title: Hydrolase-catalyzed Michael addition of imidazoles to acrylic monomers in organic medium.
abstract: Hydrolase-catalyzed Michael addition of imidazole derivatives to acrylic monomers in organic medium was described. A serial of N-substituted imidazole derivatives were successfully synthesized in moderate yields by the catalysis of hydrolases in organic medium. Nine commercially available hydrolases from different sources were screened and all of them were found to be able to catalyze this type of addition reaction. The reaction yields depended on the solvent properties and the solvents with higher log P value supported this enzyme-catalyzed reaction to give higher conversion. Influence of the structure of the Michael acceptor and donor on the enzymatic Michael addition was also investigated. The acceptor with shorter alcohol chain afforded a higher yield. A more rapid conversion was observed when the donor had an electron-withdrawing group. This hydrolase-catalyzed Michael addition reaction has widened the applicability of biocatalysts in organic and bioorganic synthesis.
authors.affiliation: Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Cai
authors.forename: Qi
authors.initials: Q
authors.lastname: Wu
authors.forename: Yong-Mei
authors.initials: YM
authors.lastname: Xiao
authors.forename: De-Shui
authors.initials: DS
authors.lastname: Lv
authors.forename: Xian-Fu
authors.initials: XF
authors.lastname: Lin
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D001236:Aspergillus oryzae / Q000201:enzymology; D001412:Bacillus subtilis / Q000201:enzymology; D001426:Bacterial Proteins / Q000378:metabolism; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D010450:Endopeptidases / Q000378:metabolism; D006867:Hydrolases / Q000138:chemical synthesis / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009930:Organic Chemicals / Q000737:chemistry*; D012997:Solvents; D013696:Temperature; D013997:Time Factors
chemical_list: D000179:Acrylates; D001426:Bacterial Proteins; D007093:Imidazoles; D009930:Organic Chemicals; D012997:Solvents; D006867:Hydrolases; D010450:Endopeptidases; C087822:alkaline protease