Practical Syntheses of N-Substituted 3-Hydroxyazetidines and 4-Hydroxypiperidines by Hydroxylation with Sphingomonas sp. HXN-200

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1859-1862

  Chang, Dongliang ^a   Feiten, Hans Jürgen ^a   Engesser, Karl H ^b   Van Beilen, Jan B ^a   Witholt, Bernard ^a   Li, Zhi ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AZETIDINE DERIVATIVE; GALACTOSE OXIDASE; HYDROXYLAMINE; OXIME; PIPERIDINE DERIVATIVE; POLYMER;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR GENETICS; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ALDEHYDES; AZETIDINES; CARBOHYDRATE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GALACTOSE OXIDASE; HYDROXYLAMINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; OXIMES; PIPERIDINES; POLYMERS;

EID: 0037198750     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025829s     Document Type: Article

References (79)

1. (a) Abe, T.; Isoda, T.; Sato, C.; Mihira, A.; Tamai, S.; Kumagai T. U.S. Patent 5,534,510, 1995.
2. (b) Abe, T.; Kumagai, T. U.S. Patent 5,886,-172, 1999.
3. (c) Teng, L. C. (A. H. Robins Co., Inc.) EP 102194, 1984.
4. (d) Koike, H.; Yoshomoto, M.; Nishino, H. (Sankyo Co., Ltd.; Ube Ind., Ltd.) EP 266922, 1988.
5. (a) Prieto, J.; Vega, A.; Moragues, J.; Spickett, R. G. W. (Fordonal S.A.) U.S. Patent 4,550,116, 1985.
6. (b) Koda, A.; Kuroki, Y.; Fujiwara, H.; Takamura, S.; Yamano, K. (Ube Ind., Ltd.) EP 335586, 1989.
7. (c) Ishikawa, H.; Tabusa, F.; Miyamoto, H.; Kano, M.; Ueda, H.; Tamaoka, H.; Nakagawa, K. Chem. Pharm. Bull. 1989, 37, 2103.
8. (d) Tasaka, K. Drugs Future 1988, 13, 1056.
9. (e) Knopp, D.; Edenhofer, A.; Hadváry, P.; Weller, T.; Hürzeler, M.; Trzeciak, A.; Müller, M.; Steiner, B.; Alig, L. J. Med. Chem. 1992, 35, 4393.
10. (f) Graul, A.; Castañer, J.; Merlos, M. Drugs Future 1998, 23, 1297.
11. (a) Gaertner, V. R. J. Org. Chem. 1967, 32, 2972.
12. (b) Laguerre, M.; Boyer, C.; Leger, J.-M: Carpy, A. Can. J. Chem. 1989, 67, 1514.
13. (c) Jimenez, A.; Vega, S. J. Hererocycl. Chem. 1986, 23, 1503.
14. (d) Jung, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729.
15. (e) Constantieux, Th.; Grelier, St.; Picard, J.-P. Synlett 1998, 5, 510.
16. (f) Higgins, R. H.; Eaton, Q. L.; Worth, L.; Peterson, M. V. J. Heterocycl. Chem. 1987, 24, 255.
17. (g) Karikomi, M.; Arai, K.; Toda, T. Tetrahedron Lett. 1997, 38, 6059.
18. (h) Hayashi, K.; Sato, C.; Hiki, S.; Kumagai, T.; Tamai, S.; Abe, T.; Nagao, Y. Tetrahedron Lett. 1999, 40, 3761.
19. (i) Axenrod, T.; Watnick, C.; Yazdekhasti, H.; Dave, P. R. J. Org. Chem. 1995, 60, 1959.
20. (a) Okano, T.; Matsuoka, M.; Konishi, H.; Kiji, J. Chem. Lett. 1987, 181.
21. (b) Kostochka, L. M.; Belostotskii, A. M.; Skoldinov, A. P. J. Org. Chem. USSR (Engl. Transl.) 1982, 18, 2315.
22. (c) McElvain, S. M.; McMahon, R. E. J. Am. Chem. Soc. 1949, 71, 901.
23. (d) Bolyard, N. W. J. Am. Chem. Soc. 1930, 52, 1030.
24. (e) Grob, C. A.; Brenneisen, P. Helv: Chim. Acta 1958, 41, 1184.
25. (f) Schaefgen, J. R.; Koontz, F. H.; Tietz, R. F. J. Polym. Sci. 1959, 40, 377.
26. (g) Hall, H. K., Jr. J. Am. Chem. Soc. 1958, 80, 6412.
27. (h) Coan, S. B.; Jaffe, B.; Papa, D. J. Am. Chem. Soc. 1956, 78, 3701.
28. (i) Bowden, K.; Green, P. N. J. Chem. Soc. 1952, 1164.
29. (j) McCann, S. F.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6107.
30. (k) Larsen, S. D.; Grieso, P. A.; Fobare, W. F. J. Am. Chem. Soc. 1986, 108, 3512.
31. (l) Dicko, A.; Montury, M.; Baboulene, M. Tetrahedron Lett. 1987, 28, 6041.
32. (m) Brown, H. C.; Prasad, J. V. N. V. J. Am. Chem. Soc. 1986, 108, 2049.
33. (n) Brown, H. C.; Prasad, J. V. N. V.; Zee, S.-H. J. Org. Chem. 1985, 50, 1582.
