Hydrolase-catalyzed fast Henry reaction of nitroalkanes and aldehydes in organic media

Journal of Biotechnology

Volumn 145, Issue 3, 2010, Pages 240-243

  Wang, Jun Liang ^a   Li, Xia ^a   Xie, Hong Yan ^a   Liu, Bo Kai ^a   Lin, Xian Fu ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Nitroalkanols; Aldehyde; Henry reaction; Hydrolase; Nitroalkanes

Indexed keywords

D-AMINOACYLASE; ENZYME CONCENTRATIONS; FAST ADDITION; HENRY REACTIONS; HIGH YIELD; HYDROLASE; HYDROLASES; MOLAR RATIO; NITROALKANES; ORGANIC MEDIA; REACTION CONDITIONS;

ORGANIC SOLVENTS; PARAFFINS;

ALDEHYDES;

ALDEHYDE; AMINOACYLASE; DIMETHYL SULFOXIDE; HYDROLASE; NITROALKANE;

ARTICLE; ASPERGILLUS ORYZAE; CANDIDA; CANDIDA ANTARCTICA; CANDIDA CYLINDRACEA; CATALYSIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; ENZYME SUBSTRATE; ESCHERICHIA COLI; MUCOR; MUCOR JAVANICUS; MUCOR MEIHEI; NONHUMAN; PRIORITY JOURNAL; SOLVENT EFFECT; SWINE; TEMPERATURE;

ALDEHYDES; ALKANES; BENZALDEHYDES; BIOCATALYSIS; ETHANE; HYDROLASES; MODELS, CHEMICAL; NITRO COMPOUNDS; NITROPARAFFINS; SOLVENTS; SUBSTRATE SPECIFICITY;

EID: 73749083243     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2009.11.022     Document Type: Article

References (40)

