-3757(20000117)112:2<388::AID-ANGE388>3.0.CO;2-W Google ScholarAngew. Chem., Int. Ed. Engl. 39 (2000) 380.10.1002/(SICI)1521-3773(20000117)39:2<380::AID-ANIE380>3.0.CO;2-1 CAS PubMed Web of Science® Google Scholar
- 53 A. Bommarius, M. Kottenham, H. Klenk, K. Drauz, in: Microbial Reagents in Organic Synthesis, S. Servi (ed.): Kluwer Academic Publishers, Dordrecht, 1992, p. 161.
- 54 K. Drauz, M. Kottenham, K. Makryaleas, H. Klenk, M. Bernd, Angew. Chem. 103 (1991) 704; Angew. Chem., Int. Ed. Engl. 30 (1991) 712.
- 55 M. Beller, M. Eckert, H. Geissler, B. Napierski, H.-P. Rebenstock, E. W. Holla, Chem. Eur. J. 4 (1998) 935.
- 56 P. Hönicke-Schmidt, M. P. Schneider, J. Chem. Soc., Chem. Commun. (1990) 648.
- 57 A. de Raadt, N. Kempier, K. Faber, H. Griengl, J. Chem. Soc., Perkin Trans. 1 (1992) 137.
- 58 M. Kobayashi, N. Yanaka, T. Nagasawa, H. Yamada, Tetrahedron 46 (1990) 5587.
- 59 R. Bauer, H.-J. Knackmuss, A. Stolz, Appl. Microbiol. Biotechnol. 49 (1998) 89.
- 60 D. R. Dodds, J. B. Jones, J. Am. Chem. Soc. 110 (1988) 577.
- 61
M. Wolberg,
W. Hummel,
C. Wandrey,
M. Müller,
Angew. Chem.
112
(2000)
4476;
10.1002/1521-3757(20001201)112:23<4476::AID-ANGE4476>3.0.CO;2-C Google ScholarAngew. Chem., Int. Ed. Engl. 39 (2000) 4306
- 62 B. L. Hirschbein, G. M. Whitesides, J. Am. Chem. Soc. 104 (1982) 4458.
- 63 C. W. Bradshaw, C.-H. Wong, W. Hummel, M.-R. Kula, Bioorg. Chem. 19 (1991) 29.
- 64 M.-J. Kim, J. Y. Kim, J. Chem. Soc., Chem. Commun. (1991) 326.
- 65 Z. Shaked, G. M. Whitesides, J. Am. Chem. Soc. 102 (1980) 7104.
- 66 C. Wandrey, A. F. Bückmann, M.-R. Kula, Biotechnol. Bioeng. 23 (1981) 1789.
- 67 C. W. Bradshaw, H. Fu, G.-J. Shen, C.-H. Wong, J. Org. Chem. 57 (1992) 1526.
- 68 G.-J. Shen, Y.-F. Wang, C.-H. Wong, J. Chem. Soc., Chem. Commun. (1990) 677.
- 69 Y. Naoshima, H. Hasegawa, T. Nishiyama, A. Nakamura, Bull. Chem. Soc. Jpn. 62 (1989) 608.
- 70 K. Mori, H. Mori, Org. Synth. 68 (1989) 56.
- 71 K. Mori, Bull. Soc. Chim. Belg. 1992, 101, 393.
- 72 M. Desrut, A. Kergomard, M. F. Renard, H. Veschambre, Tetrahedron 37 (1981) 3825.
- 73 A. Kergomard, M. F. Renard, H. Veschambre, J. Org. Chem. 47 (1982) 792.
- 74 P. Ferraboschi, S. Casati, E. Santaniello, Tetrahedron Asymm. 5 (1991) 19.
- 75 N. S. Y. Ng, L.-C. Yuan, I. J. Jakovac, J. B. Jones, Tetrahedron 40 (1984) 1235.
- 76 I. J. Jakovac, H. B. Goodbrand, K. P. Lok, J. B. Jones, J. Am. Chem. Soc. 104 (1982) 4659.
- 77 J. Lehmann, A. Moritz, Liebigs Ann. Chem. (1991) 937.
- 78 S. V. Ley, F. Sternfeld, Tetrahedron 45 (1989) 3463.