34. For reviews, see: (a) Reiser, O. Angew. Chem., Im. Ed. Engl. 1994, 33, 69. (b) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (e) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (f) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
35. For reviews, see: (a) Reiser, O. Angew. Chem., Im. Ed. Engl. 1994, 33, 69. (b) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (e) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (f) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
36. For reviews, see: (a) Reiser, O. Angew. Chem., Im. Ed. Engl. 1994, 33, 69. (b) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (e) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (f) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
37. For reviews, see: (a) Reiser, O. Angew. Chem., Im. Ed. Engl. 1994, 33, 69. (b) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (e) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (f) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
38. For reviews, see: (a) Reiser, O. Angew. Chem., Im. Ed. Engl. 1994, 33, 69. (b) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (e) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (f) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
39. For reviews, see: (a) Reiser, O. Angew. Chem., Im. Ed. Engl. 1994, 33, 69. (b) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (c) Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314. (d) Davis, J. A.; Watson, P. L.; Liebmann, J. F.; Greenberg, A. Selective Hydrocarbon Activation; VCH: New York, 1990. (e) Hill, C. L. Activation and Functionalization of Alkanes; Wiley and Sons: New York, 1989. (f) Shilov, A. V. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reisel: Boston, 1984.
40. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
41. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
42. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
43. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
44. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
45. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
46. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
47. 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: Cambridge, 1985; p 215. (d) Holland, H. L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; Chapter 3, p 55. (e) Holland, H. L.; Weber, H. Curr. Opin. Biotechnol. 2000, 11, 547. (f) Duetz, W. A.; van Beilen, J. B.; Witholt, B. Curr. Opin. Biotechnol. 2001, 12, 419. (g) Lehman, L. R.; Stewart, J. D. Curr. Org. Chem. 2001, 5, 439. (h) 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.
48. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
49. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
50. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
51. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
52. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
53. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
54. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
55. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
56. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
57. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
