Resolution of non-protein amino acids via microbial protease-catalyzed ester hydrolysis: Marked enhancement of enantioselectivity by the use of esters with longer alkyl chains and at low temperature

Tetrahedron Asymmetry

Volumn 8, Issue 3, 1997, Pages 367-370

  Miyazawa, Toshifumi ^a   Minowa, Hiroe ^a   Miyamoto, Toyoko ^a   Imagawa, Kiwamu ^a   Yanagihara, Ryoji ^a   Yamada, Takashi ^a  

^a KONAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; MICROBIAL ENZYME; PROTEINASE;

ARTICLE; ASPERGILLUS; CATALYSIS; CHEMICAL REACTION; HYDROLYSIS; PRIORITY JOURNAL; STEREOISOMERISM; TEMPERATURE;

EID: 0031040605     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00002-5     Document Type: Article

References (23)

1. So far the enantioselective hydrolysis of carboxylic acid esters and the regioselective acylation of sugar substrates have been carried out using these microbial proteases: G. Fulling and C. J. Sih, J. Am. Chem. Soc., 1987, 109, 2845; C. Feichter, K. Faber and H. Griengl, J. Chem. Soc., Perkin Trans. 1, 1991, 653; M.-J. Kim, W. J. Hennen, H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 1988, 110, 6481; G. Carrea, S. Riva and F. Secundo, J. Chem. Soc., Perkin Trans. 1, 1989, 1057.
2. So far the enantioselective hydrolysis of carboxylic acid esters and the regioselective acylation of sugar substrates have been carried out using these microbial proteases: G. Fulling and C. J. Sih, J. Am. Chem. Soc., 1987, 109, 2845; C. Feichter, K. Faber and H. Griengl, J. Chem. Soc., Perkin Trans. 1, 1991, 653; M.-J. Kim, W. J. Hennen, H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 1988, 110, 6481; G. Carrea, S. Riva and F. Secundo, J. Chem. Soc., Perkin Trans. 1, 1989, 1057.
3. So far the enantioselective hydrolysis of carboxylic acid esters and the regioselective acylation of sugar substrates have been carried out using these microbial proteases: G. Fulling and C. J. Sih, J. Am. Chem. Soc., 1987, 109, 2845; C. Feichter, K. Faber and H. Griengl, J. Chem. Soc., Perkin Trans. 1, 1991, 653; M.-J. Kim, W. J. Hennen, H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 1988, 110, 6481; G. Carrea, S. Riva and F. Secundo, J. Chem. Soc., Perkin Trans. 1, 1989, 1057.
4. So far the enantioselective hydrolysis of carboxylic acid esters and the regioselective acylation of sugar substrates have been carried out using these microbial proteases: G. Fulling and C. J. Sih, J. Am. Chem. Soc., 1987, 109, 2845; C. Feichter, K. Faber and H. Griengl, J. Chem. Soc., Perkin Trans. 1, 1991, 653; M.-J. Kim, W. J. Hennen, H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 1988, 110, 6481; G. Carrea, S. Riva and F. Secundo, J. Chem. Soc., Perkin Trans. 1, 1989, 1057.
5. We have reported the resolution of non-protein amino acids through the enantioselective hydrolysis of their N-protected methyl esters. In some cases, however, the hydrolysis rates were rather slow: T. Miyazawa, H. Iwanaga, T. Yamada and S. Kuwata, Chirality, 1992, 4, 427; T. Miyazawa, H. Iwanaga, T. Yamada and S. Kuwata, Biotechnol. Lett., 1994, 16, 373; T. Miyazawa, in Fluorine-Containing Amino Acids: Synthesis and Properties, eds. V. P. Kukhar' and V. A. Soloshonok, Wiley, Chichester, 1995, Chap. 7.
6. We have reported the resolution of non-protein amino acids through the enantioselective hydrolysis of their N-protected methyl esters. In some cases, however, the hydrolysis rates were rather slow: T. Miyazawa, H. Iwanaga, T. Yamada and S. Kuwata, Chirality, 1992, 4, 427; T. Miyazawa, H. Iwanaga, T. Yamada and S. Kuwata, Biotechnol. Lett., 1994, 16, 373; T. Miyazawa, in Fluorine-Containing Amino Acids: Synthesis and Properties, eds. V. P. Kukhar' and V. A. Soloshonok, Wiley, Chichester, 1995, Chap. 7.
7. We have reported the resolution of non-protein amino acids through the enantioselective hydrolysis of their N-protected methyl esters. In some cases, however, the hydrolysis rates were rather slow: T. Miyazawa, H. Iwanaga, T. Yamada and S. Kuwata, Chirality, 1992, 4, 427; T. Miyazawa, H. Iwanaga, T. Yamada and S. Kuwata, Biotechnol. Lett., 1994, 16, 373; T. Miyazawa, in Fluorine-Containing Amino Acids: Synthesis and Properties, eds. V. P. Kukhar' and V. A. Soloshonok, Wiley, Chichester, 1995, Chap. 7.