- 79 M. E. De Luca, T. Hudlicky, Tetrahedron Lett. 31 (1990) 13.
- 80 D. R. Boyd, N. D. Sharma, R. Boyle, B. T. McMurray, T. A. Evans, J. F. Malone, H. Dalton, J. Chima, G. N. Sheldrake, J. Chem. Soc., Chem. Commun. (1993) 49.
- 81 T. Hudlicky, in: Microbial Reagents in Organic Synthesis, S. Servi ed., Kluwer Academic Publishers, Dordrecht, 1992, p. 123.
- 82 T. Hudlicky, H. Luna, J. D. Price, F. Rulin, Tetrahedron Lett. 30 (1989) 4053.
- 83 S. M. Roberts, P. W. H. Wan, J. Mol. Catal. B: Enzymat. 4 (1998) 111.
- 84 S. Rissom, U. Schwarz-Linek, M. Vogel, V. I. Tishkov, U. Kragl, Tetrahedron Asymm. 8 (1997) 2523.
- 85 A. Archelas, R. Furstoss, in W. D. Fessner (ed.): Biocatalysis–From Discovery to Application, pp. 159–191, Springer, Berlin, 1999.
- 86 W.-D. Woggon, Topics in Current Chemistry, 184 (1996) 40.
- 87 E. J. Allain, L. P. Hager, L. Deng, E. J. Jacobsen, J. Am. Chem. Soc. 115 (1993) 4415.
- 88 W.-D. Fessner, Kontakte (Darmstadt) 1993 no. 1, 23.
- 89 W.-D. Fessner, Curr. Opin. Chem. Biol. 2 (1998) 85.
- 90 G. Guanti, L. Banfi, M. T. Zannetti, Tetrahedron Lett. 41 (2000) 3181.
- 91 H.-L. Arth, W.-D. Fessner, Carbohydr. Res. 305 (1998) 313.
- 92 F. Morís-Varas, X.-H. Qian, C.-H. Wong, J. Am. Chem. Soc. 118 (1996) 7647.
- 93 C.-C. Lin, F. Morís-Varas, G. Weitz-Schmidt, C.-H. Wong, Bioorg. Med. Chem. 7 (1999) 425.
- 94 W.-D. Fessner, G. Sinerius, A. Schneider, M. Dreyer, G. E. Schulz, J. Badia, J. Aguilar, Angew. Chem. 103 (1991) 596; Angew. Chem., Int. Ed. Engl. 30 (1991) 555.
- 95 W.-D. Fessner, C. Walter, Topics in Current Chemistry 184 (1996) 97.
- 96 R. Schoevaart, F. van Rantwijk, R. A. Sheldon, Biotechnol. Bioeng. 70 (2000) 349.
- 97 R. Schoevaart, F. van Rantwijk, R. A. Sheldon, J. Org. Chem. 65 (2000) 6940.
- 98 H. Oikawa, T. Kobayashi, K. Katayama, Y. Suzuki, A. Ichihara, J. Org. Chem. 63 (1998) 8748.
- 99 K. M. Koeller, C.-H. Wong, Chem. Rev. 100 (2000) 4465.
- 100 H. Herzner, T. Reipen, M. Schultz, H. Kunz, Chem. Rev. 100 (2000) 4495.
- 101
O. Seitz,
ChemBioChem
1
(2000)
214.
10.1002/1439-7633(20001117)1:4<214::AID-CBIC214>3.0.CO;2-B CAS PubMed Web of Science® Google Scholar
- 102
P. M. St. Hilaire,
M. Meldal,
Angew. Chem.
112
(2000)
1210;
10.1002/(SICI)1521-3757(20000403)112:7<1210::AID-ANGE1210>3.0.CO;2-7 Google ScholarAngew. Chem., Int. Ed. Engl. 39 (2000) 1162.10.1002/(SICI)1521-3773(20000403)39:7<1162::AID-ANIE1162>3.0.CO;2-6 PubMed Web of Science® Google Scholar
- 103
B. G. Davis,
J. Chem. Soc. Perkin Trans.
1
(1999)
3215.
10.1039/a809773i Google Scholar
- 104 S. C. T. Svensson, J. Thiem, Carbohydr. Res. 200 (1990) 39.
