Reviews

Application of Hydrolase Catalytic Promiscuity in Organic Synthesis

  • Ge Xin ,
  • Lai Yifeng ,
  • Chen Xinzhi
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  • a Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, Hangzhou 310027;
    b Zhejiang University of Science and Technology, School of Biological and Chemical Engineering, Hangzhou 310012

Received date: 2013-01-04

  Revised date: 2013-02-04

  Online published: 2013-02-18

Supported by

Project supported by the Key Innovation Group of Zhejiang Province (No. 2009R50002).

Abstract

This review introduces the mechanism of hydrolase promiscuity. Several applications of hydrolase catalytic promiscuity in unit reaction, two-step reaction and three-component reaction are summarized, especially for addition, aldol reaction, and Knoevenagel reaction.

Cite this article

Ge Xin , Lai Yifeng , Chen Xinzhi . Application of Hydrolase Catalytic Promiscuity in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1686 -1696 . DOI: 10.6023/cjoc201212048

References

[1] (a) Copley, S. D. Curr. Opin. Chem. Biol. 2003, 7(2), 265.
(b) Kazlauskas, R. J. Curr. Opin. Chem. Biol. 2005, 9(2), 195.
(c) Khersonsky, O.; Roodveldt, C.; Tawfik, D. S. Curr. Opin. Chem. Biol. 2006, 10(5), 498.
(d) Hult, K.; Berglund, P. Trends Biotechnol. 2007, 25(5), 231.
(e) Xu, J. M.; Lin, X. F. Chin. J. Org. Chem. 2007, 27(12), 1473 (in Chinese)
(许建明, 林贤福, 有机化学, 2007, 27(12), 1473.)
(f) Babtie, A.; Tokuriki, N.; Hollfelder, F. Curr. Opin. Chem. Biol. 2010, 14(2), 200.
[2] Nam, H.; Lewis, N. E.; Lerman, J. A.; Lee, D. H.; Chang, R. L.; Kim, D.; Palsson, B. O. Science 2012, 337(6098), 1101.
[3] Carlqvist, P.; Svedendahl, M.; Branneby, C.; Hult, K.; Brinck, T.; Berglund, P. ChemBioChem 2005, 6(2), 331.
[4] (a) Branneby, C.; Carlqvist, P.; Magnusson, A.; Hult, K.; Brinck, T.; Berglund, P. J. Am. Chem. Soc. 2003, 125(4), 874.
(b) Svedendahl, M.; Hult, K.; Berglund, P. J. Am. Chem. Soc. 2005, 127(51), 17988.
[5] Svedendahl, M.; Jovanovic, B.; Fransson, L.; Berglund, P. ChemCatChem 2009, 1(2), 252.
[6] Kitazume, T.; Ikeya, T.; Murata, K. J. Chem. Soc., Chem. Commun. 1986, (17), 1331.
[7] Cai, Y.; Yao, S. P.; Wu, Q.; Lin, X. F. Biotechnol. Lett. 2004, 26(6), 525.
[8] de Souza, R.; Matos, L. M. C.; Goncalves, K. M.; Costa, I. C. R.; Babics, I.; Leite, S. G. F.; Oestreicher, E. G.; Antunes, O. A. C. Tetrahedron Lett. 2009, 50(17), 2017.
[9] Xu, J. M.; Zhang, F.; Wu, Q.; Zhang, Q. Y.; Lin, X. F. J. Mol. Catal., B: Enzym. 2007, 49(1~4), 50.
[10] Strohmeier, G. A.; Sovic, T.; Steinkellner, G.; Hartner, F. S.; Andryushkova, A.; Purkarthofer, T.; Glieder, A.; Gruber, K.; Griengl, H. Tetrahedron 2009, 65(29~30), 5663.
[11] Li, C.; Feng, X. W.; Wang, N.; Zhou, Y. J.; Yu, X. Q. Green Chem. 2008, 10(6), 616.
[12] Li, C.; Zhou, Y. J.; Wang, N.; Feng, X. W.; Li, K.; Yu, X. Q. J. Biotechnol. 2010, 150(4), 539.
[13] Li, H. H.; He, Y. H.; Guan, Z. Catal. Commun. 2011, 12(7), 580.
