Hydrolase-catalyzed Michael addition of imidazoles to acrylic monomers in organic medium.
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.
Cai
Ying
Y
Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
Wu
Qi
Q
Xiao
Yong-Mei
YM
Lv
De-Shui
DS
Lin
Xian-Fu
XF
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
D000179:Acrylates; D001426:Bacterial Proteins; D007093:Imidazoles; D009930:Organic Chemicals; D012997:Solvents; D006867:Hydrolases; D010450:Endopeptidases; C087822:alkaline protease