본문 바로가기
HOME> 논문 > 논문 검색상세

논문 상세정보

Bulletin of the Korean Chemical Society v.26 no.4, 2005년, pp.515 - 522   피인용횟수: 3

Dynamic Kinetic Resolutions and Asymmetric Transformations by Enzyme-Metal Combo Catalysis

Kim, Mahn-Joo    (National Research Laboratory of Chirotechnology and Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology   ); Ahn, Yang-Soo    (National Research Laboratory of chirotechnology and Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology   ); Park, Jai-Wook    (National Research Laboratory of chirotechnology and Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology  );
  • 초록

    Enzyme-metal combo catalysis is described as a useful methodology for the synthesis of optically active compounds. The key point of the method is the use of enzyme and metal in combination as the catalysts for the complete transformation of racemic substrates to single enantiomeric products through dynamic kinetic resolution (DKR). In this approach, enzyme acts as an enantioselective resolving catalyst and metal does as a racemizing catalyst for the efficient DKR. Three kinds of enzyme-metal combinations - lipase-ruthenium, subtilisin-ruthenium, and lipase-palladium ?have been developed as the catalysts for the DKRs of racemic alcohols, esters, and amines. The scope of the combination catalysts can be extended to the asymmetric transformations of ketones, enol acetates, and ketoximes via the DKRs. In most cases studied, enzyme-metal combo catalysis provided enantiomerically-enriched products in high yields.


  • 주제어

    Catalytic racemization .   Dynamic kinetic resolution .   Asymmetric transformation .   Enzyme-metal combo catalysis .   Chirotechnology.  

  • 참고문헌 (66)

