title: Kinetically controlled enzymatic synthesis of dipeptide precursor of L-alanyl-L-glutamine.
abstract: An important nutritional dipeptide precursor, benzoyloxycarbonyl protected L-alanyl-L-glutamine (Z-Ala-Gln), was successfully prepared through a kinetically controlled enzymatic peptide synthesis method. A commercially available and low-cost protease (papain) was used as biocatalyst with Z-Ala-OMe and Gln as acyl donor and nucleophile, respectively. The dipeptide yield was 35.5% under the optimized reaction conditions: 35°C, pH 9.5, and the ratio of acyl donor/nucleophile is 1:10. Based on the reaction mechanism and experimental data, the kinetic model was established, which was in accordance with the Michaelis-Menten equation, and the apparent Michaelis constant K(m)(app) and the apparent maximum reaction rate r(max)(app) were calculated as 1.71 mol/L and 6.09 mmol/(L Min), respectively.
authors.affiliation: State Key Laboratory of Chemical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin, People's Republic of China.
authors.forename: Mengfan
authors.initials: M
authors.lastname: Wang
authors.forename: Wei
authors.initials: W
authors.lastname: Qi
authors.forename: Qingxin
authors.initials: Q
authors.lastname: Yu
authors.forename: Rongxin
authors.initials: R
authors.lastname: Su
authors.forename: Zhimin
authors.initials: Z
authors.lastname: He
mesh_terms: D060326:Chemistry Techniques, Synthetic; D002851:Chromatography, High Pressure Liquid; D004151:Dipeptides / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D013058:Mass Spectrometry; D010206:Papain / Q000737:chemistry; D013696:Temperature
chemical_list: D004151:Dipeptides; D010206:Papain; C054122:alanylglutamine