- 105 J. Thiem, B. Sauerbrei, Angew. Chem. 103 (1991) 1521; Angew. Chem., Int. Ed. Engl. 30 (1991) 1503.
- 106 T. Usui, S. Kubota, H. Ohi, Y. Ishido, Glycoconjug. J. 8 (1991) 272.
- 107 G. F. Herrmann, Y. Ichikawa, C. Wandrey, F. C. A. Gaeta, J. C. Paulson, C.-H. Wong Tetrahedron Lett. 34 (1993) 3091.
- 108 C. Augé, R. Fernandez-Fernandez, C. Gautheron, Carbohydr. Res. 200 (1990) 257.
- 109 Y. Ichikawa, R. Wang, C.-H. Wong, Methods Enzymol. 230 (1994) 300.
- 110 T. Bülter, L. Elling, Glycoconjug. J. 16 (1999) 147.
- 111 K. Witte, P. Sears, R. Martin, C.-H. Wong, J. Am. Chem. Soc. 119 (1997) 2114.
- 112 K. Takegawa, M. Tabuchi, S. Yamaguchi, A. Kondo, I. Kato, S. Iwahara, J. Biol. Chem. 270 (1995) 3094.
- 113
M. Schelhaas,
S. Glomsda,
M. Hänsler,
W. Vogt,
H.-D. Jakubke,
H. Waldmann,
Angew. Chem.
108
(1996)
82;
10.1002/ange.19961080114 Google ScholarAngew. Chem. Int. Ed. Engl. 35 (1996) 106.
- 114
H. Waldmann,
E. Nägele,
Angew. Chem.
107
(1995)
2425;
10.1002/ange.19951072014 Google ScholarAngew. Chem. Int. Ed. Engl. 34 (1995) 2259.
- 115
T. Pohl,
H. Waldmann,
Angew. Chem.
108
(1996)
1829;
10.1002/ange.19961081531 Google ScholarAngew. Chem. Int. Ed. Engl. 35 (1996) 1720.
- 116 T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702.
- 117
F. Eisele,
H. Waldmann,
Angew. Chem.
113
(2001)
382;
10.1002/1521-3757(20010119)113:2<382::AID-ANGE382>3.0.CO;2-F Google ScholarAngew. Chem., Int. Ed. Engl. 40 (2001) 369.10.1002/1521-3773(20010119)40:2<369::AID-ANIE369>3.0.CO;2-7 CAS PubMed Web of Science® Google Scholar
- 118
R. Machauer,
H. Waldmann,
Angew. Chem.
112
(2000)
1503;
10.1002/(SICI)1521-3757(20000417)112:8<1503::AID-ANGE1503>3.0.CO;2-2 Google ScholarAngew. Chem. Int. Ed. Engl. 39 (2000) 1449.10.1002/(SICI)1521-3773(20000417)39:8<1449::AID-ANIE1449>3.0.CO;2-A CAS PubMed Web of Science® Google Scholar
- 119 T. Kappes, H. Waldmann, Carbohydr. Res. 305 (1998) 341.
- 120 P. G. Schultz, R. A. Lerner, Science 269 (1995) 1835.
- 121 J. Hasserodt, Synlett (1999) 2007.
- 122 D. Hilvert, Annu. Rev. Biochem. 69 (2000) 751
- 123 S. C. Sinha, C. F. Barbas III, R. A. Lerner, Proc. Natl. Acad. Sci. USA 95 (1998) 14603.
- 124
G. Z. Zhong,
D. Shabat,
B. List,
J. Anderson,
S. C. Sinha,
R. A. Lerner,
C. F. Barbas III,
Angew. Chem.
110
(1998)
2609;
10.1002/(SICI)1521-3757(19980918)110:18<2609::AID-ANGE2609>3.0.CO;2-E Web of Science® Google ScholarAngew. Chem., Int. Ed. Engl. 37 (1998) 2481.10.1002/(SICI)1521-3773(19981002)37:18<2481::AID-ANIE2481>3.0.CO;2-T CAS Web of Science® Google Scholar
- 125 K. D. Janda, C. G. Shevlin; R. A. Lerner, Science, 259 (1993) 490.
