Biocatalytic Knoevenagel reaction using alkaline protease from Bacillus licheniformis

References

• Barluenga J, Riesgo L, Vicente R, Luis AL, Tomás M. 2007. Rearrangement of propargylic esters: met al-based stereospecific synthesis of (E)- and (Z)-knoevenagel derivatives. J Am Chem Soc 129:7772–7773.
   PubMedGoogle Scholar
• Bartoli G, Bosco M, Carlone A, Dalpozzo R, Galzerano P, Melchiorre P, Sambri L. 2008. Magnesium perchlorate as efficient Lewis acid for the Knoevenagel condensation between β-diketones and aldehydes. Tetrahedron Lett 49:2555–2557.
   Web of Science ®Google Scholar
• Bornscheuer UT, Kazlauskas RJ. 2004. Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways. Angew Chem Int Ed 43:6032–6040.
   PubMed Web of Science ®Google Scholar
• Busto E, Gotor-Fernández V, Gotor V. 2010. Hydrolases: catalytically promiscuous enzymes for non-conventional reactions in organic synthesis. Chem Soc Rev 39:4504–4523.
   PubMed Web of Science ®Google Scholar
• Cabello JA, Campelo JM, Garcia A, Luna D, Marinas JM. 1984. Knoevenagel condensation in the heterogeneous phase using aluminum phosphate-aluminum oxide as a new catalyst. J Org Chem 49:5195–5197.
   Web of Science ®Google Scholar
• Cai JF, Guan Z, He YH. 2011. The lipase-catalyzed asymmetric C–C Michael addition. J Mol Catal B Enzym 68:240–244.
   Web of Science ®Google Scholar
• Chen X, Liu BK, Kang H, Lin XF. 2011. A tandem Aldol condensation/dehydration co-catalyzed by acylase and N-heterocyclic compounds in organic media. J Mol Catal B Enzym 68: 71–76.
   Google Scholar
• Deng L, Xu MX. 2002. Synthesis of 4-thienyl substituted dihydropyridines derivatives. Huaxi Yaoxue Zazhi 1:37–38.
   Google Scholar
• Dhake KP, Tambade PJ, Singhal RS, Bhanage BM. 2010. Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates. Tetrahedron Lett 51:4455–4458.
   Google Scholar
• Evitt AS, Bornscheuer UT. 2011. Lipase CAL-B does not catalyze a promiscuous decarboxylative aldol addition or Knoevenagel reaction. Green Chem 13:1141–1142.
   Web of Science ®Google Scholar
• Fan H, Kitagawa M, Rakub T, Tokiwa Y. 2003. Role of water activity on the synthesis of vinyl thymidine catalyzed by protease from Bacillus Subtilis. Macromol Biosci 3:420–424.
   Google Scholar
• Feng XW, Li C, Wang N, Li K, Zhang WW, Wang Z, Yu XQ. 2009. Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction. Green Chem 11:1933–1936.
   Web of Science ®Google Scholar
• Fessner WD, Anthonsen T 2009. Modern biocatalysis: stereoselective and environmentally friendly reactions. New York: Wiley-VCH.
   Google Scholar
• Fuhshuku K, Asano Y. 2011. Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous–organic biphasic system. J Biotechnol 153:153–159.
   PubMed Web of Science ®Google Scholar
• Ghosh S, Das J, Chattopadhyay S. 2011. A novel light induced Knoevenagel condensation of Meldrum's acid with aromatic aldehydes in aqueous ethanol. Tetrahedron Lett 52:2869–2872.
   Google Scholar
• He T, Li K, Wu MY, Feng XW, Wang N, Wang HY, Li C, Yu XQ. 2010. Utilization of biocatalytic promiscuity for direct Mannich reaction. J Mol Catal B Enzym 67:189–194.
   Web of Science ®Google Scholar
• Hu Y, Guan Z, He YH, Louwagie N, Yao MJ. 2010a. L-Arginine as a cost-effective and recyclable catalyst for the synthesis of α,β-unsaturated nitriles and ketones in an ionic liquid. J Chem Res 34:22–24.
