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Enzymatic synthesis of caffeic acid phenethyl ester analogues in ionic liquid

2010; Elsevier BV; Volume: 148; Issue: 2-3 Linguagem: Inglês

10.1016/j.jbiotec.2010.05.007

1873-4863

Atsushi Kurata, Yuki Kitamura, Shiori Irie, Shintaro Takemoto, Yoshiaki Akai, Yoshitaka Hirota, Tokio Fujita, Kazuya Iwai, Mina Furusawa, Noriaki Kishimoto,

Coffee research and impacts

An efficient procedure for transesterification of methyl caffeate was developed to produce caffeic acid phenethyl ester analogues with Candida antarctica lipase B using an ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, as a solvent. The system provided 48.8 mM 2-cyclohexylethyl caffeate and 46.9 mM 3-cyclohexylpropyl caffeate with conversion yields of 97.6% and 93.8%, respectively. Reusability of the system was investigated, and the yield of 4-phenylbutyl caffeate was increased from 30.4 to 45.7 mM when the transesterification was carried out under reduced pressure to remove a by-product, methanol. Additionally, we showed that both 2-cyclohexylethyl caffeate and 3-cyclohexylpropyl caffeate exhibit strong antiproliferative activities, which are comparable to that of 5-fluorouracil by MTT assay.