    1. Sheldon, R. A. Chirotechnology, Industrial Synthesis of Optically Active Compounds; Dekker: New York, 1993 
    2. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, UK, 1994 
    3. Koskinen, A. M. P.;Klibanov, A. M. Enzymatic Reactions in Organic Media; Blackie Academic & Professional: Glasgow, Scotland, 1996 
    4. Faber, K. Biotransformations in Organic Chemistry, 3rd ed.; Springer: Berlin, Germany, 1997 
    5. Bornscheuer, U. T.; Kazlauskas, R. J. Hydrolases in Organic Synthesis; Wiley-VCH: Weiheim, Germany, 1999 
    6. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2002; Vols. I-III 
    7. Kim, M.-J.; Choi, G.-B.; Kim, J.-J.; Kim, H. J. Tetrahedron Lett. 1995, 36, 6253 
    8. Kim, M.-J.; Lim, I.-T.; Choi, G.-B.; Whang, S.-Y.; Ku, B.-C.; Choi, J.-Y. Bioorg. Med. Chem. Lett. 1996, 6, 71 
    9. Kim, M.-J.; Lim, I. T.; Kim, H.-J.; Wong, C.-H. Tetrahedron: Asymmetry 1997, 8, 1507 
    10. Lee, D.; Kim, M.-J. Tetrahedron Lett. 1998, 39, 2163 
    11. Lee, D.; Kim, M.-J. Tetrahedron Lett. 1998, 39, 9039 
    12. Lee, D.; Kim, M.-J. Org. Lett. 1999, 1, 925 
    13. Im, A. S.; Cheong, C. S.; Lee, S. H. Bull. Korean Chem. Soc. 2003, 24, 1269     
    14. Kang, H.-Y.; Ji, Y.; Yu, Y.-K.; Yu, J.-Y.; Lee, Y.; Lee, S.-J. Bull. Korean Chem. Soc. 2003, 24, 1819     
    15. Sturmer, R. Angew. Chem. Int. Ed. Engl. 1997, 36, 1173 
    16. El Gihani, M. T.; Williams, J. M. J. Curr. Opin. Biotechnol. 1999, 3, 11 
    17. Azerad, R.; Buisson, D. Curr. Opin. Biotechnol. 2000, 11, 565 
    18. Huerta, F. F.; Minidis, A. B. E.; Backvall, J.-E. Chem. Soc. Rev. 2001, 30, 321 
    19. Kim, M.-J.; Ahn, Y.; Park, J. Curr. Opin. Biotechnol. 2002, 13, 578 
    20. Pellissier, H. Tetrahedron 2003, 59, 8291 
    21. Pamies, O.; Backvall, J.-E. Chem. Rev. 2003, 103, 3247 
    22. Turner, N. J. Curr. Opin. Chem. Biol. 2004, 8, 114 
    23. Allen, J. V.; Williams, J. M. J. Tetrahedron Lett. 1996, 37, 1859 
    24. Dinh, P. M.; Howarth, J. A.; Hudnott, A. R.; Williams, J. M. J.; Harris, W. Tetrahedron Lett. 1996, 37, 7623 
    25. Reetz, M. T.; Schimossek, K. Chimia 1996, 50, 668 
    26. Choi, J. H.; Kim, Y. H.; Nam, S. H.; Shin, S. T.; Kim, M.-J.; Park, J. Angew. Chem. Int. Ed. Engl. 2002, 41, 2373 
    27. Larsson, A. L. E.; Persson, B. A.; Backvall, J.-E. Angew. Chem. Int. Ed. Engl. 1997, 36, 1211 
    28. Lee, H. K.; Ahn, Y. Bull. Korean Chem. Soc. 2004, 25, 1471     
    29. Koh, J. H.; Jeong, H. M.; Kim, M.-J.; Park, J. Tetrahedron Lett. 1999, 40, 6281 
    30. Lee, D.; Huh, E. A.; Kim, M.-J.; Jung, H. M.; Koh, J. H.; Park, J. Org. Lett. 2000, 2, 2377 
    31. Kim, K. W.; Song, B.; Choi, M. Y.; Kim, M.-J. Org. Lett. 2001, 3, 1507 
    32. Lee, J. K.; Kim, M.-J. J. Org. Chem. 2002, 67, 6845 
    33. Erbeldinger, M.; Mesiano, A. J.; Russel, A. Biotechnol. Prog. 2000, 16, 1129 
    34. Lau, R. M.; Rantwijk, F. van; Seddon, K. R.; Sheldon, R. A. Org. Lett. 2000, 2, 4189 
    35. Itoh, T.; Akasaki, E.; Kudo, K.; Shirakami, S. Chem. Lett. 2001, 262 
    36. Park, S.; Kazlauskas, R. J. Org. Chem. 2001, 66, 8395 
    37. Kim, M.-J.; Kim, H. M.; Kim, D.; Ahn, Y.; Park, J. Green Chem. 2004, 6, 471 