   Google Scholar
• Hu Y, He YH, Guan Z. 2010b. A simple method for the preparation of functionalized trisubstituted alkenes and α,β,γ,δ-unsaturated carbonyl compounds by using natural amino acid l-tryptophan. Catal Commun 11:656–659.
   Google Scholar
• Humble MS, Berglund P. 2011. Biocatalytic promiscuity. Eur J Org Chem 2011:3391–3401.
   Web of Science ®Google Scholar
• Jones G. 1967. Organic reactions. New York: Wiley.
   Google Scholar
• Khurana JM, Vij K. 2011. Nickel nanoparticles catalyzed chemoselective Knoevenagel condensation of Meldrum's acid and tandem enol lactonizations via cascade cyclization sequence. Tetrahedron Lett 52:3666–3669.
   Google Scholar
• Kourist R, Bartsch S, Fransson L, Hult K, Bornscheuer UT. 2008. Understanding promiscuous amidase activity of an esterase from Bacillus subtilis. ChemBioChem 9:67–69.
   PubMedGoogle Scholar
• Klibanov AM. 1989. Enzymatic catalysis in anhydrous organic solvents. Trends Biochem Sci 14:141–144.
   PubMed Web of Science ®Google Scholar
• Lai YF, Zheng H, Chai SJ, Zhang PF, Chen XZ. 2010. Lipase-catalysed tandem Knoevenagel condensation and esterification with alcohol cosolvents. Green Chem 12:1917–1918.
   Google Scholar
• Lehnert W. 1970. Verbesserte variante der knoevenagel-kondensation mit TiCl4/THF/pyridin(I). Alkyliden- und Arylidenmalonester bei 0–25°C. Tetrahedron Lett 11:4723–4724.
   Google Scholar
• Li C, Hassler M, Bugg TDH. 2008. Catalytic promiscuity in the α/β-hydrolase superfamily: hydroxamic acid formation, C-C bond formation, ester and thioester hydrolysis in the C-C hydrolase family. ChemBioChem 9:71–76.
   PubMedGoogle Scholar
• Li C, Zhou YJ, Wang N, Feng XW, Li K, Yu XQ. 2010a. Promiscuous protease-catalyzed aldol reactions: a facile biocatalytic protocol for carbon–carbon bond formation in aqueous media. J Biotechnol 150:539–545.
   PubMedGoogle Scholar
• Li HH, He YH, Yuan Y, Guan Z. 2011. Nuclease p1: a new biocatalyst for direct asymmetric aldol reaction under solvent-free conditions. Green Chem 13:185–189.
   Google Scholar
• Li JL, Kang TR, Zhou SL, Li R, Wu L, Chen YC. 2010b. Organocatalytic asymmetric inverse-electron-demand Diels–Alder reaction of electron-deficient dienes and crotonaldehyde. Angew Chem Int Ed 49:6418–6420.
   PubMedGoogle Scholar
• López-Iglesias M, Busto E, Gotor V, Gotor-Fernández V. 2011. Use of protease from Bacillus licheniformis as promiscuous catalyst for organic synthesis: applications in C-C and C-N bond formation reactions. Adv Synth Catal 353:2345–2353.
   Web of Science ®Google Scholar
• Lorsbach BA, Kurth MJ. 1999. Carbon−carbon bond forming solid-phase reactions. Chem Rev 99:1549–1582.
   PubMedGoogle Scholar
• Lou FW, Liu BK, Wang JL, Pan Q, Lin XF. 2009. Controllable enzymatic Markovnikov addition and acylation of thiols to vinyl esters. J Mol Catal B Enzym 60:64–68.
   Web of Science ®Google Scholar
• Lyall R, Zilberstein A, Gazit A, Gilon C, Levitzki A, Schlessinger J. 1989. Tyrphostins inhibit epidermal growth factor (EGF)-receptor tyrosine kinase activity in living cells and EGF-stimulated cell proliferation. J Biol Chem 2649:14503–14509.
   Google Scholar
• Mahendra PP, Akhilesh KS, Raghavan BS. 2010. Importance of the nature of α-substituents in pyrrolidine organocatalysts in asymmetric michael additions. J Org Chem 75:7310–7321.