- 126 K. D. Janda, C. G. Shevlin; R. A. Lerner, J. Am. Chem. Soc. 117 (1995) 2659.
- 127 K. Gruber, B. Zhou, K. N. Houk, R. A. Lerner, C. G. Shevlin, I. A. Wilson, Biochemistry, 38 (1999) 7062
- 128 V. E. Gouverneur, K. N. Houk, B. de Pascual-Teresa, B. Beno, K. D. Janda, R. A. Lerner, Science, 262 (1993) 204.
- 129 G. Zhong, T. Hoffmann, R. A. Lerner, S. Danishefsky, C. F. Barbas III, J. Am. Chem. Soc. 119 (1997) 8131.
- 130
B. Seelig,
S. Keiper,
F. Stuhlmann,
A. Jäschke,
Angew. Chem.
112
(2000)
4764;
10.1002/1521-3757(20001215)112:24<4764::AID-ANGE4764>3.0.CO;2-V Google ScholarAngew. Chem. Int. Ed. Engl. 39 (2000) 4576.10.1002/1521-3773(20001215)39:24<4576::AID-ANIE4576>3.0.CO;2-J CAS PubMed Web of Science® Google Scholar
- 131
C. Frauendorf,
A. Jäschke,
Angew. Chem.
110,
(1998)
1449;
10.1002/(SICI)1521-3757(19980518)110:10<1449::AID-ANGE1449>3.0.CO;2-3 Google ScholarAngew. Chem. Int. Ed. Engl. 37 (1998) 1378.10.1002/(SICI)1521-3773(19980605)37:10<1378::AID-ANIE1378>3.0.CO;2-# CAS Web of Science® Google Scholar
- 132 G. F. Joyce, Proc. Natl. Acad. Sci. USA 95 (1998) 5845.
- 133
H. Gröger,
J. Wilken,
Angew. Chem.
113
(2001)
545;
10.1002/1521-3757(20010202)113:3<545::AID-ANGE545>3.0.CO;2-J Google ScholarAngew. Chem. Int. Ed. Engl. 40 (2001) 529.10.1002/1521-3773(20010202)40:3<529::AID-ANIE529>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 134 B. List, P. Pojarliev, C. Castello, Org. Lett. 3 (2001) 573.
- 135 W. Notz, B. List, J. Am. Chem. Soc. 122 (2000) 7386.
- 136 T. Bui, C. F. Barbas III, Tetrahedron Lett. 41 (2000) 6951.
- 137 B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 122 (2000) 2395.
- 138 J. W. Trauger, R. M. Kohli, H. D. Mootz, M. A. Marahiel, C. T. Walsh, Nature 407, (2000) 215.
- 139 V. Cerovský, J. Kockskämper, H. G. Glitsch, F. Bordusa, ChemBioChem 2 (2000) 126.
- 140 Chemical Economics Handbook, SRI International, 1991.
- 141 T. Nagasawa, H. Yamada, Tibtech 7 (1989) 153.
- 142 Y. Asano, T. Yasuda, Y. Tani, H. Yamada, Agric. Biol. Chem. 46 (1982) 1183.
- 143 I. Watanabe, Y. Satoh, K. Enomoto, S. Seki, K. Sakashita, Agric. Biol. Chem. 51 (1987) 3201.
- 144 M. Kobayashi, T. Nagasawa, H. Yamada, Tibtech 10 (1992) 402.
- 145 C. Chassin, Chimica Oggi–Chemistry Today 17 (1999 nos. 5/6, 48.
- 146 An overview about this reaction is given in: A. S. Bommarius, M. Schwarm, K. Drauz, Chimia 55 (2001) 50.
- 147 Ref. (1), pp. 963–975.
- 148 J. A. Jongejau, J. B. A. van Tol, J. A. Duine, Chem. Today (1994) 15.
- 149 J. P. Rasor, Speciality Chemicals 1995, S5.
- 150 T. Tosa, T. Mori, N. Fuse, I. Chibata, Agric. Biol. Chem. 1969, 1047.
- 151 I. Chibata, T. Tosa, T. Sato, T. Mori, Methods Enzymol. (1976) 746.
- 152 C. Wandrey, E. Flaschel, Adv. Biochem. Eng. (1979) 147.
