Empirical rules for the enantiopreference of lipase from Aspergillus niger toward secondary alcohols and carboxylic acids, especially α-amino acids

Tetrahedron Asymmetry

Volumn 8, Issue 22, 1997, Pages 3719-3733

  Janes, Lana E ^a   Kazlauskas, Romas J ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; ASPERGILLUS NIGER; DRUG PURIFICATION; ENANTIOMER; ENZYME ACTIVITY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0030732640     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00524-7     Document Type: Article

References (45)

1. (a) Roberts, S. M. Preparative Biotransformations, Wiley: Chichester, 1992-1997.
2. (b) Faber, K. Biotransformations in Organic Chemistry, 3rd edn, Springer: Weinheim, 1997.
3. (c) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Elsevier Science: New York, 1994.
4. Itoh, T.; Kuroda, K.; Tomosada, M.; Takagi, Y. J. Org. Chem. 1991, 56, 797-804.
5. Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665.
6. Ahmed, S. N.; Kazlauskas, R. J.; Morinville, A. H.; Grochulski, P.; Schrag, J. D.; Cygler, M. Biocatalysis 1994, 9, 209-225; Franssen, M. C. R.; Jongejan, H.; Kooijman, H.; Spek, A. L.; Camacho Mondril, N. L. F. L.; Boavida dos Santos, P. M. A. C.; de Groot, A. Tetrahedron: Asymmetry 1996, 7, 497-510.
7. Ahmed, S. N.; Kazlauskas, R. J.; Morinville, A. H.; Grochulski, P.; Schrag, J. D.; Cygler, M. Biocatalysis 1994, 9, 209-225; Franssen, M. C. R.; Jongejan, H.; Kooijman, H.; Spek, A. L.; Camacho Mondril, N. L. F. L.; Boavida dos Santos, P. M. A. C.; de Groot, A. Tetrahedron: Asymmetry 1996, 7, 497-510.
8. Cygler, M.; Grochulski, P.; Kazlauskas, R. J.; Schrag, J. D.; Bouthillier, F.; Rubin, B.; Serreqi, A. N.; Gupta, A. K. J. Am. Chem. Soc. 1994, 116, 3180-3186.
9. We omitted one reported resolution of 3-benzoylthio-2-methylpropanoic acid from Table 2 (Gu, Q. M.; Reddy, D. R.; Sih, C. J. Tetrahedron Lett. 1986, 27, 5203-5206). The authors used Amano lipase K-10, but later reports from this group indicate that this lipase is a Pseudomonas lipase, not ANL.
10. Table 2, reference e. 8. We assayed three lipases and acetylcholine esterase following a standard procedure: Eisenthal, R.; Danson, M. J. Enzyme Assays, IRL: Oxford, 1992, p. 81.
11. Review: van den Hombergh, J. P. T., van de Vondervoort, P. J. I., Fraissinet-Tachet, L., Visser, J. Trends Biotechnol. 1997, 15, 256-263. Examples: Kugami, I.; Yamasaki, M.; Ui, N. Biochim. Biophys. Acta 1981, 659, 334-343; Dal Degan, F.; Ribadeau-Dumas, B.; Breddam, K. Appl. Environ. Microbiol. 1992, 2144-2152; Krishnan, S.; Vijayalakshmi, M. A. J. Chromatogr. 1986, 570, 315-326.
12. Review: van den Hombergh, J. P. T., van de Vondervoort, P. J. I., Fraissinet-Tachet, L., Visser, J. Trends Biotechnol. 1997, 15, 256-263. Examples: Kugami, I.; Yamasaki, M.; Ui, N. Biochim. Biophys. Acta 1981, 659, 334-343; Dal Degan, F.; Ribadeau-Dumas, B.; Breddam, K. Appl. Environ. Microbiol. 1992, 2144-2152; Krishnan, S.; Vijayalakshmi, M. A. J. Chromatogr. 1986, 570, 315-326.
13. Review: van den Hombergh, J. P. T., van de Vondervoort, P. J. I., Fraissinet-Tachet, L., Visser, J. Trends Biotechnol. 1997, 15, 256-263. Examples: Kugami, I.; Yamasaki, M.; Ui, N. Biochim. Biophys. Acta 1981, 659, 334-343; Dal Degan, F.; Ribadeau-Dumas, B.; Breddam, K. Appl. Environ. Microbiol. 1992, 2144-2152; Krishnan, S.; Vijayalakshmi, M. A. J. Chromatogr. 1986, 570, 315-326.
14. Review: van den Hombergh, J. P. T., van de Vondervoort, P. J. I., Fraissinet-Tachet, L., Visser, J. Trends Biotechnol. 1997, 15, 256-263. Examples: Kugami, I.; Yamasaki, M.; Ui, N. Biochim. Biophys. Acta 1981, 659, 334-343; Dal Degan, F.; Ribadeau-Dumas, B.; Breddam, K. Appl. Environ. Microbiol. 1992, 2144-2152; Krishnan, S.; Vijayalakshmi, M. A. J. Chromatogr. 1986, 570, 315-326.
15. Kazlauskas, R. J.; Weissfloch, A. N. E. J. Mol. Catal. B Enz. 1997, 3, 65-72.
16. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
17. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
18. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
19. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
20. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
21. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
22. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
23. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
24. Fukumoto, J.; Iwai, M.; Tsujisaka, Y. J. Gen. Appl. Microb. 1963, 9, 353-361; Chang, S.-H. Bull. Int. Chem. Acad. Sci. 1973, 22, 17-24; Pal, N.; Das, S.; Kundu, A. K. J. Ferment. Technol. 1978, 56, 593-598; Tombs, M. P.; Blake, G. G. Biochim. Biophys. Acta. 1982, 700, 81-89; Hofelmann, M.; Hartmann, J.; Zink, A.; Schreier, P. J. Food. Sci. 1985, 50, 1721-1725; Sugihara, A.; Shimada, Y.; Tominaga, Y. Agric. Biol. Chem. 1988, 52, 1591-1592; Torossian, K.; Bell, A. W. Biotechnol. Appl. Biochem. 1991, 13, 205-211; Chen, H.-P.; Hsaio, K.-F.; Wang, K.-T. Biotechnol. Lett. 1995, 17, 305-308; Pokorny, D.; Cimerman, A.; Steiner, W. J. Mol. Catal. B Enz. 1997, 2, 215-222.
25. Carrea, G.; Corcelli, A.; Pamisano, G.; Riva, S. Biotechnol. Bioengineer. 1996, 52, 648-652.
26. Wigley, R. C. In Industrial Enzymology, 2nd edn; Godfrey, T.; West, S., Eds; Stockton: New York, 1996, pp. 133-154.
27. Reference 1c, pp. 60-64.
28. Liu, W.; Ray, P.; Benezra, S. A. J. Chem. Soc., Perkin Trans, 1 1995, 553-559.
29. 2-aryl. This selectivity is similar to that for chymotrypsin, a known impurity in crude PPL.
30. 2-aryl. This selectivity is similar to that for chymotrypsin, a known impurity in crude PPL.
31. Rotticci, D.; Orrenius, C.; Huit, K.; Norin, T. Tetrahedron: Asymmetry 1997, 8, 359-362.
32. West, J. B.; Wong, C.-H. Tetrahedron Lett. 1987, 28, 1629-1632; Wong, C.-H.; Wang, K.-T. Experientia 1991, 47, 1123-1129; Margolin, A. L.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3804-3805; Ohshiro, T.; Mochida, K.; Uwajima, T. Biotechnology Lett. 1992, 14, 175-178.
33. West, J. B.; Wong, C.-H. Tetrahedron Lett. 1987, 28, 1629-1632; Wong, C.-H.; Wang, K.-T. Experientia 1991, 47, 1123-1129; Margolin, A. L.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3804-3805; Ohshiro, T.; Mochida, K.; Uwajima, T. Biotechnology Lett. 1992, 14, 175-178.
34. West, J. B.; Wong, C.-H. Tetrahedron Lett. 1987, 28, 1629-1632; Wong, C.-H.; Wang, K.-T. Experientia 1991, 47, 1123-1129; Margolin, A. L.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3804-3805; Ohshiro, T.; Mochida, K.; Uwajima, T. Biotechnology Lett. 1992, 14, 175-178.
35. West, J. B.; Wong, C.-H. Tetrahedron Lett. 1987, 28, 1629-1632; Wong, C.-H.; Wang, K.-T. Experientia 1991, 47, 1123-1129; Margolin, A. L.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3804-3805; Ohshiro, T.; Mochida, K.; Uwajima, T. Biotechnology Lett. 1992, 14, 175-178.
36. Fischer, E.; Scheibler, H. Liebigs Ann. Chem. 1911, 383, 346.
37. Pitzele, B. S.; Hamilton, R. W.; Kudla, K. D.; Tsymbalov, S.; Stapelford, A.; Savage, M. A.; Clare, M.; Hammond, D. L.; Hansen, D. W. J. Med. Chem. 1994, 37, 888-896.
38. Moersch, G. W.; Rebstock, M. C.; Wittle, E. L.; Tinney, F. J.; Nicholaides, E. D.; Hutt, M. P.; Mich, T. F.; Vandenbelt, J. M. J. Med. Chem. 1979, 22, 935-943.
39. Brenner, M.; Huber, W. Helv. Chim. Acta 1953, 36, 1109-1113.
40. Obrecht, D.; Spiegler, C.; Schonholzer, P.; Muller, K. Helv. Chim. Acta 1992, 75, 1665-1696.
41. Bodansky, M.; Bodansky, A. The Practice of Peptide Synthesis; 2nd edn, Springer: Berlin, 1994, p. 11.
42. Ref. 24, p. 118.
43. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
44. Hilton, M.; Armstrong, D. W. J. Liquid Chromatog. 1991, 14, 9-28.
45. Colton, I. J.; Ahmed, S. N.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 212-217.