title: Enzyme-Catalyzed Asymmetric Domino Thia-Michael/Aldol Condensation Using Pepsin.
abstract: The novel catalytic promiscuity of pepsin from porcine gastric mucosa for the asymmetric catalysis of the domino thia-Michael/aldol condensation reaction in MeCN and buffer was discovered for the first time. Broad substrate specificity was tested, and a series of corresponding products were obtained with enantioselectivities of up to 84% ee. This specific catalysis was demonstrated by using recombinant pepsin and control experiments with denatured and inhibited pepsin. The reaction was also shown to occur in the active site by site-directed mutagenesis (the Asp32Ala mutant of pepsin), and a possible mechanism was proposed.
authors.affiliation: Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University , Chongqing 400715, P. R. China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Xiang
authors.affiliation: Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University , Chongqing 400715, P. R. China.
authors.forename: Jian
authors.initials: J
authors.lastname: Song
authors.affiliation: Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University , Chongqing 400715, P. R. China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University , Chongqing 400715, P. R. China.
authors.forename: Da-Cheng
authors.initials: DC
authors.lastname: Yang
authors.affiliation: Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University , Chongqing 400715, P. R. China.
authors.forename: Zhi
authors.initials: Z
authors.lastname: Guan
authors.affiliation: Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University , Chongqing 400715, P. R. China.
authors.forename: Yan-Hong
authors.initials: YH
authors.lastname: He
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D020134:Catalytic Domain; D002851:Chromatography, High Pressure Liquid; D004798:Enzymes / Q000737:chemistry*; D005753:Gastric Mucosa / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D015394:Molecular Structure; D016297:Mutagenesis, Site-Directed; D009154:Mutation; D010434:Pepsin A / Q000737:chemistry*; D011994:Recombinant Proteins / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D013379:Substrate Specificity; D013552:Swine
chemical_list: D000447:Aldehydes; D004798:Enzymes; D011994:Recombinant Proteins; D012997:Solvents; C116609:3-hydroxybutanal; D010434:Pepsin A