Recent developments in enzyme promiscuity for carbon-carbon bond-forming reactions

Current Opinion in Chemical Biology

Volumn 25, Issue , 2015, Pages 115-123

  Miao, Yufeng ^a   Rahimi, Mehran ^a   Geertsema, Edzard M ^a   Poelarends, Gerrit J ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ENZYME;

ALDOL REACTION; BIOCATALYST; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HENRY REACTION; KNOEVENAGEL CONDENSATION; MANNICH REACTION; MICHAEL ADDITION; REVIEW; SYNTHESIS; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM;

CARBON; ENZYMES; SUBSTRATE SPECIFICITY;

EID: 84920937701     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2014.12.020     Document Type: Review

References (51)

1. Hult K., Berglund P. Enzyme promiscuity: mechanism and applications. Trends Biotechnol 2007, 25:231-238.
2. Khersonsky O., Roodveldt C., Tawfik D.S. Enzyme promiscuity: evolutionary and mechanistic aspects. Curr Opin Chem Biol 2006, 10:498-508.
3. Humble M.S., Berglund P. Biocatalytic promiscuity. Eur J Org Chem 2011, 2011:3391-3401.
4. Baas B.J., Zandvoort E., Geertsema E.M., Poelarends G.J. Recent advances in the study of enzyme promiscuity in the tautomerase superfamily. ChemBioChem 2013, 14:917-926.
5. Khersonsky O., Tawfik D.S. Enzyme promiscuity: a mechanistic and evolutionary perspective. Annu Rev Biochem 2010, 79:471-505.
6. Resch V., Schrittwieser J.H., Siirola E., Kroutil W. Novel carbon-carbon bond formations for biocatalysis. Curr Opin Biotechnol 2011, 22:793-799.
7. Fesko K., Gruber-Khadjawi M. Biocatalytic methods for CC bond formation. ChemCatChem 2013, 5:1248-1272.
8. Milner S.E., Moody T.S., Maguire A.R. Biocatalytic approaches to the Henry (nitroaldol) reaction. Eur J Org Chem 2012, 2012:3059-3067.
9. Müller M. Recent developments in enzymatic asymmetric CC bond formation. Adv Synth Catal 2012, 354:3161-3174.
10. Ding Y., Huang H., Hu Y. New progress on lipases catalyzed CC bond formation reactions. Chin J Org Chem 2013, 33:905-914.
11. Branneby C., Carlqvist P., Magnusson A., Hult K., Brinck T., Berglund P. Carbon-carbon bonds by hydrolytic enzymes. J Am Chem Soc 2003, 125:874-875.
12. Li C., Feng X.W., Wang N., Zhou Y.J., Yu X.Q. Biocatalytic promiscuity: the first lipase-catalysed asymmetric aldol reaction. Green Chem 2008, 10:616-618.
13. Li C., Zhou Y.J., Wang N., Feng X.W., Li K., Yu X.Q. Promiscuous protease-catalyzed aldol reactions: a facile biocatalytic protocol for carbon-carbon bond formation in aqueous media. J Biotechnol 2010, 150:539-545.
14. Wang N., Zhang W., Zhou L.H., Deng Q.F., Xie Z.B., Yu X.Q. One-pot lipase-catalyzed aldol reaction combination of in situ formed acetaldehyde. Appl Biochem Biotechnol 2013, 171:1559-1567.
15. Zandvoort E., Baas B.J., Quax W.J., Poelarends G.J. Systematic screening for catalytic promiscuity in 4-oxalocrotonate tautomerase: enamine formation and aldolase activity. ChemBioChem 2011, 12:602-609.
16. Zandvoort E., Geertsema E.M., Quax W.J., Poelarends G.J. Enhancement of the promiscuous aldolase and dehydration activities of 4-oxalocrotonate tautomerase by protein engineering. ChemBioChem 2012, 13:1274-1277.
