Abstract
Esterase BioH, which is obligatory for biotin synthesis in Escherichia coli, was found to exhibit a promiscuous ability to catalyse Aldol and Knoevenagel reactions with moderate to good yields. The reaction conditions including organic solvent, molar ratio of ketone to aldehyde, enzyme amount, and reaction time were investigated to evaluate the effect of different reaction conditions on yield. Target compounds were afforded in the best yield of 91.2% for Aldol reaction and 54.7% for Knoevenagel reaction. In addition, because the enzyme could be prepared with a low cost, this protocol could provide an economic route to conduct Aldol and Knoevenagel reactions, which expand the field of enzymatic promiscuity.
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References
Koeller K. M., Wong C. H., Nature, 2001, 409, 232
Jiang X. J., Hu Y., Jiang L., Gong J. H., Huang H., Chem. Res. Chinese Universities, 2013, 29(2), 223
Bornscheuer U. T., Kazlauskas R. J., Angew. Chem. Int. Ed., 2004, 43, 6032
Svedendahl M., Hult K., Berglund P., J. Am. Chem. Soc., 2005, 127, 17988
Wu W. B., Wang N., Xu J. M., Wu Q., Lin X. F., Chem. Commun., 2005, (18), 2348
Li K., He T., Li C., Feng X. W., Wang N., Yu X. Q., Green Chem., 2009, 11, 777
Reetz M. T., Mondiere R., Carballeira J. D., Tetrahedron Lett., 2007, 48, 1679
Tang R. C., Guan Z., He Y. H., Zhu W., J. Mol. Catal. B: Enzym., 2010, 63, 62
Wurtz A., Bull. Soc. Chim. Fr., 1872, 17, 436
Knoevenagel E., Ber. Dtsch. Chem. Ges., 1894, 27, 2345
Li C., Feng X. W., Wang N., Zhou Y. J., Yu X. Q., Green Chem., 2008, 10, 616
López-Iglesias M., Busto E., Gotor V., Gotor-Fernándes V., Adv. Synth. Catal., 2011, 353, 2345
Li H. H., He Y. H., Yuan Y., Guan Z., Green Chem., 2011, 13, 185
Hu W., Guan Z., Deng X., He Y. H., Biochimie, 2012, 94, 656
Wang B., Liu J., Tang X. L., Cheng C., Gu J. L., Dai L. Y., Yu H. W., Tetrahedron Lett., 2010, 51, 309
Wang B., Tang X. L., Liu J., Yu H. W., Tetrahedron Lett., 2010, 51, 6360
Tang X. L., Liu J., Wang B., Yu H. W., World J. Microbiol. Biotechnol., 2011, 27, 129
Zhang Y., Wang M. G., Liang J., Shang Z. C., Lett. Org. Chem., 2010, 7, 27
Martínez-Castañeda Á., Rodríguez-Solla H., Concellón C., Amo V. D., J. Org. Chem., 2012, 77, 10375
Li Z. N., Chen X. L., Fu Y. J., Wang W., Luo M., Res. Chem. Intermed., 2012, 38, 25
Yadav J. S., Bhunia D. C., Singh V. K., Srihari P., Tetrahedron Lett., 2009, 50, 2470
Liu R. D., Zhang J., Eur. J. Chem., 2011, 2, 308
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Supported by the National Natural Science Foundation of China(No.21176215).
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Jiang, L., Yu, H. Enzymatic promiscuity: Escherichia coli BioH esterase-catalysed Aldol reaction and Knoevenagel reaction. Chem. Res. Chin. Univ. 30, 289–292 (2014). https://doi.org/10.1007/s40242-014-3401-y
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DOI: https://doi.org/10.1007/s40242-014-3401-y