8. Protease A and protease N were from Amano Pharmaceutical Co. and α-chymotrypsin (Type II, ex bovine pancreas) from Sigma Chemical Co.
9. C.-S. Chen, Y. Fujimoto, G. Girdaukas and C. J. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
10. In all the cases studied here, the preferential hydrolysis of the l-enantiomers was confirmed by direct comparison with authentic samples or suggested from the regularity of elution order of amino acid enantiomers on HPLC.
11. Isobutyl esters were chosen in order to avoid the use of stinking n-butyl alcohol for preparing n-butyl esters. Amino acid esters of various kinds were prepared by a modification of the method for preparing methyl esters (M. Brenner and W. Huber, Helv. Chim. Acta, 1953, 36, 1109).
12. 2) isobutyl ester.
13. In the lipase-or esterase-catalyzed enantioselective hydrolysis of carboxylic acid esters, relevant data concerning the influence of the ester grouping on enantioselection have sometimes been seen in the literature: U. T. Bhalerao, L. Dasaradhi, P. Neelakantan and N. W. Fadnavis, J. Chem. Soc., Chem. Commun, 1991, 1197; P. Kalaritis, R. W. Regenye, J. J. Partridge and D. L. Coffen, J. Org. Chem., 1990, 55, 812; D. Bianchi, W. Cabri, P. Cesti, F. Francalanci and M. Ricci, J. Org. Chem., 1988, 53, 104; C. H. Senanayake, T. J. Bill, R. D. Larsen, J. Leazer and P. J. Reider, Tetrahedron Lett., 1992, 33, 5901. Furthermore, in the yeast reduction of β-keto esters, the inversion of enantioselectivity by modifying the size of the ester grouping has been reported: W.-R. Shieh, A. S. Gopalan and C. J. Sih, J. Am. Chem. Soc., 1985, 107, 2993; B. Zhou, A. S. Gopalan, F. VanMiddlesworth, W.-R. Shieh and C. J. Sih, J. Am. Chem. Soc., 1983, 105, 5925.
14. In the lipase-or esterase-catalyzed enantioselective hydrolysis of carboxylic acid esters, relevant data concerning the influence of the ester grouping on enantioselection have sometimes been seen in the literature: U. T. Bhalerao, L. Dasaradhi, P. Neelakantan and N. W. Fadnavis, J. Chem. Soc., Chem. Commun, 1991, 1197; P. Kalaritis, R. W. Regenye, J. J. Partridge and D. L. Coffen, J. Org. Chem., 1990, 55, 812; D. Bianchi, W. Cabri, P. Cesti, F. Francalanci and M. Ricci, J. Org. Chem., 1988, 53, 104; C. H. Senanayake, T. J. Bill, R. D. Larsen, J. Leazer and P. J. Reider, Tetrahedron Lett., 1992, 33, 5901. Furthermore, in the yeast reduction of β-keto esters, the inversion of enantioselectivity by modifying the size of the ester grouping has been reported: W.-R. Shieh, A. S. Gopalan and C. J. Sih, J. Am. Chem. Soc., 1985, 107, 2993; B. Zhou, A. S. Gopalan, F. VanMiddlesworth, W.-R. Shieh and C. J. Sih, J. Am. Chem. Soc., 1983, 105, 5925.
15. In the lipase-or esterase-catalyzed enantioselective hydrolysis of carboxylic acid esters, relevant data concerning the influence of the ester grouping on enantioselection have sometimes been seen in the literature: U. T. Bhalerao, L. Dasaradhi, P. Neelakantan and N. W. Fadnavis, J. Chem. Soc., Chem. Commun, 1991, 1197; P. Kalaritis, R. W. Regenye, J. J. Partridge and D. L. Coffen, J. Org. Chem., 1990, 55, 812; D. Bianchi, W. Cabri, P. Cesti, F. Francalanci and M. Ricci, J. Org. Chem., 1988, 53, 104; C. H. Senanayake, T. J. Bill, R. D. Larsen, J. Leazer and P. J. Reider, Tetrahedron Lett., 1992, 33, 5901. Furthermore, in the yeast reduction of β-keto esters, the inversion of enantioselectivity by modifying the size of the ester grouping has been reported: W.-R. Shieh, A. S. Gopalan and C. J. Sih, J. Am. Chem. Soc., 1985, 107, 2993; B. Zhou, A. S. Gopalan, F. VanMiddlesworth, W.-R. Shieh and C. J. Sih, J. Am. Chem. Soc., 1983, 105, 5925.