17. Guan Z., Fu J.P., He Y.H. Biocatalytic promiscuity: lipase-catalyzed asymmetric aldol reaction of heterocyclic ketones with aldehydes. Tetrahedron Lett 2012, 53:4959-4961.
18. Li H.H., He Y.H., Yuan Y., Guan Z. Nuclease p1: a new biocatalyst for direct asymmetric aldol reaction under solvent-free conditions. Green Chem 2011, 13:185-189.
19. Li H.H., He Y.H., Guan Z. Protease-catalyzed direct aldol reaction. Catal Commun 2011, 12:580-582.
20. He Y.H., Li H.H., Chen Y.L., Xue Y., Yuan Y., Guan Z. Chymopapain-catalyzed direct asymmetric aldol reaction. Adv Synth Catal 2012, 354:712-719.
21. Xie B.H., Li W., Liu Y., Li H.H., Guan Z., He Y.H. The enzymatic asymmetric aldol reaction using acidic protease from Aspergillus usamii. Tetrahedron 2012, 68:3160-3164.
22. Yuan Y., Guan Z., He Y.H. Biocatalytic direct asymmetric aldol reaction using proteinase from Aspergillus melleus. Sci China Chem 2013, 56:939-944.
23. Chen Y.L., Li W., Liu Y., Guan Z., He Y.H. Trypsin-catalyzed direct asymmetric aldol reaction. J Mol Catal B Enzym 2013, 87:83-87.
24. Fu J.P., Gao N., Yang Y., Guan Z., He Y.H. Ficin-catalyzed asymmetric aldol reactions of heterocyclic ketones with aldehydes. J Mol Catal B Enzym 2013, 97:1-4.
25. Xie Z.B., Wang N., Jiang G.F., Yu X.Q. Biocatalytic asymmetric aldol reaction in buffer solution. Tetrahedron Lett 2013, 54:945-948.
26. Xie Z.B., Wang N., Zhou L.H., Wan F., He T., Le Z.G., Yu X.Q. Lipase-catalyzed stereoselective cross-aldol reaction promoted by water. ChemCatChem 2013, 5:1935-1940.
27. Geertsema E.M., Poelarends G.J. Enzymatic carbon-carbon bond-forming Michael-type additions. Thieme Chemistry 2014, vol 2. Stuttgart, Germany. K. Faber, W.D. Fessner, N. Turner (Eds.).
28. Lee R.S. The Michael addition reactions of aromatic 2-nitroethenes with β-dicarbonyl compounds catalyzed by lipase. Huaxue (The Chinese Chemical Society) 1996, 54:23-27.
29. Svedendahl M., Hult K., Berglund P. Fast carbon-carbon bond formation by a promiscuous lipase. J Am Chem Soc 2005, 127:17988-17989.
30. Svedendahl M., Jovanović B., Fransson L., Berglund P. Suppressed native hydrolytic activity of a lipase to reveal promiscuous Michael addition activity in water. ChemCatChem 2009, 1:252-258.
31. Cai J.F., Guan Z., He Y.H. The lipase-catalyzed asymmetric CC Michael addition. J Mol Catal B Enzym 2011, 68:240-244.
32. Xie B.H., Guan Z., He Y.H. Promiscuous enzyme-catalyzed Michael addition: synthesis of warfarin and derivatives. J Chem Technol Biotechnol 2012, 87:1709-1714.
33. Zandvoort E., Geertsema E.M., Baas B.J., Quax W.J., Poelarends G.J. Bridging between organocatalysis and biocatalysis: asymmetric addition of acetaldehyde to β-nitrostyrenes catalyzed by a promiscuous proline-based tautomerase. Angew Chem Int Ed 2012, 51:1240-1243.
34. Miao Y., Geertsema E.M., Tepper P.G., Zandvoort E., Poelarends G.J. Promiscuous catalysis of asymmetric Michael-type additions of linear aldehydes to β-nitrostyrene by the proline-based enzyme 4-oxalocrotonate tautomerase. ChemBioChem 2013, 14:191-194.