1. Ballini R.J. New and convenient synthesis of (Z)-heneicos-6-en-11-one, the douglas fir tussock moth (Orgyia pseudotsugata) sex pheromone, and (Z)-non-6-en-2-one, the immediate precursor for the synthesis of brevicomin, the sex attractant of the western pine beetle Dentroctonus brevicomis. Chem. Soc., Perkin Trans. 1 (1991) 1419-1421
2. Branneby C., Carlqvist P., Magnusson A., Hult K., Brinck T., and Berglund P. Carbon-carbon bonds by hydrolytic enzymes. J. Am. Chem. Soc. 125 (2002) 874-875
3. Bornscheuer U.T., and Kazlauskas R.J. Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways. Angew. Chem. Int. Ed. 43 (2004) 6032-6040
4. Boruwa J., Gogoi N., Saikia P.P., and Barua C.C. Catalytic asymmetric Henry reaction. Tetrahedron: Asymmetry 17 (2006) 3315-3326
5. Bosica G., and Ballini R. Nitroaldol reaction in aqueous media: an important improvement of the Henry reaction. J. Org. Chem. 62 (1997) 425-427
6. 3-mediated conversion of secondary nitroalkanes to ketones: a very mild Nef-type process. Tetrahedron Lett. 49 (2008) 441-444
7. Cai Y., Sun X.F., Wang N., and Lin X.F. Alkaline protease from Bacillus subtilis catalyzed Michael addition of pyrimidine derivatives to alpha, beta-ethylenic compounds in organic media. Synthesis (2004) 671-674
8. Carlqvist P., Svedendahl M., Branneby C., Hult K., Brinck T., and Berglund P. Exploring the active-site of a rationally redesigned lipase for catalysis of Michael-type additions. ChemBioChem 6 (2005) 331-336
9. Copley S.D. Enzymes with extra talents: moonlighting functions and catalytic promiscuity. Curr. Opin. Chem. Biol. 7 (2003) 265-272
10. Gruber K.M., Purkarthofer T., Skranc W., and Griengl H. Hydroxynitrile lyase-catalyzed enzymatic nitroaldol (Henry) reaction. Adv. Synth. Catal. 349 (2007) 1445-1450
11. Heffner R.J., Jiang J., and Jouillie M.M. Total synthesis of (-)-nummularine F. J. Am. Chem. Soc. 114 (1992) 10181-10189
12. Hult K., and Berglund P. Enzyme promiscuity: mechanism and applications. Trends Biotechnol. 25 (2007) 231-238
13. Khersonsky O., Roodveldt C., and Tawfik D.S. Enzyme promiscuity: evolutionary and mechanistic aspects. Curr. Opin. Chem. Biol. 10 (2006) 498-508
14. 3N: an efficient promoter for the nitroaldol (Henry) reaction. J. Org. Chem. 64 (1999) 4298-4303
15. Kitazume T., Ikeya T., and Murata K. Synthesis of optically active trifluorinated compounds: asymmetric Michael addition with hydrolytic enzymes. J. Chem. Soc. Chem. Commun. (1986) 1331-1333
16. Kiyooka S., Tsutsui T., Maeda H., Kaneko Y., and Isobe K. A novel nitroaldol reaction catalyzed by rhodium complex in hte presence of a silyl ketene acetal. Tetrahedron Lett. 36 (1995) 6531-6534
17. Li C., Feng X.W., Wang N., Zhou Y.J., and Yu X.Q. Biocatalytic promiscuity: the first lipase-catalysed asymmetric aldol reaction. Green Chem. 10 (2008) 616-618
18. Li H., Wang B., and Deng L. Enantioselective nitroaldol reaction of α-ketoesters catalyzed by cinchona alkaloids. J. Am. Chem. Soc. 128 (2006) 732-733
19. Liu B.K., Qian X.Q., Wu Q., and Lin X.F. Two lipase-catalyzed sequential synthesis of drug derivatives in organic media. Enzyme Microb. Technol. 43 (2008) 375-380
20. Lopez E.M., Merino P., Tejero T., and Herrera R.P. Catalytic enantioselective aza-Henry reactions. Eur. J. Org. Chem. 15 (2009) 2401-2420
21. Lou F.W., Liu B.K., Wu Q., Lv D.S., and Lin X.F. Candida antarctica lipase B (CAL-B)-catalyzed carbon-sulfur bond addition and controllable selectivity in organic media. Adv. Synth. Catal. 350 (2008) 1959-1962
22. Luzzio F.A. The Henry reaction: recent examples. Tetrahedron 57 (2001) 915-945
23. Ma J.A. Recent developments in the catalytic asymmetric synthesis of α- and β-amino acids. Angew. Chem. Int. Ed. 42 (2003) 4290-4299
24. Marcelli T., van der Haas R.N.S., van Maarseveen J.H., and Hiemstra H. Cinchona derivatives as bifunctional organocatalysts for the direct asymmetric nitroaldol (Henry) reaction. Synlett (2005) 2817-2819
25. Mikite G., Jakucs K., Darvas F., and Lopata A. Synthesis and antifungal activity of new nitro-alcohol derivatives. Pest Sci. 13 (1982) 557-562
26. O'Brien P.J., and Herschlag D. Catalytic promiscuity and the evolution of new enzymatic activities. Chem. Biol. 6 (1999) R91-R105
27. Palomo C., Oiarbide M., and Laso A. Recent advances in the catalytic asymmetric nitroaldol (Henry) reaction. Eur. J. Org. Chem. 16 (2007) 2561-2574
28. Purkarthofer T., Gruber K.M., Khadjawi M.G., Waich K., Skranc W., Mink D., and Griengl H. A biocatalytic Henry reaction - the hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions. Angew. Chem. Int. Ed. 45 (2006) 3454-3456
29. Rodrigo O.M.A., Matos L.M.C., Goncalves K.M., Costa I.C.R., Babics L., Leite S.G.F., Oestreicher E.G., and Antunes O.A.C. Michael additions of primary and secondary amines to acrylonitrile catalyzed by lipases. Tetrahedron Lett. 50 (2009) 2017-2018
30. Rosini G., and Ballini R. Functionalized nitroalkanes as useful reagents for alkyl anion synthons. Synthesis (1988) 833-847
31. Rosini G., and Trost B.M. Comprehensive Organic Synthesis (1991), Pergamon, New York pp. 321-340
32. Sakanaka O., Ohmorti T., Kazaki S., Suami T., Ishii T., Ohba S., and Saito Y. Synthetic approach toward antibiotic ezomycins. I. Synthesis of 5-amino-5-deoxyoctofuranose-(1,4) derivatives by Henry reaction and their stereochemistry. Bull. Chem. Soc. Jpn. 59 (1986) 1753-1759
33. Seebeck F.P., and Hilvert D. Conversion of a PLP-dependent racemase into an aldolase by a single active site mutation. J. Am. Chem. Soc. 125 (2003) 10158-10159
34. Suami T., Sasai H., and Matsuno K. Synthesis of methyl hexaacetyl-tunicaminyl uracil. Chem. Lett. (1983) 819-822
35. Svedendahl M., Hult K., and Berglund P. Fast carbon-carbon bond formation by a promiscuous lipase. J. Am. Chem. Soc. 127 (2005) 17988-17989
36. Terao Y., Miyamoto K., and Ohta H. The aldol type reaction catalyzed by arylmalonate decarboxylase - a decarboxylase can catalyze an entirely different reaction, aldol reaction. Chem. Lett. 36 (2007) 420-421
37. Torre O., Alfonso I., and Gotor V. Lipase catalyzed Michael addition of secondary amines to acrylonitrile. Chem. Commun. (2004) 1724-1725
38. Wu W.B., Wang N., Xu J.M., Wu Q., and Lin X.F. Penicillin G acylase catalyzed Markovnikov addition of allopurinol to vinyl ester. Chem. Commun. 18 (2005) 2348-2350
39. Wu W.B., Xu J.M., Wu Q., Lv D.S., and Lin X.F. Promiscuous acylases-catalyzed Markovnikov addition of N-heterocycles to vinyl esters in organic media. Adv. Synth. Catal. 348 (2006) 487-492
40. Xu J.M., Zhang F., Liu B.K., Wu Q., and Lin X.F. Promiscuous zinc-dependent acylase-mediated carbon-carbon bond formation in organic media. Chem. Commun. 20 (2007) 2078-2080