58. For recent publications, see: (a) Li, Z.; Feiten, H.-J.; Chang, D.; Duetz, W. A.; van Beilen, J. B.; Witholt, B. J. Org. Chem. 2001, 66, 8424. (b) Chang, D.; Witholt, B.; Li, Z. Org. Lett. 2000, 2, 3949. (c) Li, Z.; Feiten, H.-J.; van Beilen, J. B.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323. (d) de Raadt, A.; Griengl, H.; Weber, H. J. Chem. Eur. J. 2001, 7, 27. (e) 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 2001, 57, 8151. (f) 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. (g) Aranda, G.; Moreno, L.; Cortes, M.; Prange, T.; Maurs, M.; Azerad, R. Tetrahedron 2001, 57, 6051. (h) Hemenway, M. S.; Olivo, H. F. J. Org. Chem. 1999, 64, 6312. (i) Holland, H. L.; Morris, T. A.; Nava, P. J.; Zabic, M. Tetrahedron 1999, 55, 7441. (j) Putsch, S. L.; Aitken, S. J.; Chow, C. S.-Y.; Grogan, G.; Staines, A. Bioorg. Chem. 1999, 27, 81. (k) Shibasaki, T.; Sakurai, W.; Hasegawa, A.; Uosaki, Y.; Mori, H.; Yoshida M.; Ozaki, A. Tetrahedron Lett. 1999, 40, 5227.
59. (a) Aitken, S. J.; Grogan, G.; Chow, C.; Turner, N. J.; Flitsch, S. L. J. Chem. Soc., Perkin Trans. 1 1998, 3365.
60. (b) Archelas, A.; Furstoss, R.; Srairi, D.; Maury, G. Bull. Soc. Chem. Fr. 1986, 234.
61. (c) Johnson, R. A.; Herr, M. E.; Murray, H. C.; Fonken, G. S. J. Org. Chem. 1968, 3187.
62. (d) Floyd, N.; Munyemana, F.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1993, 881.
63. Parshikov, I. A.; Modyanova, L. V.; Dovgilivich, E. V.; Terent'ev, P. B.; Vorob'eva, L. I.; Grishina, G. V. Chem. Heterocycl. Compd. (Engl. Transl.) 1992, 28, 159.
64. Lageveen, R. G.; Huisman, G. W.; Preusting, H.; Ketelaar, P.; Eggink, G.; Witholt, B. Appl. Environ. Microbiol. 1988, 54, 2924.
65. Billotte, S. Synlett 1998, 4, 379.
66. 1H NMR spectrum at 243 K indicates the existence of two rotamers due to the restricted rotation of the N-CO bond.
67. Ferrer, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron 1997, 53, 15877.
68. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109.
69. Patonay, T.; Patonay-Peli, E.; Mogyorodi, F. Synth. Commun. 1990, 20, 2865.
70. General Procedure. Substrate was added to a 10-mL suspension of the frozen/thawed cells (0.40 g with 40 mg cdw) in 50 mM K-phosphate buffer (pH = 8.0) containing glucose (2%, w/v). The mixture was shaken at 200 rpm and 30°C for 5 h. Aliquots (0.1-0.2 mL) were taken out at predetermined time points and diluted in MeOH, and the cells were removed by centrifugation. The samples were analyzed by HPLC.
71. HPLC Analysis. Column, Hypersil BDS-C18 (5 μm, 125 mm × 4 mm); eluent, a mixture of A (10 mM K-phosphate buffer, pH 7.0) and B (acetonitrile); flow, 1.0 mL/min.; detection, UV at 210, 225, and 254 nm; retention time, 2.1 min for 13, 5.4 min for 11 (A/B 70:30), 2.7 min for 14, 9.2 min for 12 (A/B 75:25), 3.0 min for 20, 5.2 min for 15 (A/B 85:15), 2.0 min for 21, 8.8 min for 16 (A/B 55:44), 1.7 min for 22, 6.6 min for 17 (A/B 55:45), 1.5 min for 23, 5.6 min for 18 (A/B 50:50), 1.5 min for 24, 5.4 min for 19 (A/B 70:30); the conversion was quantified by comparing the integrated peak areas at 210 nm of the samples with the substrate and product standards.
72. -1.
73. -1.
74. Jucker, E.; Schenker, E. (Sandoz) CH 463504, 1965).
75. Alig, L.; Edenhofer, A.; Hadvary, P.; Huerzeler, M.; Knopp, D.; Mueller, M.; Steiner, B.; Trzeciak, A.; Weller, T. J. Med. Chem. 1992, 35, 4393.
76. -1.
77. Kucznierz, R.; Grams, F.; Leinert, H.; Marzenell, K.; Engh, R.; von der Saal, W. J. Med. Chem. 1998, 41, 4983.
78. Hydroxylation of 15 with Rehydrated Lyophilized Cell Powder. Frozen/thawed cells of Sphingomonas sp. HXN-200 were lyophilized at low temperature for 3 days. For the experiment of Figure 1, the dry powder (80 mg), which was stored at 4°C for 2 weeks, was suspended in 20 mL of 50 mM K-phosphate buffer (pH = 8.0) containing glucose (2% w/v) in a 100 mL Erlenmeyer flask. Piperidine 15 (17.5 mg) was added to the suspension. The flask was shaken at 200 rpm at 30°C for 4 h, and the formation of 20 was followed by HPLC analysis. 17
79. Mischitz M.; Faber K.; Willetts, A. Biotechnol. Lett. 1995, 17, 893.