- 153 Degussa/GBF, C. Wandrey, R. Wichmann, W. Leuchtenberger, M. R. Kula, US 4.304.858 (1981).
- 154 W. Leuchtenberger, M. Karrenbauer, U. Plöcker, Enzyme Eng. 7 Ann. N. Y. Acad. Sci. (1984) 434.
- 155 A. S. Bommarius, K. Drauz, H. Klenk, C. Wandrey, Enzyme Eng. 11 Ann. N. Y. Acad Sci. (1992) 126.
- 156
A. S. Bommarius in
H.-J. Rehm,
G. Reed,
A. Pühler,
P. Stadler (eds.):
Biotechnology, Vol. 3,
VCH Verlagsgesellschaft,
Weinheim
1993,
pp. 427.
10.1002/9783527620845.ch17 Google Scholar
- 157 Ref. (1), pp. 379.
- 158 O. M. Birch, J. M. Brass, A. Kiener, K. Robins, D. Schmidhalter, N. M. Shaw, T. Zimmermann, Chemistry Today (1995) 9.
- 159 C. Chassin, Proc. Chiral USA (1993) 137.
- 160 E. Cerbeland, D. Petre, US 5.034.329, 1991.
- 161 E. De Vroom, Org. Proc. Res. Developm. (1998) 2, 128.
- 162 E. J. A. X. Van de Sandt, E. de Vroom, Chimica Oggi–Chemistry Today 18 (2000) no. 5, 72.
- 163 K. Matsumoto in A. Tanaka, T. Tosa, T. Kobayashi (ed.): Industrial Application of Immobilized Biocatalysts, Marcel Dekker Inc., New York 1993, pp. 67.
- 164 A. Parmar, H. Kumar, S. S. Marwaha, J. F. Kennedy, Biotechnol. Advances 18 (2000) 289.
- 165 A. Chadha, P. S. R. Babu, T. Panda, Int. J. Pharm. Adv. 1 (1995) no. 2, 216.
- 166 Y. Chisti, M. Moo-Young in V. Moses, R. E. Cape (ed.): Biotechnology: The Science and the Business, Harwood Academic Publishers, New York 1991, pp. 167.
- 167 I. S. Novella, C. Fargues, G. Grevillot, Biotechnol. Bioeng. 44 (1994) 379.
- 168 E. Katchalski-Katzir, D. M. Kraemer, J. Mol. Catal. B: Enzym. 10 (2000) 157.
- 169
A. Liese,
K. Seelbach,
C. Wandrey,
Industrial Biotransformations,
Wiley-VCH,
Weinheim,
2000,
pp. 281.
10.1002/9783527614165 Google Scholar
- 170 A. Parmar, H. Kumar, S. S. Marwaha, J. F. Kennedy, Crit. Rev. Biotechnol. 18 (1998) no. 1, 1.
- 171 Ref. (1), pp. 386 and 458.
- 172 F. Balkenhohl, K. Ditrich, B. Hauer, W. Ladner, J. Prakt. Chem. 339 (1997) 381.
- 173 U. Vagt, Chimica Oggi–Chemistry Today 16 (1998) nos. 7/8, 38.
- 174 Ref. (1), pp. 409.
- 175 A. Müller, E. Busker, J. Engel, B. Kutscher, M. Bernd, A. V. Schally, Int. J. Pept. Protein Res. (1994) 264.
- 176 S. Bajusz, V. J. Csernus, T. Janaky, L. Bokser, M. Fekete, A. V. Schally, Int. J. Pept. Protein Res. (1988) 425.
- 177
T. Reissmann,
J. Engel,
B. Kutscher,
M. Bernd,
P. Hilgard,
M. Peukert,
I. Szelenyi,
S. Reichert,
D. Gonzales-Barcena,
E. Nieschiag,
A. M. Comaru-Schally,
A. V. Schally,
Drugs Fut.
(1994)
228.
10.1358/dof.1994.019.03.238584 Google Scholar
- 178 K. Drauz, M. Kottenhahn, M. Makryaleas, H. Klenk, M. Bernd, Angew. Chem. 103 (1991) 704; Angew. Chem. Int. Ed. Engl. 30 (1991) 712.
