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Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters

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Title
Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters
Authors
Kim, Jung-Ho
Bhatia, Shashi Kant
Yoo, Dongwon
Seo, Hyung Min
Yi, Da-Hye
Kim, Hyun Joong
Lee, Ju Hee
Choi, Kwon-Young
Kim, Kwang Jin
Lee, Yoo Kyung
Yang, Yung-Hun
Subject
Biochemistry & Molecular Biology; Biotechnology & Applied Microbiology
Keywords
6-O-cinnamoyl-sorbitol; Candida antarctica; Enzymatic synthesis; Lipase; Sorbitol
Issue Date
2014
Citation
Kim, Jung-Ho., et al. 2014. Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters. Appl Biochem Biotechnol, 176: 244-252.
Abstract
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 °C. Immobilized C. antarctica lipase was found to synthesize 6-O-cinnamoyl-sorbitol and confirmed by HPLC and 1H-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-Ocinnamoyl- sorbitol with immobilized enzyme from C. antarctica.
DOI
10.1007/s12010-015-1570-x
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