Lipase-catalyzed enantioselective hydrolysis of N-protected racemic non-protein amino acid esters

Biocatalysis and Biotransformation

Volumn 26, Issue 3, 2008, Pages 186-196

  Kagawa, Ken Ichi ^a   Matsubara, Teruhiko ^b   Kawashiro, Katsuhiro ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Carbamoylmethyl ester; Enantio selective hydrolysis; Glyceryl ester; Non protein amino acid; Optical resolution; Porcine pancreatic lipase

Indexed keywords

CARBAMOYLMETHYL ESTER; ENANTIOSELECTIVE HYDROLYSIS; NON-PROTEIN AMINO ACID ESTERS;

ACETONITRILE; AMINO ACIDS; ENANTIOMERS; HYDROLYSIS; OPTICAL PROPERTIES; PHOSPHATES;

ESTERS;

ALIPHATIC AMINE; AROMATIC AMINO ACID; CARBAMOYLMETHYL ESTER; ESTER; FENCLONINE; GLYCERYL ESTER; PHENYLALANINE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HYDROLYSIS; HYDROPHILICITY; OPTICAL RESOLUTION; REACTION TIME;

SUS;

EID: 42049102423     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420701568641     Document Type: Article

References (30)

1. Albertson, NF (1946) Synthesis of amino acids from ethyl acetamidomalonate and ethyl acetamidocyanoacetate. III. Use of primary halides. J Am Chem Soc, 68, pp. 450-453.
2. Bautista, FM, Campelo, JM, Garcia, A., Luna, D. and Marinas, JM (1992) Porcine pancreatic lipase-catalyzed enantioselective hydrolysis of N-protected amino acid methyl esters. Amino Acids, 2, pp. 87-95.
3. Bergmann, M. and Zervas, L. (1932) Über ein all-gemeines Verfahren der Peptid-Synthese. Ber Deutsch Chem Gesellsch B, 65, pp. 1192-1201.
4. Brady, L., Brzozowski, AM, Derewenda, ZS, Dodson, E., Dodson, G., Tolley, S., Turkenburg, JP, Christiansen, L., Huge-Jensen, B., Norskov, L., Thim, L. and Menge, U. (1990) A serine protease triad forms the catalytic centre of a triacylglycerol lipase. Nature, 343, pp. 767-770.
5. Broos, J., Engbersen, JFJ, Sakodinskaya, IK, Verboom, W. and Reinhoudt, DN (1995) Activity and enantioselectivity of serine proteases in transesterification reactions in organic media. J Chem Soc, Perkin Trans, 1, pp. 2899-2905.
6. Brzozowski, AM, Derewenda, U., Derewenda, ZS, Dodson, GG, Lawson, DM, Turkenburg, JP, Bjorkling, F., Huge-Jensen, B., Patkar, SA and Thim, L. (1991) A model for interfacial activation in lipases from the structure of a fungal lipase-inhibitor complex. Nature, 351, pp. 491-494.
7. Capellas, M., Benaiges, MD, Caminal, G., Gonzalez, G., Lopez-Santin, J. and Clapes, P. (1996) Enzymic synthesis of a CCK-8 tripeptide fragment in organic media. Biotechnol Bioeng, 50, pp. 700-708.
8. Chen, C-S, Fujimoto, Y., Girdaukas, G. and Sih, CJ (1982) Quantitative analyses of biochemical kinetic resolution of enantiomers. J Am Chem Soc, 104, pp. 7294-7299.
9. Gomori, G. (1955) Preparation of buffers for use in enzyme studies. Methods Enzymol, 1, pp. 138-146.
10. Grochulski, P., Li, Y., Schrag, JD, Bouthillier, F., Smith, P., Harrison, D., Rubin, B. and Cygler, M. (1993) Insights into interfacial activation from an open structure of Candida rugosa lipase. J Biol Chem, 268, pp. 12843-12847.
11. Hermoso, J., Pignol, D., Kerfelec, B., Crenon, I., Chapus, C. and Fontecilla-Camps, JC (1996) Lipase activation by nonionic detergents. J Biol Chem, 271, pp. 18007-18016.
12. Houng, J-Y, Wu, M-L and Chen, S-T (1996) Kinetic resolution of amino acid esters catalyzed by lipases. Chirality, 8, pp. 418-422.
13. Kawashiro, K., Kaiso, K., Minato, D., Sugiyama, S. and Hayashi, H. (1993) Lipase-catalyzed peptide synthesis using Z-amino acid esters as acyl donors in aqueous water-miscible organic solvents. Tetrahedron, 49, pp. 4541-4548.