- 179 K. Drauz, M. Kottenhahn, H. Klenk, J. Prakt. Chem. 334 (1992) 214.
- 180 A. S. Bommarius, M. Kottenhahn, H. Klenk, K. Drauz, in S. Servi (ed.): Microbial Reagents in Organic Synthesis, Kluwer Academic, Dordrecht 1992, pp. 161.
- 181 T. Fukumura, Agric. Biol. Chem. 40 (1976) 1687.
- 182 T. Fukumura, Agric. Biol. Chem. 40 (1976) 1695.
- 183 T. Fukumura, Agric. Biol. Chem. 41 (1977) 1327.
- 184 J. Crosby, Tetrahedron 1991, 4789.
- 185 S. J. C. Taylor, R. McCague, R. Wisdom, C. Lee, K. Dickson, G. Ruecroft, F. O'Brien, J. Littlechild, J. Bevan, S. M. Roberts, C. T. Evans, Tetrahedron: Asymmetry 4 (1993) 1117.
- 186 S. J. C. Taylor, R. C. Brown, P. A. Keene, I. N. Taylor, Bioorg. Med. Chem. 7 (1999) 2163.
- 187 A. Sakimae, A. Hosoi, E. Kobayashi, N. Ohsuga, R. Numazawa, I. Watanabe, H. Ohnishi, Biosci. Biotech. Biochem. 56 (1992) 1252.
- 188 A. Sakimae, R. Numazawa, H. Ohnishi, Biosci. Biotech. Biochem. 56 (1992) 1341.
- 189 Q.-M. Gu, C.-S. Chen, C. J. Sih, Tetrahedron Lett. (1986) 1763.
- 190 P. Cesti, P. Picardi, EP 195.717, 1986.
- 191 G. Fülling, M. Schlingmann, R. Keller, DE 3.919.029, 1990.
- 192 J. G. H. M. Mutsaers, H. J. Kooremann, Rec. Trav. Chim. Pays-Bas (1991) 185.
- 193 J. W. H. Smeets, A. P. G. Kienboom in S. Servi (ed.): Microbial Reagents in Organic Synthesis, Kluwer Academic, Dordrecht 1992, pp. 273.
- 194 L. A. Hulshof, J. H. Roskam (Stamicarbon B. V.), EP 343.714, 1989.
- 195 J. W. Young, R. L. Brataler, Proc. Chiral 90 Symp. Spring Innovations UK 1990, pp. 23.
- 196 M. Villa, C. Pozzoli, Proc. Chiral 95 USA Symp. Spring Innovations UK 1995, pp. 13.
- 197 K. Oyama in: Chirality in Industry, A. N. Collins, G. N. Sheldrake, J. Crosby (eds.), J. Wiley, New York 1992, pp. 237.
- 198 Ref. (1), pp. 178–261.
- 199 R. Chênevert, R. Gagnon, M. Desiardins, M. Dickman, P. Bureau, G. Fortier, R. Martin, M. Létourheau, S. Thiboutot, R. Bel-Rhlid in S. Servi (ed.): Microbial Reagents in Organic Synthesis, Kluwer Academic, Dordrecht 1992, pp. 135.
- 200 S. Shimizu, H. Yamada in E. J. Vandamme (ed.): Biotechnology of Vitamins, Pigments and Growth Factory, Elsevier Applied Science, London 1989, p. 199.
- 201 H. Yamada, S. Shimizu in: Enzyme Engineering 11, D. S. Clark, D. Estell, J. Dordick (eds.), New York Academy of Science, New York, 1992, pp. 374.
- 202 H. Yamada, Chimia (1993) 5.
- 203 M. Ress-Löschke, T. Friedrich, B. Hauer, R. Mattes, D. Engels (BASF), DE 19848129, 1998.
- 204 G. Matcham, A. Bowen, S. Lee, P. Pienkos, A. Zeitlin, Proceedings of Chiral'94 USA Symposium, Spring Innovations Ltd., 1994, p. 55.
- 205 H. Yamada, H. Kumagai, Pure Appl. Chem. 50 (1978) nos. 9–10, 1117.
- 206 H. Enei, H. Yamada, Prog. Ind. Microbiol. 24 (1986) 280.