[14] Xie, B. H.; Li, W.; Liu, Y.; Li, H. H.; Guan, Z.; He, Y. H. Tetrahedron 2012, 68(15), 3160.
[15] He, Y. H.; Li, H. H.; Chen, Y. L.; Xue, Y.; Yuan, Y.; Guan, Z. Adv. Synth. Catal. 2012, 354(4), 712.
[16] Lai, Y. F.; Zheng, H.; Chai, S. J.; Zhang, P. F.; Chen, X. Z. Green Chem. 2010, 12(11), 1917.
[17] Hu, W.; Guan, Z.; Deng, X.; He, Y. H. Biochimie 2012, 94(3), 656.
[18] Tang, R. C.; Guan, Z.; He, Y. H.; Zhu, W. J. Mol. Catal, B: Enzym. 2010, 63(1~2), 62.
[19] Wang, J. L.; Li, X.; Xie, H. Y.; Liu, B. K.; Lin, X. F. J. Biotechnol. 2010, 145(3), 240.
[20] Zaks, A.; Klibanov, A. M. Science 1984, 224(4654), 1249.
[21] Zaks, A.; Klibanov, A. M. J. Biol. Chem. 1988, 263(17), 8017.
[22] Cai, Y.; Wu, Q.; Xiao, Y. M.; Lv, D. S.; Lin, X. F. J. Biotechnol. 2006, 121(3), 330.
[23] Xu, J. M.; Zhang, F.; Liu, B. K.; Wu, Q.; Lin, X. F. Chem. Commun. 2007, (20), 2078.
[24] Wang, J. L.; Xu, J. M.; Wu, Q.; Lv, D. S.; Lin, X. F. Tetrahedron 2009, 65(12), 2531.
[25] (a) Wu, W. B.; Xu, J. M.; Wu, Q.; Lv, D. S.; Lin, X. F. Synlett 2005, (16), 2433.
(b) Wu, W. B.; Xu, J. M.; Wu, Q.; Lv, D. S.; Lin, X. F. Adv. Synth. Catal. 2006, 348(4~5), 4872.
[26] Torre, O.; Alfonso, I.; Gotor, V. Chem. Commun. 2004, (15), 1724.
[27] Madalinska, L.; Kwiatkowska, M.; Cierpial, T.; Kielbasinski, P. J. Mol. Catal., B: Enzym. 2012, 81, 25.
[28] Branneby, C.; Carlqvist, P.; Hult, K.; Brinck, T.; Berglund, P., J. Mol. Catal., B: Enzym. 2004, 31(4~6), 123.
[29] Guan, Z.; Fu, J. P.; He, Y. H. Tetrahedron Lett. 2012, 53 (37), 4959.
[30] Chen, X. A.; Liu, B. K.; Kang, H.; Lin, X. F. J. Mol. Catal., B: Enzym. 2011, 68(1), 71.
[31] Wang, C. H.; Guan, Z.; He, Y. H. Green Chem. 2011, 13(8), 2048.
[32] Xie, B. H.; Guan, Z.; He, Y. H. Biocatal. Biotransfor 2012, 30(2), 238.
[33] He, Y. H.; Hu, W.; Guan, Z. J. Org. Chem. 2012, 77(1), 200.
[34] Feng, X. W.; Li, C.; Wang, N.; Li, K.; Zhang, W. W.; Wang, Z.; Yu, X. Q. Green Chem. 2009, 11(12), 1933.
[35] Majumder, A. B.; Ramesh, N. G.; Gupta, M. N. Tetrahedron Lett. 2009, 50(37), 5190.
[36] Yao, S. P.; Lu, D. S.; Wu, Q.; Cai, Y.; Xu, S. H.; Lin, X. F. Chem. Commun. 2004, (17), 20067.
[37] Wu, M. Y.; Li, K.; He, T.; Feng, X. W.; Wang, N.; Wang, X. Y.; Yu, X. Q. Tetrahedron 2011, 67(14), 2681.
[38] Chai, S. J.; Lai, Y. F.; Xu, J. C.; Zheng, H.; Zhu, Q.; Zhang, P. F. Adv. Synth. Catal. 2011, 353(2~3), 371.
[39] Xu, J. C.; Li, W. M.; Zheng, H.; Lai, Y. F.; Zhang, P. F. Tetrahedron 2011, 67(49), 9582.
[40] Li, K.; He, T.; Li, C.; Feng, X. W.; Wang, N.; Yu, X. Q. Green Chem. 2009, 11(6), 777.
[41] He, T.; Li, K.; Wu, M. Y.; Feng, X. W.; Wang, N.; Wang, H. Y.; Li, C.; Yu, X. Q. J. Mol. Catal., B: Enzym. 2010, 67(3~4), 189.
[42] Chai, S. J.; Lai, Y. F.; Zheng, H.; Zhang, P. F. Helv. Chim. Acta 2010, 93(11), 2231.
[43] Xue, Y.; Li, L. P.; He, Y. H.; Guan, Z. Sci. Rreports 2012, 2.
[44] Wang, J. L.; Liu, B. K.; Yin, C.; Wu, Q.; Lin, X. F. Tetrahedron 2011, 6(14), 2689.
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