14. Kawashiro, K., Sugahara, H., Sugiyama, S. and Hayashi, H. (1995) Effect of water content on the enantioselectivity of α-chymotrypsin catalysis in organic media. Biotechnol Lett, 17, pp. 1161-1166.
15. Kawashiro, K., Sugahara, H., Tsukioka, T., Sugiyama, S. and Hayashi, H. (1996) Effect of ester moiety of substrates on enantioselectivity of protease catalysis in organic media. Biotechnol Lett, 18, pp. 1381-1386.
16. Kuhl, P., Zacharias, U., Burckhardt, H. and Jakubke, H-D (1986) On the use of carboxamidomethyl esters in the protease-catalyzed peptide synthesis. Monatshefte Chem, 117, pp. 1195-1204.
17. Maruyama, T., Nakajima, M., Kondo, H., Kawasaki, K., Seki, M. and Goto, M. (2003) Can lipases hydrolyze a peptide bond?. Enzyme Microb Technol, 32, pp. 655-657.
18. Mitin, YV, Braun, K. and Kuhl, P. (1997) Papain catalyzed synthesis of glyceryl esters of N-protected amino acids and peptides for use in trypsin catalyzed peptide synthesis. Biotechnol Bioeng, 54, pp. 287-290.
19. Miyazawa, T., Takitani, T., Ueji, S., Yamada, T. and Kuwata, S. (1988) Optical resolution of unusual amino acids by lipase-catalyzed hydrolysis. J Chem Soc, Chem Commun, pp. 1214-1215.
20. Miyazawa, T., Iwanaga, H., Ueji, S., Yamada, T. and Kuwata, S. (1989) Porcine pancreatic lipase catalyzed enantioselective hydrolysis of esters of N-protected unusual amino acids. Chem Lett, pp. 2219-2222.
21. Miyazawa, T., Iwanaga, H., Yamada, T. and Kuwata, S. (1992) Optical resolution of unusual amino acids using microbial proteases. Chirality, 4, pp. 427-431.
22. Miyazawa, T., Tanaka, K., Ensatsu, E., Yanagihara, R. and Yamada, T. (1998) Remarkable effects of donor esters on the α-chymotrypsin-catalyzed coupling of inherently poor amino acid substrates. Tetrahedr Lett, 39, pp. 997-1000.
23. Miyazawa, T., Iwanaga, H., Ueji, S. and Yamada, T. (2000) Optical resolution of non-protein amino acids by lipase-catalyzed ester hydrolysis. Biocatal Biotransform, 17, pp. 445-458.
24. Miyazawa, T., Tanaka, K., Ensatsu, E., Yanagihara, R. and Yamada, T. (2001) Broadening of the substrate tolerance of α-chymotrypsin by using the carbamoylmethyl ester as an acyl donor in kinetically controlled peptide synthesis. J Chem Soc, Perkin Trans, 1, pp. 87-94.
25. Miyazawa, T., Ensatsu, E., Yabuuchi, N., Yanagihara, R. and Yamada, T. (2002) Superiority of the carbamoylmethyl ester as an acyl donor for the kinetically controlled amide-bond formation mediated by α-chymotrypsin. J Chem Soc, Perkin Trans, 1, pp. 390-395.
26. Morán, C., Infante, MR and Clapés, P. (2001) Synthesis of glycero amino acid-based surfactants. Part 1. Enzymatic preparation of rac-1-O-(Nα-acetyl--aminoacyl)glycerol derivatives. J Chem Soc, Perkin Trans, 1, pp. 2063-2070.
27. Salam, SMA, Kagawa, K. and Kawashiro, K. (2005) α-Chymotrypsin-catalyzed peptide synthesis using N-protected-amino acid carbamoylmethyl esters as acyl donors. Biotechnol Lett, 27, pp. 1199-1203.
28. Salam, SMA, Kagawa, K. and Kawashiro, K. (2006) α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors. Tetrahedr: Asymm, 17, pp. 22-29.
29. So, J-E, Kang, S-H and Kim, B-G (1998) Lipase-catalyzed synthesis of peptides containing-amino acid. Enzyme Microb Technol, 23, pp. 211-215.
30. Wiese, J., Gattner, HG and Zahn, H. (1991) Use of Z-amino acid glyceryl esters in protease catalyzed peptide synthesis. Biomed Biochim Acta, 50, pp. 90-93.