title: First Novozym 435 lipase-catalyzed Morita-Baylis-Hillman reaction in the presence of amides.
abstract: The first Novozym 435 lipase-catalyzed Morita-Baylis-Hillman (MBH) reaction with amides as co-catalyst was realized. Results showed that neither Novozym 435 nor amide can independently catalyze the reaction. This co-catalytic system that used a catalytic amount of Novozym 435 with a corresponding amount of amide was established and optimized. The MBH reaction strongly depended on the structure of aldehyde substrate, amide co-catalyst, and reaction additives. The optimized reaction yield (43.4%) was achieved in the Novozym 435-catalyzed MBH reaction of 2, 4-dinitrobenzaldehyde and cyclohexenone with isonicotinamide as co-catalyst and β-cyclodextrin as additive only in 2 days. Although enantioselectivity of Novozym 435 was not found, the results were still significant because an MBH reaction using lipase as biocatalyst was realized for the first time.
authors.affiliation: College of Life Sciences, Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130012, People's Republic of China; College of Chemistry, Jilin University, Changchun 130012, People's Republic of China.
authors.forename: Xuemei
authors.initials: X
authors.lastname: Tian
authors.affiliation: College of Chemistry, Jilin University, Changchun 130012, People's Republic of China.
authors.forename: Suoqin
authors.initials: S
authors.lastname: Zhang
authors.affiliation: College of Life Sciences, Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130012, People's Republic of China. Electronic address: lyzheng@jlu.edu.cn.
authors.forename: Liangyu
authors.initials: L
authors.lastname: Zheng
mesh_terms: D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D000577:Amides / Q000737:chemistry / Q000378:metabolism; D055162:Biocatalysis; D003505:Cyclodextrins / Q000737:chemistry / Q000378:metabolism; D004800:Enzymes, Immobilized / Q000378:metabolism; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D008954:Models, Biological; D009536:Niacinamide / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000447:Aldehydes; D000577:Amides; D003505:Cyclodextrins; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D009536:Niacinamide; C093667:Novozyme 435; D008049:Lipase
keywords: Amides; Co-catalyst; MBH reaction; Novozym 435 lipase