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

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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-O-cinnamoyl-sorbitol with immobilized enzyme from C. antarctica.

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Acknowledgments

The authors follow the Instructions for Authors to make sure their manuscript complies to the ethical rules applicable for this journal. The study was partially supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2013R1A1A2A10004690), by KOPRI (PE14030), and by the R& D Program of MOTIE/KEIT (10048350) and “Cooperative Research Program for Agriculture Science & Technology Development (Project title: Isolation and identification of rhizobacteria for indoor VOCs removal, Project No. 010205022014)” Rural Development Administration, Republic of Korea. In addition, this research was supported by the 2014 KU Brain Pool of Konkuk University.

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    Authors and Affiliations

    1. Department of Biological Engineering, College of Engineering, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul, 143-701, South Korea

      Jung-Ho Kim, Shashi Kant Bhatia, Hyung Min Seo, Da-Hye Yi, Hyun Joong Kim, Ju Hee Lee & Yung-Hun Yang

    2. School of Chemical and Biological Engineering, Seoul National University, Gwanak-Gu, Seoul, 151-742, South Korea

      Dongwon Yoo

    3. Department of Environmental Engineering, Ajou University, 206, World cup-ro, Yeongtong-gu, Suwon, Gyeonggi-do, 443-749, South Korea

      Kwon-Young Choi

    4. National Institute of Horticultural and Herbal Science, Suwon, 441-440, South Korea

      Kwang Jin Kim

    5. Division of Life Sciences, Korea Polar Research Institute, 12 Gaetbeol-ro, Yeonsu-gu, Incheon, 406-840, South Korea

      Yoo Kyung Lee

    6. Institute for Ubiquitous Information Technology and Applications (CBRU), Konkuk University, Seoul, 143-701, South Korea

      Yung-Hun Yang

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    1. Jung-Ho Kim
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    Correspondence to Yung-Hun Yang.

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    Jung-Ho Kim and Shashi Kant Bhatia contributed equally to this work.

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    Fig. S1

    HPLC chromatogram of each compound with their retention time, i.e., RT = 3.4 for 6-O-cinnamoyl-sorbitol, 4.3 for cinnamic acid, and 64.6 min for vinyl cinnamate (DOC 76 kb).

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    Kim, JH., Bhatia, S.K., Yoo, D. et al. Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters. Appl Biochem Biotechnol 176, 244–252 (2015). https://doi.org/10.1007/s12010-015-1570-x

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    • DOI: https://doi.org/10.1007/s12010-015-1570-x

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