Chemoenzymatic semisynthesis of caffeic acid β-phenethyl ester, an antioxidative component in propolis, from raw coffee bean extract

• Published in: Bioscience, Biotechnology, and Biochemistry
• Main Authors: Hashimoto, Riichi, Iai, Hiyori, Fujita, Rie, Hanaya, Kengo, Higashibayashi, Shuhei, Inoue, Hiroyoshi, Sugai, Takeshi
• Other Authors: Japan Society for the Promotion of Science
• Format: Article in Journal/Newspaper
• Language: English
• Published: Oxford University Press (OUP) 2020
• Subjects: Organic Chemistry; Molecular Biology; Applied Microbiology and Biotechnology; General Medicine; Biochemistry; Analytical Chemistry; Biotechnology; Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1093/bbb/zbaa077; http://academic.oup.com/bbb/article-pdf/85/3/476/36660781/zbaa077.pdf

ABSTRACT 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.