16. In the lipase-or esterase-catalyzed enantioselective hydrolysis of carboxylic acid esters, relevant data concerning the influence of the ester grouping on enantioselection have sometimes been seen in the literature: U. T. Bhalerao, L. Dasaradhi, P. Neelakantan and N. W. Fadnavis, J. Chem. Soc., Chem. Commun, 1991, 1197; P. Kalaritis, R. W. Regenye, J. J. Partridge and D. L. Coffen, J. Org. Chem., 1990, 55, 812; D. Bianchi, W. Cabri, P. Cesti, F. Francalanci and M. Ricci, J. Org. Chem., 1988, 53, 104; C. H. Senanayake, T. J. Bill, R. D. Larsen, J. Leazer and P. J. Reider, Tetrahedron Lett., 1992, 33, 5901. Furthermore, in the yeast reduction of β-keto esters, the inversion of enantioselectivity by modifying the size of the ester grouping has been reported: W.-R. Shieh, A. S. Gopalan and C. J. Sih, J. Am. Chem. Soc., 1985, 107, 2993; B. Zhou, A. S. Gopalan, F. VanMiddlesworth, W.-R. Shieh and C. J. Sih, J. Am. Chem. Soc., 1983, 105, 5925.
17. In the lipase-or esterase-catalyzed enantioselective hydrolysis of carboxylic acid esters, relevant data concerning the influence of the ester grouping on enantioselection have sometimes been seen in the literature: U. T. Bhalerao, L. Dasaradhi, P. Neelakantan and N. W. Fadnavis, J. Chem. Soc., Chem. Commun, 1991, 1197; P. Kalaritis, R. W. Regenye, J. J. Partridge and D. L. Coffen, J. Org. Chem., 1990, 55, 812; D. Bianchi, W. Cabri, P. Cesti, F. Francalanci and M. Ricci, J. Org. Chem., 1988, 53, 104; C. H. Senanayake, T. J. Bill, R. D. Larsen, J. Leazer and P. J. Reider, Tetrahedron Lett., 1992, 33, 5901. Furthermore, in the yeast reduction of β-keto esters, the inversion of enantioselectivity by modifying the size of the ester grouping has been reported: W.-R. Shieh, A. S. Gopalan and C. J. Sih, J. Am. Chem. Soc., 1985, 107, 2993; B. Zhou, A. S. Gopalan, F. VanMiddlesworth, W.-R. Shieh and C. J. Sih, J. Am. Chem. Soc., 1983, 105, 5925.
18. In the lipase-or esterase-catalyzed enantioselective hydrolysis of carboxylic acid esters, relevant data concerning the influence of the ester grouping on enantioselection have sometimes been seen in the literature: U. T. Bhalerao, L. Dasaradhi, P. Neelakantan and N. W. Fadnavis, J. Chem. Soc., Chem. Commun, 1991, 1197; P. Kalaritis, R. W. Regenye, J. J. Partridge and D. L. Coffen, J. Org. Chem., 1990, 55, 812; D. Bianchi, W. Cabri, P. Cesti, F. Francalanci and M. Ricci, J. Org. Chem., 1988, 53, 104; C. H. Senanayake, T. J. Bill, R. D. Larsen, J. Leazer and P. J. Reider, Tetrahedron Lett., 1992, 33, 5901. Furthermore, in the yeast reduction of β-keto esters, the inversion of enantioselectivity by modifying the size of the ester grouping has been reported: W.-R. Shieh, A. S. Gopalan and C. J. Sih, J. Am. Chem. Soc., 1985, 107, 2993; B. Zhou, A. S. Gopalan, F. VanMiddlesworth, W.-R. Shieh and C. J. Sih, J. Am. Chem. Soc., 1983, 105, 5925.
19. J. H. Tong, C. Petitclerc, A. D'Iorio and N. L. Benoiton, Can. J. Biochem., 1971, 49, 877.
20. 9 though there is the difference of the methyl ester from the ethyl ester.
21. Some experimental results concerning the temperature effects on the enantioselectivity of enzymatic hydrolyses have been reported: L. K. P. Lam, R. A. H. F. Hui and J. B. Jones, J. Org. Chem., 1986, 51, 2047; J. Boutelje, M. Hjalmarsson, K. Hult, M. Lindbäck and T. Norin, Bioorg. Chem., 1988, 16, 364; E. Holmberg and K. Huit, Biotechnol. Lett, 1991, 13, 323.
22. Some experimental results concerning the temperature effects on the enantioselectivity of enzymatic hydrolyses have been reported: L. K. P. Lam, R. A. H. F. Hui and J. B. Jones, J. Org. Chem., 1986, 51, 2047; J. Boutelje, M. Hjalmarsson, K. Hult, M. Lindbäck and T. Norin, Bioorg. Chem., 1988, 16, 364; E. Holmberg and K. Huit, Biotechnol. Lett, 1991, 13, 323.
23. Some experimental results concerning the temperature effects on the enantioselectivity of enzymatic hydrolyses have been reported: L. K. P. Lam, R. A. H. F. Hui and J. B. Jones, J. Org. Chem., 1986, 51, 2047; J. Boutelje, M. Hjalmarsson, K. Hult, M. Lindbäck and T. Norin, Bioorg. Chem., 1988, 16, 364; E. Holmberg and K. Huit, Biotechnol. Lett, 1991, 13, 323.