Bulletin of the Korean Chemical Society

  • 제33권2호
  • /
  • Pages.409-414
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  • 2012
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  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Lipase Catalyzed Kinetic Resolution of rac-2-(3-Methoxy-4-methylphenyl) propan-1-ol and rac-2-(3-Hydroxy-4-methylphenyl)propyl propanoate for S-(+)-Xanthorrhizol

  • 투고 : 2011.11.01
  • 심사 : 2011.11.23
  • 발행 : 2012.02.20
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초록

Xanthorrhizol is a bisabolane type of natural sesquiterpene, the major component of essential oils of Curcuma xanthorrhiza. 2-(3-Methoxy-4-methylphenyl)propan-1-ol and 2-(3-hydroxy-4-methyl phenyl)propan-1-ol could be essential building block for enantioselective synthesis of xanthorrhizol. Enantioselective (c = 53%, E = $80{\pm}3$) for R-(+)-2-(3-hydroxy-4-methylphenyl) propan-1-ol and (c = 58%, E = $27{\pm}1$) for R-(+)-2-(3-methoxy-4-methylphenyl) propan-1-ol resolution processes were developed via lipase-catalyzed reaction. We found lipase Aspergillus oryzae (AOL) and Porcine pancreas (PPL) are selective to transesterification and hydrolysis in organic and aqueous phase. Modified demethylated substrate is appropriate for enantioselective hydrolysis reaction without any additives. Enantiopure chiral alcohol was crystallized from ethyl acetate/n-hexane co-solvent system. Gram scale resolved chiral intermediate will facilitate the synthesis of the unnatural S-(+)-xanthorrhizol, the corresponding isomer of the natural one.

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참고문헌

  1. Rimpler, H.; Hansel, R.; Kochendoerfer, L. Z. Naturforsch Teil B 1970, 25(9), 995.
  2. John, T. K.; Krisna Rao, G. S. Indian. J. Chem. 1985, 24B(1), 35.
  3. Aguilar, M. I.; Delgado, G.; Bye, R.; Linares, E. Phytochemistry 1993, 33(5), 1161. https://doi.org/10.1016/0031-9422(93)85041-O
  4. Aggarwal, B. B.; Kumar, A.; Bharti, A. C. Anticancer Res. 2003, 23, 363.
  5. Pillai I, G. R.; Srivastava I, A. S.; Hassanein, T. I.; Chauhan, D. P.; Carrier, E. Cancer Lett. 2004, 208, 163. https://doi.org/10.1016/j.canlet.2004.01.008
  6. Hwang, J. K.; Shim, J. S.; Baek, N. I.; Pyun, Y. R. Planta Med. 2000, 66(2), 196. https://doi.org/10.1055/s-0029-1243135
  7. Choi, M. A.; Kim, S. H.; Chung, W. Y.; Hwang, J. K.; Park, K. K. Biochem. Biophys. Res. Commun. 2005, 326, 210. https://doi.org/10.1016/j.bbrc.2004.11.020
  8. Lim, C. S.; Jin, D. Q.; Mok, H.; Oh, S. J.; Lee, J. U.; Hwang, J. K.; Ha, I.; Han, J. S. J. Neurosci. Res. 2005, 82(6), 831. https://doi.org/10.1002/jnr.20692
  9. Montiel, L. E.; Zepeda, L. G.; Tamariz, J. Helv. Chim. Acta 2010, 93, 1261. https://doi.org/10.1002/hlca.201000111
  10. Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans 1 2000, 22, 3758.
  11. Sirat, H. M.; Hong, N. M.; Jauri, M. H. Tetrahedron Lett. 2007, 48, 457. https://doi.org/10.1016/j.tetlet.2006.11.051
  12. Barth, S.; Effenberger, F. Tetrahedron: Asymmetry 1993, 4, 823. https://doi.org/10.1016/S0957-4166(00)80120-2
  13. Goto, M.; Kawasaki, M.; Kometani, T. J. Mol. Catal. B: Enzym. 2000, 9, 245. https://doi.org/10.1016/S1381-1177(99)00101-0
  14. Hirose, K.; Naka, H.; Yano, M.; Ohashi, S.; Naemura, K.; Tobe, Y. Tetrahedron: Asymmetry 2000, 11, 1199. https://doi.org/10.1016/S0957-4166(00)00060-4
  15. Nordin, O.; Nguyen, B. V.; Vorde, C.; Hedenstrom, E.; Hogberg, H. E. J. Chem. Soc., Perkin Trans 1 2000, 367.
  16. Kazlauskas, R. J.; Bornscheuer, U. T. Biotechnology: Biotransformations I; Kelly, D. R., Ed.; Weinheim, Wiley-VCH: 1998; 2nd ed.; Vol. 8a, p 37.
  17. Serra, S. Tetrahedron: Asymmetry 2011, 22, 619. https://doi.org/10.1016/j.tetasy.2011.03.012
  18. Cheong, C. S.; Ku, I. H.; Kim, R. H.; Kim, U. J.; Ban, J. G. Repub. Korea 2009; p 20, Application: KR 2007-0108998.
  19. Straathof, A. J. J.; Jongejan, J. A. Enzyme Microb. Technol. 1997, 21, 559. https://doi.org/10.1016/S0141-0229(97)00066-5
  20. Bornscheuer, U. T.; Kazlauskas, R. J. Hydrolases in Organic Synthesis; Weinheim, Wiley-VCH: 1999; p 47.
  21. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294. https://doi.org/10.1021/ja00389a064
  22. Rakels, J. L. L.; Straathof, A. J. J.; Heijnen, J. J. A. Enzyme Microb. Technol. 1993, 15, 1051. https://doi.org/10.1016/0141-0229(93)90053-5