Hashimoto Riichi, Iai Hiyori, Fujita Rie, Hanaya Kengo, Higashibayashi Shuhei, Inoue Hiroyoshi, Sugai Takeshi
Department of Pharmaceutical Sciences, Faculty of Pharmacy, Keio University, Shibakoen, Minato-ku, Tokyo, Japan.
Yokohama Science Frontier High School, 6 Ono-cho, Tsurumi-ku, Yokohama, Japan.
Biosci Biotechnol Biochem. 2021 Feb 24;85(3):476-480. doi: 10.1093/bbb/zbaa077.
Caffeic acid β-phenethyl ester (CAPE), an antioxidative bioactive catechol isolated from propolis, was semisynthesized from chlorogenic acid and related compounds in an extract of raw (unroasted) Robusta coffee (Coffea canephora) beans in 5 steps and a total yield of 31%. Oxidative degradation of the intermediates and target molecule was prevented by alkaline hydrolysis of the chlorogenic acids in the presence of sodium dithionite (Na2S2O4) and deprotection of the catecholic diacetate precursor by Candida antarctica lipase B-mediated transesterification as the final step.
咖啡酸β-苯乙酯（CAPE）是一种从蜂胶中分离出来的具有抗氧化作用的生物活性儿茶酚，它由绿原酸及相关化合物经五步反应从生（未烘焙）罗布斯塔咖啡豆（卡内弗拉咖啡）提取物中半合成得到，总产率为31%。在连二亚硫酸钠（Na2S2O4）存在下对绿原酸进行碱性水解，并在最后一步通过南极假丝酵母脂肪酶B介导的酯交换反应对儿茶酚二乙酸酯前体进行脱保护，从而防止中间体和目标分子的氧化降解。
