Regio- and stereoselective hydroxylation of N-substituted piperidin-2-ones with Sphingomonas sp. HXN-200

Tetrahedron Asymmetry

Volumn 13, Issue 19, 2002, Pages 2141-2147

  Chang, Dongliang ^a   Feiten, Hans Jürgen ^a   Witholt, Bernard ^a   Li, Zhi ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; BIOCATALYST; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THAWING; ULTRAVIOLET SPECTROSCOPY;

EID: 0037020414     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00534-7     Document Type: Article

References (69)

1. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
2. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
3. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
4. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
5. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
6. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
7. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
8. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
9. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
10. For reviews, see: (a) Labinger, J. M.; Bercaw, J. E. Nature 2002, 417, 507; (b) Costas, M.; Chen, K.; Que, L., Jr. Coordination Chem. Reviews 2000, 200-202, 517; (c) Sen, A. Acc. Chem. Res. 1998, 31, 550; (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181; (e) Reiser, O. Angew. Chem., Int. Ed. Engl. 1994, 33, 69; (f) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504; (g) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314; (h) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990; (i) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989; (j) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
11. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
12. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
13. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
14. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
15. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
16. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
17. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
18. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
19. For reviews, see: (a) Johnson, R. A. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p. 131; (b) Kieslich, K. Microbial Transformation of non-Steroid Cyclic Compounds, Thieme: Stuttgart, 1976, p. 365; (c) Furstoss R.; Archelas, A.; Fourneron, J. D.; Vigne, B. In Organic Synthesis: an Interdisciplinary Challenge; Streith, J.; Prinzbach, H.; Schill, G., Eds.; Blackwell Scientific Publications, 1985; p. 215; (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, NY, 1992; Chapter 3, p. 55; (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547; (f) Holland, H. L. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker, 2000; Chapter 5, p. 131; (g) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419; (h) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439; (i) Li, Z.; van Beilen, J. B.; Duetz, W. A.; Schmid, A.; de Raadt, A.; Griengl, H.; Witholt, B. Curr. Opin. Chem. Biol. 2002, 6, 136.
20. de Raadt A., Griengl H., Weber H.J. Chem. Eur. J. 7:2001;27.
21. de Raadt A., Fetz B., Griengl H., Klingler M.F., Krenn B., Mereiter K., Münzer D.F., Plachota P., Weber H.J., Saf R. Tetrahedron. 57:2001;8151.
22. de Raadt A., Fetz B., Griengl H., Klingler M.F., Kopper I., Krenn B., Münzer D.F., Ott R.G., Plachota P., Weber H.J., Braunegg G., Mosler W., Saf R. Eur. J. Org. Chem. 2000;3835.
23. Braunegg G., de Raadt A., Feichtenhofer S., Griengl H., Kopper I., Lehmann A., Weber H.J. Angew. Chem., Int. Ed. Engl. 38:1999;2763.
24. Aranda G., Moreno L., Cortes M., Prange T., Maurs M., Azerad R. Tetrahedron. 57:2001;6051.
25. Hemenway M.S., Olivo H.F. J. Org. Chem. 64:1999;6312.
26. Holland H.L., Morris T.A., Nava P.J., Zabic M. Tetrahedron. 55:1999;7441.
27. Flitsch S.L., Aitken S.J., Chow C.S.-Y., Grogan G., Staines A. Bioorg. Chem. 27:1999;81.