- 207 H. G. Kulla, Chimia, (1991) 81.
- 208 A. S. Bommarius, K. Drauz, W. Hummel, M.-R. Kula, C. Wandrey, Biocatalysis 10 (1994) 37.
- 209 K. Drauz, W. Jahn, M. Schwarm, Chem. Eur. J. (1995) 538.
- 210 A. S. Bommarius, M. Schwarm, K. Stingl, M. Kottenhahn, K. Huthmacher, K. Drauz, Tetrahedron: Asymmetry 6 (1995) 2851.
- 211 P. P. Taylor, D. P. Pantaleone, R. F. Senkpeil, I. G. Fotheringham, Trends Biotechnol. 16 (1998) 412.
- 212 D. J. Ager, I. G. Fotheringham, T. Li, D. P. Pantaleone, R. F. Senkpeil, Enantiomer 5 (2000) 235.
- 213 For reviews on the asymmetric synthesis of cyanohydrins and applications thereof, see: F. Effenberger, Angew. Chem. 106 (1994) 1609.
- 214 Angew. Chem. Int. Ed. Engl. 1994, 33, 1555; R. J. H. Gregory, Chem. Rev. 99 (1999) 3649.
- 215 M. Schmidt, H. Griengl, Top. Curr. Chem. 200 (1999) 193.
- 216 M. Bauer, H. Griengl, W. Steiner, Enzyme Microb. Technol. 24 (1999) 514, and references therein.
- 217
R. L. Hill,
J. W. Teipel in
P. Boyer (ed.):
The Enzymes,
Vol. 5,
Academic Press,
New York
1971,
pp. 539.
10.1016/S1874-6047(08)60102-X Google Scholar
- 218 U. T. Bornscheuer in H.-J. Rehm, G. Reed, A. Pühler, P. Stadler (eds.): Biotechnology, Vol. 8b, Wiley-VCH, Weinheim, Germany 2000, pp. 285.
- 219 S. B. Mirviss, S. K. Dahod, M. W. Empie, Ind. Eng. Chem. Res. 29 (1990) 651.
- 220 L. Rohlin, M.-K. Oh, J. C. Liao, Curr. Opinion Mircobiol. 4 (2001) 330.
- 221 G. Chotani, T. Dodge, A. Hsu, M. Kumar, R. LaDuca, D. Trimbur, W. Weyler, K. Sanford, Biochimica et Biophysica Acta 434 (2000) 1543.
Further Reading
- R. Breslow (ed.): Artificial Enzymes, Wiley-VCH, Weinheim 2005.
-
G. Carrea
S. Riva (eds.):
Organic Synthesis with Enzymes in Non-aqueous Media,
Wiley-VCH,
Weinheim
2008.
10.1002/9783527621729 Google Scholar
- K. Drauz H. Gröger, O. May (eds.): Enzyme Catalysis in Organic Synthesis, 3rd ed., Wiley-VCH, Weinheim 2011.
-
K. Faber:
Biotransformations in Organic Chemistry,
5th ed.,
Springer,
Berlin
2004.
10.1007/978-3-642-18537-3 Google Scholar
-
E. Garcia-Junceda (ed.):
Multi-step Enzyme Catalysis - Biotransformations and Chemoenzymatic Synthesis,
Wiley-VCH,
Weinheim
2008.
10.1002/9783527623389 Google Scholar
-
V. Gotor
I. Alfonso
E. Garcia-Urdiales (eds.):
Asymmetric Organic Synthesis with Enzymes,
Wiley-VCH,
Weinheim
2008.
10.1002/9783527622481 Google Scholar
- S. Kobayashi H. Ritter D. L. Kaplan (eds.): Enzyme-Catalyzed Synthesis of Polymers, Springer, Berlin 2006.
- J. Whittall P. Sutton: Practical Methods for Biocatalysis and Biotransformations, Wiley, Chichester 2010.
-
A. Zaks:
Enzymes In Organic Synthesis,
Kirk Othmer Encyclopedia of Chemical Technology,
5th edition,
John Wiley & Sons,
Hoboken, NJ,
online: DOI: 0.1002/0471238961.0514262526011119.a01
0.1002/0471238961.0514262526011119.a01 Google Scholar
