Enzymatic synthesis of caffeic acid phenethyl ester analogues in ionic liquid

Kurata, Atsushi; Kitamura, Yuki; Irie, Shiori; Takemoto, Shintaro; Akai, Yoshiaki; Hirota, Yoshitaka; Fujita, Takumi; Iwai, Kento; Furusawa, Mina; Kishimoto, Noriaki

doi:10.1016/j.jbiotec.2010.05.007

Cited by 52 publications

(23 citation statements)

References 26 publications

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“…Lipases used in this work are widely employed as biocatalysts, but exhibit different substrate specificity. Kurata et al [19] also reported that Novozym 435 displayed the highest activity in the transesterification of methyl caffeate with 3-cyclohexyl-1-propanol using [Bmim][Tf 2 N]. Therefore, Novozym 435 was chosen to catalyze esterification of CA in both ILs and isooctane for the following study.…”

Section: Selection Of Enzymementioning

confidence: 99%

Effect of ionic liquids on enzymatic synthesis of caffeic acid phenethyl ester

Anh

Lee

et al. 2011

Bioprocess Biosyst Eng

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Although caffeic acid phenethyl ester (CAPE), an active flavonoid, plays an important role in the antioxidant activity of honeybee propolis, the isolation of CAPE from honeybee propolis is time-consuming due to wide variety of impurities present. Therefore, biochemical method to synthesize CAPE was investigated in this study. Since ionic liquids (ILs) possess some unique characteristics as appreciated alternatives to conventional solvents for certain biotransformation, the effect of ILs as reaction media for enzymatic synthesis of CAPE was assessed. Several factors including substrate molar ratio, and reaction temperature affecting the conversion yield of lipase-catalyzed CAPE synthesis were also investigated. Reaction yields were significantly higher in hydrophobic ILs than in hydrophilic ILs (almost zero). Among nine hydrophobic ILs tested, the highest conversion of synthetic reaction was obtained in 1-ethyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([Emim][Tf(2)N]). A reaction temperature of 70 °C was found to give high conversion. In addition, optimal substrate molar ratio between phenethyl alcohol and caffeic acid (CA) was decreased significantly from 92:1 to 30:1 when ILs were used instead of isooctane.

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Section: Selection Of Enzymementioning

confidence: 99%

Effect of ionic liquids on enzymatic synthesis of caffeic acid phenethyl ester

Anh

Lee

et al. 2011

Bioprocess Biosyst Eng

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show abstract

“…Lipases, noted for their tolerance of organic solvents, are obvious candidates for the enzymatic synthesis in ILs (Sureshkumar & Lee, 2009). Kurata et al (Kurata et al, 2010) described a transesterification reaction of methyl caffeate with various alcohols to produce caffeic acid phenethyl ester (CAPE) analogues with a lipase using an IL as the reaction medium. Effect of ILs on immobilized lipase B from Candida antarctica -CALB (Novozyme 435) showed that the anion nature is a crucial factor in determining enzyme activity.…”

Section: An Overview Of Biocatalysis In Ils and In Scfs/ils Systemsmentioning

confidence: 99%

Application of Ionic Liquids in Biocatalysis

Habulin¹,

Primožič²,

Knez³

2011

Ionic Liquids: Applications and Perspectives

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“…We examined the production of CAPE analogues using transesterification with [bmim][NTf 2 ] (Kurata et al, 2010). CAPE analogues were produced using 50 mM methyl caffeate (50 µmol) and 300 mM alcohols (300 µmol).…”

Section: Substrate Specificity For Novozyme 435mentioning

confidence: 99%

“…], which was used as a reaction medium. For production of 2-cyclohexylethyl caffeate, 3-cyclohexylpropyl caffeate, 4-phenylbutyl caffeate, and 5-phenylpentyl caffeate, alchols used were shown as follows: 2-cyclohexylethanol, 3-cyclohexyl-1-propanol, 4-phenyl-1-butanol, 5-phenyl-1-pentanol, respectively (Kurata et al, 2010).…”

Section: Substrate Specificity For Novozyme 435mentioning

confidence: 99%

“…In the synthesis of CAPE analogues, the conversion yield of 3-cyclohexylpropyl caffeate toward 5-caffeoylquinic acid (85.3%) was superior to that of CAPE toward 5-caffeoylquinic acid (50%) (Kishimoto et al, 2005a). CAPE analogues were obtained by single transesterification systems catalyzed by Novozyme 435 using [bmim][NTf 2 ] or isooctane as the solvent with conversion yields of 93.8% and 91.65%, respectively (Chen et al, 2010;Kurata et al, 2010). The conversion yield of 3-cyclohexylpropyl caffeate produced by the consecutive conversion system was comparable to those of CAPE produced by single transesterification systems.…”

Section: Consecutive Enzymatic Reactions For Synthesis Of 3-cyclohexymentioning

confidence: 99%

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