To overcome the poor properties of solubility and stability of cinnamic acid, cinnamate derivatives with sugar alcohols were produced using the immobilized Candida antarctica lipase with vinyl cinnamate and D-sorbitol as substrate at 45 degrees C. Immobilized C. antarctica lipase was found to synthesize 6-O-cinnamoyl-sorbitol and confirmed by HPLC and (1)H-NMR and had a preference for vinyl cinnamate over other esters such as allyl-, ethyl-, and isobutyl cinnamate as co-substrate with D-sorbitol. Contrary to D-sorbitol, vinyl cinnamate, and cinnamic acid, the final product 6-O-cinnamoyl-sorbitol was found to have radical scavenging activity. This would be the first report on the biosynthesis of 6-O-cinnamoyl-sorbitol with immobilized enzyme from C. antarctica.
Kim JH, Bhatia SK, Yoo D, Seo HM, Yi DH, Kim HJ, Lee JH, Choi KY, Kim KJ, Lee YK, Yang YH (2015) Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters Appl Biochem Biotechnol176: 244-52
Kim JH, Bhatia SK, Yoo D, Seo HM, Yi DH, Kim HJ, Lee JH, Choi KY, Kim KJ, Lee YK, Yang YH (2015) Appl Biochem Biotechnol176: 244-52