35. Geertsema E.M., Miao Y., Tepper P.G., de Haan P., Zandvoort E., Poelarends G.J. Biocatalytic Michael-type additions of acetaldehyde to nitroolefins with the proline-based enzyme 4-oxalocrotonate tautomerase yielding enantioenriched γ-nitroaldehydes. Chem Eur J 2013, 19:14407-14410.
36. Geertsema E.M., Miao Y., Poelarends G.J. Asymmetric Michael-type additions of acetaldehyde to nitroolefins catalyzed by 4-oxalocrotonate tautomerase (4-OT) yielding valuable γ-nitroaldehydes. Practical Methods in Biocatalysis and Biotransformations 2014, vol 3. Wiley, (in press).
37. Narancic T., Radivojevic J., Jovanovic P., Francuski D., Bigovic M., Maslak V., Savic V., Vasiljevic B., O'Connor K.E., Nikodinovic-Runic J. Highly efficient Michael-type addition of acetaldehyde to β-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. Bioresour Technol 2013, 142:462-468.
38. Li K., He T., Li C., Feng X.W., Wang N., Yu X.Q. Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for CC bond formation in a one-pot synthesis. Green Chem 2009, 11:777-779.
39. He T., Li K., Wu M.Y., Feng X.W., Wang N., Wang H.Y., Li C., Yu X.Q. Utilization of biocatalytic promiscuity for direct Mannich reaction. J Mol Catal B Enzym 2010, 67:189-194.
40. Chai S.J., Lai Y.F., Zheng H., Zhang P.F. A novel trypsin-catalyzed three-component Mannich reaction. Helv Chim Acta 2010, 93:2231-2236.
41. Xue Y., Li L.P., He Y.H., Guan Z. Protease-catalysed direct asymmetric Mannich reaction in organic solvent. Sci Rep 2012, 2:761-764.
42. Purkarthofer T., Gruber K., Gruber-Khadjawi M., Waich K., Skranc W., Mink D., Griengl H. A biocatalytic Henry reaction-the hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions. Angew Chem Int Ed 2006, 45:3454-3456.
43. Fuhshuku K., Asano Y. Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous-organic biphasic system. J Biotechnol 2011, 153:153-159.
44. Tang R.C., Guan Z., He Y.H., Zhu W. Enzyme-catalyzed Henry (nitroaldol) reaction. J Mol Catal B Enzym 2010, 63:62-67.
45. Xia W.J., Xie Z.B., Jiang G.F., Le Z.G. The Henry reaction in [Bmim][PF6]-based microemulsions promoted by acylase. Molecules 2013, 18:13910-13919.
46. Kühbeck D., Dhar B.B., Schön E.M., Cativiela C., Gotor-Fernández V., Díaz Díaz D. CC bond formation catalyzed by natural gelatin and collagen proteins. Beilstein J Org Chem 2013, 9:1111-1118.
47. Wang C.H., Guan Z., He Y.H. Biocatalytic domino reaction: synthesis of 2H-1-benzopyran-2-one derivatives using alkaline protease from Bacillus licheniformis. Green Chem 2011, 13:2048-2054.
48. Xie B.H., Guan Z., He Y.H. Biocatalytic Knoevenagel reaction using alkaline protease from Bacillus licheniformis. Biocatal Biotransform 2012, 30:238-244.
49. Lai Y.F., Zheng H., Chai S.J., Zhang P.F., Chen X.Z. Lipase-catalysed tandem Knoevenagel condensation and esterification with alcohol cosolvents. Green Chem 2010, 12:1917-1918.
50. Liu Z.Q., Xiang Z.W., Shen Z., Wu Q., Lin X.F. Enzymatic enantioselective aldol reactions of isatin derivatives with cyclic ketones under solvent-free conditions. Biochimie 2014, 101:156-160.
51. Gillingham D.G., Stallforth P., Adibekian A., Seeberger P.H., Hilvert D. Chemoenzymatic synthesis of differentially protected 3-deoxysugars. Nat Chem 2010, 2:102-105.