   PubMedGoogle Scholar
• Prajapati D, Sandhu JS. 1993. ChemInform abstract: cadmium iodide as a new catalyst for knoevenagel condensations. J Chem Soc Perkin Trans 1:739–740.
   Google Scholar
• Ranu BC, Jana R. 2006. Ionic liquid as catalyst and reaction medium -a simple, efficient and green procedure for Knoevenagel condensation of aliphatic and aromatic carbonyl compounds using a task-specific basic ionic liquid. Eur J Org Chem 16:3767–3770.
   Web of Science ®Google Scholar
• Rao PS, Venkataratnam RV. 1991. Zinc chloride as a new catalyst for knoevenagel condensation. Tetrahedron Lett 32:5821–5822.
   Web of Science ®Google Scholar
• Reddy TI, Varma RS. 1997. Rare-earth (RE) exchanged NaY zeolite promoted knoevenagel condensation. Tetrahedron Lett 38:1721–1724.
   Web of Science ®Google Scholar
• Shanmuganathan S, Greiner L, Domínguez de María P. 2010. Silica-immobilized piperazine: a sustainable organocatalyst for aldol and Knoevenagel reactions. Tetrahedron Lett 51:6670–6672.
   Web of Science ®Google Scholar
• Shiraishi T, Owada MK, Tatsuki M, Yamashita Y, Kaun-aga T. 1989. Specific inhibitors of tyrosine-specific protein kinases: properties of 4-hydroxycinnamamide derivatives in Vitro. Cancer Res 49:2374–2378.
   PubMed Web of Science ®Google Scholar
• Sonawane YA, Phadtare SB, Borse BN, Jagtap Amit R, Shankarling GS. 2010. Synthesis of diphenylamine-based novel fluorescent styryl colorants by Knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent. Org Lett 12:1456–1459.
   PubMed Web of Science ®Google Scholar
• Texier-Boullet F, Foucaud A. 1982. Knoevenagel condensation catalysed by aluminium oxide. Tetrahedron Lett 23:4927–4928.
   Web of Science ®Google Scholar
• Tietze LF, Beifuss U. 1991. In comprehensive organic synthesis. Pergamon: Oxford.
   Google Scholar
• Wang CH, Guan Z, He YH. 2011. Biocatalytic domino reaction: synthesis of 2H-1-benzopyran-2-one derivatives using alkaline protease from Bacillus licheniformis. Green Chem 13:2048–2054.
   Web of Science ®Google Scholar
• Wang JL, Li X, Xie HY, Liu BK, Lin XF. 2010a. Hydrolase-catalyzed fast Henry reaction of nitroalkanes and aldehydes in organic media. J Biotechnol 145:240–243.
   PubMed Web of Science ®Google Scholar
• Wang L, Li C, Wang N, Li K, Chen X, Yu XQ. 2010b. Enzyme-mediated domino synthesis of 2-alkylbenzimidazoles in solvent-free system: a green route to heterocyclic compound. J Mol Catal B Enzym 67:16–20.
   Google Scholar
• Wu Q, Liu BK, Lin XF. 2010. Enzymatic promiscuity for organic synthesis and cascade process. Curr Org Chem 14:1966–1988.
   Google Scholar
• Xin X, Guo X, Duan HF, Lin YJ, Sun H. 2007. Efficient Knoevenagel condensation catalyzed by cyclic guanidinium lactate ionic liquid as medium. Catal Commun 8:115–117.
   Web of Science ®Google Scholar
• Xu JM, Zhang F, Liu BK, Wu Q, Lin XF. 2007. Promiscuous zinc-dependent acylase-mediated carbon–carbon bond formation in organic media. Chem Commun 2007:2078–2080.
   Google Scholar
• Xu KL, Guan Z, He YH. 2011. Acidic proteinase from Aspergillus usamii catalyzed Michael addition of ketones to nitroolefins. J Mol Catal B Enzym 71:108–112.
   Google Scholar
• Yadav JS, Bhunia DC, Singh VK, Srihari P. 2009. Solvent-free NbCl5 catalyzed condensation of 1,3-dicarbonyl compounds and aldehydes: a facile synthesis of trisubstituted alkenes. Tetrahedron Lett 50:2470–2473.
   Google Scholar