Cross-linked crystals of subtilisin: Versatile catalyst for organic synthesis

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3488-3495

  Wang, Yi Fong ^a   Yakovlevsky, Kirill ^a   Zhang, Bailing ^a   Margolin, Alexey L ^a  

^a Altus Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SUBTILISIN;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTALLIZATION; ENZYME ACTIVITY; ENZYME STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS;

EID: 0030914481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9618334     Document Type: Article

References (40)

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31. For examples for the resolution of organic molecules with subtilisin see: (a) Mazdiyasni, H.; Konopacki, D. B.; Dickman, D. A.; Zydowsky, T. M. Tetrahedron Lett. 1993, 34, 435. (b) Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094. (c) Fitzpatrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1991, 113, 3166.
32. For examples for the resolution of organic molecules with subtilisin see: (a) Mazdiyasni, H.; Konopacki, D. B.; Dickman, D. A.; Zydowsky, T. M. Tetrahedron Lett. 1993, 34, 435. (b) Kitaguchi, H.; Fitzpatrick, P. A.; Huber, J. E.; Klibanov, A. M. J. Am. Chem. Soc. 1989, 111, 3094. (c) Fitzpatrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1991, 113, 3166.
33. For examples for the regioselective reactions with subtilisin see: (a) Wu, S.-H.; Lo, L.-C.; Chen, S.-T.; Wang, K.-T. J. Org. Chem. 1989, 54, 4220, (b) Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849. (c) Singh, H. K.; Cote, G. L.; Sikorski, R. S. Tetrahedron Lett. 1993, 34, 5201. (d) Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584. (e) Riva, S.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 3291.
34. For examples for the regioselective reactions with subtilisin see: (a) Wu, S.-H.; Lo, L.-C.; Chen, S.-T.; Wang, K.-T. J. Org. Chem. 1989, 54, 4220, (b) Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849. (c) Singh, H. K.; Cote, G. L.; Sikorski, R. S. Tetrahedron Lett. 1993, 34, 5201. (d) Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584. (e) Riva, S.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 3291.
35. For examples for the regioselective reactions with subtilisin see: (a) Wu, S.-H.; Lo, L.-C.; Chen, S.-T.; Wang, K.-T. J. Org. Chem. 1989, 54, 4220, (b) Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849. (c) Singh, H. K.; Cote, G. L.; Sikorski, R. S. Tetrahedron Lett. 1993, 34, 5201. (d) Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584. (e) Riva, S.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 3291.
36. For examples for the regioselective reactions with subtilisin see: (a) Wu, S.-H.; Lo, L.-C.; Chen, S.-T.; Wang, K.-T. J. Org. Chem. 1989, 54, 4220, (b) Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849. (c) Singh, H. K.; Cote, G. L.; Sikorski, R. S. Tetrahedron Lett. 1993, 34, 5201. (d) Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584. (e) Riva, S.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 3291.
37. For examples for the regioselective reactions with subtilisin see: (a) Wu, S.-H.; Lo, L.-C.; Chen, S.-T.; Wang, K.-T. J. Org. Chem. 1989, 54, 4220, (b) Margolin, A. L.; Delinck, D. L.; Whalon, M. R. J. Am. Chem. Soc. 1990, 112, 2849. (c) Singh, H. K.; Cote, G. L.; Sikorski, R. S. Tetrahedron Lett. 1993, 34, 5201. (d) Riva, S.; Chopineau, J.; Kieboom, A. P. G.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 584. (e) Riva, S.; Klibanov, A. M. J. Am. Chem. Soc. 1988, 110, 3291.
38. After each reaction cycle, the catalysts were filtered off and washed with 3-methyl-3-pentanol. The washed catalysts were directly used in the next cycle.
39. The dry crude alcalase was prepared according to the procedure described in ref 12b.
40. Tüchsen, E.; Ottesen, M. Carlsberg Res. Commun. 1977, 42, 407.