Title : Chlorogenate hydrolase-catalyzed synthesis of hydroxycinnamic acid ester derivatives by transesterification, substitution of bromine, and condensation reactions - Kishimoto_2005_Appl.Microbiol.Biotechnol_68_198 |
Author(s) : Kishimoto N , Kakino Y , Iwai K , Fujita T |
Ref : Applied Microbiology & Biotechnology , 68 :198 , 2005 |
Abstract :
A chlorogenate hydrolase (EC 3.1.1.42) synthesized 2-phenylethyl caffeate (2-CAPE) from 5-chlorogenic acid (5-CQA) and 2-phenylethyl alcohol (2-PA) (by transesterification), from 5-CQA and 2-phenylethyl bromide (2-PBr) (by substitution of bromine), and from caffeic acid (CA) and 2-PA or 2-PBr (by condensation) as well as hydrolysis of 5-CQA. Some reaction conditions including pH, temperature, substrate and solvent concentrates, and reaction time were optimized for the production of 2-CAPE. A maximal molar yield of 50% was achieved by transesterification, 4.7% by substitution of bromine, and 13% by condensation. Among the parameters studied for optimization, the pH of the buffer solution and concentration of 2-PA or 2-PBr affected the production of 2-CAPE. The optimum pH for the hydrolysis reaction was within the neutral range (pH 6.5), whereas the residual three reactions were only catalyzed within the acidic range (pH 3.0-4.0). The optimum concentrations of 2-PA and 2-PBr for three reactions were 5-70 vol% and no 2-CAPE was produced in the 2-PA or 2-PBr solutions containing powdered enzyme. The enzyme may bind to the caffeoyl moiety of 5-CQA or CA to form an enzyme-substrate complex. It then catalyzes four different reactions corresponding to the reaction conditions. |
PubMedSearch : Kishimoto_2005_Appl.Microbiol.Biotechnol_68_198 |
PubMedID: 15717173 |
Substrate | (2-Bromoethyl)benzene |
Kishimoto N, Kakino Y, Iwai K, Fujita T (2005)
Chlorogenate hydrolase-catalyzed synthesis of hydroxycinnamic acid ester derivatives by transesterification, substitution of bromine, and condensation reactions
Applied Microbiology & Biotechnology
68 :198
Kishimoto N, Kakino Y, Iwai K, Fujita T (2005)
Applied Microbiology & Biotechnology
68 :198