    38. Choi, J. H.; Choi, Y. K.; Kim, Y. H.; Park, E. S.; Kim, E. J.; Kim, M.-J.; Park, J. J. Org. Chem. 2004, 69, 1972 
    39. Csjernyik, G.; Bogar, K.; Backvall, J.-E. Tetrahedron Lett. 2004, 45, 6799 
    40. Martin-Matute, B.; Edin, M.; Bogar, K.; Backvall, J.-E. Angew. Chem. Int. Ed. 2004, 43, 6535 
    41. Dijksman, A.; Elzinga, J. M.; Li, Y. X.; Arends, W. C. E.; Sheldon, R. A. Tetrahedron: Asymmetry 2002, 13, 879 
    42. Edin, M.; Backvall, J.-E. J. Org. Chem. 2003, 68, 2216 
    43. Runmo, A. B. L.; Pamies, O.; Faber, K.; Backvall, J.- E. Tetrahedron Lett. 2002, 43, 2983 
    44. Pamies, O.; Backvall, J.- E. J. Org. Chem. 2002, 67, 1261 
    45. Pamies, O.; Backvall, J.-E. J. Org. Chem. 2001, 66, 4022 
    46. Kim, M.-J.; Choi, Y. K.; Choi, M. Y.; Kim, M.; Park, J. J. Org. Chem. 2001, 66, 4736 
    47. Pamies, O.; Backvall, J.-E. Adv. Synth. Catal. 2001, 343, 726 
    48. Pamies, O.; Backvall, J.-E. J. Org. Chem. 2002, 67, 9006 
    49. Pamies, O.; Backvall, J.-E. J. Org. Chem. 2003, 68, 4815 
    50. Kim, M.-J.; Chung, Y. I.; Choi, Y. K.; Lee, H. K.; Kim, D.; Park, J. J. Am. Chem. Soc. 2003, 125, 11494 
    51. Choi, Y. K.; Suh, J. H.; Lee, D.; Lim, I. T.; Jung, J. Y.; Kim, M.-J. J. Org. Chem. 1999, 64, 8423 
    52. Pamies, O.; Ell, A. H.; Samec, J. S. M.; Hermanns, N.; Backvall, J.-E. Tetrahedron Lett. 2002, 43, 4699 
    53. Jung, H. M.; Koh, J. H.; Kim, M.-J.; Park, J. Org. Lett. 2000, 2, 409 
    54. Jung, H. M.; Koh, J. H.; Kim, M.-J.; Park, J. Org. Lett. 2000, 2, 2487 
    55. Kim, M.-J.; Choi, M. Y.; Han, M. Y.; Choi, Y. K.; Lee, J. K.; Park, J. J. Org. Chem. 2002, 67, 9481 
    56. Choi, Y. K.; Kim, M.; Ahn, Y.; Kim, M.-J. Org. Lett. 2001, 3, 4099 
    57. Kim, W.-H.; Karvembu, R.; Park, J. Bull. Korean Chem. Soc. 2004, 25, 931     
    58. Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475 
    59. Schoefer, S. H.; Kraftzik, N.; Wasserscheid, P.; Kragl, U. Chem. Commun. 2001, 425 
    60. Kim, M.-J.; Lim, I.-T. Synlet 1996, 138 
    61. Pamies, O.; Backvall, J.-E. Curr. Opin. Biotechnol. 2003, 14, 407 
    62. Kim, M.-J.; Choi, M. Y.; Lee, J. K.; Ahn, Y. J. Mol. Catal. B.: Enzym. 2003, 26, 115 
    63. Chung, S.-K.; Chang, Y.-T.; Lee, E. J.; Shin, B.-G.; Kwon, Y.-U.; Kim, K.-C.; Lee, D. H.; Kim, M.-J. Bioorg. Med. Chem. Lett. 1998, 8, 1503 
    64. Persson, B. A.; Larsson, A. L. E.; Ray, M. L.; Backvall, J.-E. J. Am. Chem. Soc. 1999, 121, 1645 
    65. Persson, B. A.; Huerta, F. F.; Backvall, J.-E. J. Org. Chem. 1999, 64, 5237 
    66. Huerta, F. F.; Laxmi, S. Y. R.; Backvall, J.-E. Org. Lett. 2000, 2, 1037 
  • 이 논문을 인용한 문헌 (3)

    1. 2006. "" Bulletin of the Korean Chemical Society, 27(11): 1885~1887     
    2. 2007. "" Bulletin of the Korean Chemical Society, 28(11): 2096~2098     
    3. 2010. "" Bulletin of the Korean Chemical Society, 31(3): 650~652     

 활용도 분석

  • 상세보기

    amChart 영역
  • 원문보기

    amChart 영역

원문보기

무료다운로드
유료다운로드
  • 원문이 없습니다.

유료 다운로드의 경우 해당 사이트의 정책에 따라 신규 회원가입, 로그인, 유료 구매 등이 필요할 수 있습니다. 해당 사이트에서 발생하는 귀하의 모든 정보활동은 NDSL의 서비스 정책과 무관합니다.

원문복사신청을 하시면, 일부 해외 인쇄학술지의 경우 외국학술지지원센터(FRIC)에서
무료 원문복사 서비스를 제공합니다.

NDSL에서는 해당 원문을 복사서비스하고 있습니다. 위의 원문복사신청 또는 장바구니 담기를 통하여 원문복사서비스 이용이 가능합니다.

이 논문과 함께 출판된 논문 + 더보기