28. Aitken S.J., Grogan G., Chow C., Turner N.J., Flitsch S.L. J. Chem. Soc., Perkin Trans. 1. 1998;3365.
29. Haufe G., Wölker D., Fröhlich R. J. Org. Chem. 67:2002;3022.
30. Pietz S., Fröhlich R., Haufe G. Tetrahedron. 53:1997;17055.
31. Pietz S., Wölker D., Haufe G. Tetrahedron. 53:1997;17067.
32. Davis C.R., Johnson R.A., Cialdella J.I., Liggett W.F., Mizsak S.A., Marshall V.P. J. Org. Chem. 62:1997;2244.
33. Davis C.R., Johnson R.A., Cialdella J.I., Liggett W.F., Mizsak S.A., Han F., Marshall V.P. J. Org. Chem. 62:1997;2252.
34. Palmer C.F., Webb B., Broad S., Casson S., McCague R., Willetts A.J., Roberts S.M. Bioorg. Med. Chem. Lett. 7:1997;1299.
35. Ridyard C.H., Whittaker R.A., Higgins S.D., Roberts S.M., Willetts A.J., Bailey P.D., Rosair G.M. J. Chem. Soc., Perkin Trans. 2. 1996;1811.
36. Floyd N., Munyemana F., Roberts S.M., Willetts A.J. J. Chem. Soc., Perkin Trans. 1. 1993;881.
37. Vigne B., Archelas A., Furstoss R. Tetrahedron. 47:1991;1447.
38. Fourneron J.D., Archelas A., Vigne B., Furstoss R. Tetrahedron. 43:1987;2273.
39. Archelas A., Fourneron J.D., Vigne B., Furstoss R. Tetrahedron. 42:1986;3863.
40. Vigne B., Archelas A., Fourneron J.D., Furstoss R. Tetrahedron. 42:1986;2451.
41. Archelas A., Furstoss R., Srairi D., Maury G. Bull. Soc. Chem. Fr. 1986;234.
42. Poulos T.L., Finzel B.C., Howard A.J. J. Mol. Biol. 195:1987;697 Shimada, H.; Sligar, S. G.; Yeom, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, 1997; Chapter 5, p. 195.
43. Ravichandran K.G., Boddupalli S.S., Hasemann C.A., Peterson J.A., Deisenhofer J. Science. 261:1993;731.
44. Oliver C.F., Sandeep M., Sutcliffe M.J., Primrose W.U., Lian L.Y., Roberts G.C.K. Biochemistry. 36:1997;1567.
45. Wen L.P., Fulco A.J. J. Biol. Chem. 262:1987;6676.
46. Schwaneberg U., Appel D., Schmitt J., Schmid R.D. J. Biotech. 84:2000;249.
47. Rosenzweig A.C., Frederick C.A., Lippard S.J., Nordlung P. Nature. 366:1993;537 Kodera, M.; Kano, K.; Funabiki, T. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, 1997; Chapter 7, p. 283.
48. Merkx M., Kopp D.A., Sazinsky M.H., Blazyk J.L., Muller J., Lippard S.J. Angew. Chem., Int. Ed. 40:2001;2782.
49. Yoshizawa K. J. Inorg. Biochem. 78:2000;23.
50. Peterson J.A., Basu D., Coon M.J. J. Biol. Chem. 241:1966;5162.
51. Kok M., Oldenhuis R., van der Linden M.P.G., Raatjes P., Kingma J., van Lelyveld P.H., Witholt B. J. Biol. Chem. 264:1989;5435.
52. van Beilen J.B., Penninga D., Witholt B. J. Biol. Chem. 267:1992;9194.
53. van Beilen J.B., Kingma J., Witholt B. Enzyme Microb. Technol. 16:1994;904.
54. Chang D., Feiten H.-J., Engesser K.-H., van Beilen J.B., Witholt B., Li Z. Org. Lett. 4:2002;1859.
55. Li Z., Feiten H.-J., Chang D., Duetz W.A., van Beilen J.B., Witholt B. J. Org. Chem. 66:2001;8424.
56. Chang D., Witholt B., Li Z. Org. Lett. 2:2000;3949.
57. Li Z., Feiten H.-J., van Beilen J.B., Duetz W., Witholt B. Tetrahedron: Asymmetry. 10:1999;1323.
58. Otake N., Takeuchi S., Endo T., Yonehara H. Tetrahedron Lett. 1965;1411.
59. Yonehara H., Otake N. Tetrahedron Lett. 1966;3785.
60. Nishi T., Higashi K., Soga T., Takemura M., Sato M. J. Antibiotics. 47:1994;357.
61. Michel D., Glänzel M., Waibel R., Gmeiner P. Heterocycles. 51:1999;1389.
62. Weber K., Ohnmacht U., Gmeliner P. J. Org. Chem. 65:2000;7406.
63. Weber K., Gmeiner P. Syn. Lett. 1998;885.
64. Moehrle H., Ottersbach D. Arch. Pharm. (Weinheim Ger.). 323:1990;109.
65. Moehrle H., Jeandree M., Breitmaier E., Rohonczy J. J. Prakt. Chem. 342:2000;473.
66. Nakagawa M., Torisawa Y., Hosaka T., Tanabe K., Tavet F., Aikawa M., Hino T. Heterocycles. 35:1993;1157.
67. Minami N.K., Reiner J.E., Semple J.E. Bioorg. Med. Chem. Lett. 9:1999;2625.
68. Lageveen R.G., Huisman G.W., Preusting H., Ketelaar P., Eggink G., Witholt B. Appl. Environ. Microbiol. 54:1988;2924.
69. Takano S., Yuta K., Hatakeyama S., Ogasawara K. Tetrahedron Lett. 4:1979;369.