Resolution of non-protein amino acids via Carica papaya lipase-catalyzed enantioselective transesterification

Tetrahedron Asymmetry

Volumn 16, Issue 15, 2005, Pages 2569-2573

  Miyazawa, Toshifumi ^a   Onishi, Kazuki ^a   Murashima, Takashi ^a   Yamada, Takashi ^a   Tsai, Shau Wei ^b  

^a KONAN UNIVERSITY   (Japan)

^b NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CARICA PAPAYA EXTRACT; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; HYDROLYSIS; PAPAYA; PRIORITY JOURNAL; PROTEIN ANALYSIS; TRANSESTERIFICATION;

EID: 23644454974     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.06.037     Document Type: Article

References (32)

1. H.J. Gais, and F. Theil K. Drauz H. Waldmann Enzyme Catalysis in Organic Synthesis 2002 Wiley-VHC Weinheim 335 578
2. K. Faber Biotransformations in Organic Chemistry 4th ed. 2000 Springer Berlin pp 94-123, 344-367
3. U.T. Bornscheuer, and R.J. Kazlauskas Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations 1999 Wiley-VHC Weinheim pp 65-129
4. M. Baumann, B.H. Hauer, and U.T. Bornscheuer Tetrahedron: Asymmetry 11 2000 4781 4790
5. F. Cardenas, M.S. de Castro, J.M. Sanchez-Montero, J.V. Sinisterra, M. Valmaseda, S.W. Elson, and E. Alvarez Enzyme Microb. Technol. 28 2001 145 154
6. K.N. Kilcawley, M.G. Wilkinson, and P.F. Fox Enzyme Microb. Technol. 31 2002 310 320
7. L. Steenkamp, and D. Brady Enzyme Microb. Technol. 32 2003 472 477
8. P. Villeneuve Eur. J. Lipid Sci. Technol. 105 2003 308 317
9. C. Dhuique-Mayer, Y. Caro, M. Pina, J. Ruales, M. Dornier, and J. Graille Biotechnol. Lett. 23 2001 1021 1024
10. C. Palocci, S. Soro, E. Cerica, F. Fiorillo, C.M.A. Belsito, B. Monacelli, D. Monache, and G. Pasqua Plant Sci. 165 2003 577 582
11. Y.-C. Cheng, and S.-W. Tsai Tetrahedron: Asymmetry 15 2004 2917 2920
12. I.J. Colton, S.N. Ahmed, and R.J. Kazlauskas J. Org. Chem. 60 1995 212 217
13. J.J. Lalonde, C. Govardhan, N. Khalaf, A.G. Martinez, K. Visuri, and A.L. Margolin J. Am. Chem. Soc. 117 1995 6845 6852
14. C.-C. Chen, and S.-W. Tsai Enzyme Microb. Technol. 36 2005 127 132
15. I.-S. Ng, and S.-W. Tsai Biotechnol. Bioeng. 89 2005 88 95
16. D.C. Roberts, and F. Vellaccio Unusual Amino Acids in Peptide Synthesis E. Gross J. Meienhofer The Peptides Vo1. 5 1983 Academic Press New York 341 449
17. G.M. Coppola, and H.F. Schuster Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids 1987 John Wiley New York
18. T. Miyazawa, H. Iwanaga, S. Ueji, and T. Yamada Biocatal. Biotrans. 17 2000 445 458
19. T. Miyazawa, M. Mio, Y. Watanabe, T. Yamada, and S. Kuwata Biotechnol. Lett. 14 1992 789 794
20. R.S. Phillips Trends Biotechnol. 14 1996 13 16
21. C.-S. Chen, Y. Fujimoto, G. Girdukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299
22. A small amount (0.2% yield) of the d-methyl ester d-2d was detected after 24 h.
23. K. Faber Biotransformations in Organic Chemistry 4th ed. 2000 Springer Berlin p 42
24. In the transesterification with ethanol, the d-ethyl ester was not detected after 24 h. Taking into account the limit of detection on HPLC, the % ee value of the newly formed ethyl ester was estimated to be >99.8 as shown in Table 1.
25. A.M.P. Koskinen A.M. Klibanov Enzymatic Reactions in Organic Media 1996 Blackie A&P Glasgow
26. T. Miyazawa, H. Minowa, K. Imagawa, and T. Yamada Chromatographia 60 2004 45 50
27. T. Miyazawa, Y. Shindo, and T. Yamada Chromatographia 60 2004 419 424
28. In the case of amino acids bearing aromatic side chains, high enantioselectivities have not been obtained so far, because the use of such a solvent with higher polarity as isopropyl ether is inevitable due to the lower solubilities in cyclohexane of the substrates derived from the amino acids.
29. J.P. Greenstein, and M. Winitz Chemistry of the Amino Acids Vol. 3 1961 John Wiley New York pp 2384-2387
30. M. Bodanszky, and A. Bodanszky The Practice of Peptide Synthesis 1984 Springer Berlin pp 12-15
31. M.K. Dhaon, R.K. Olsen, and K. Ramasamy J. Org. Chem. 47 1982 1962 1965
32. For compound 1a, see: T. Miyazawa, K. Tanaka, E. Ensatsu, R. Yanagihara, and T. Yamada J. Chem. Soc., Perkin Trans. 1 2001 87 93