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Chemoenzymatic synthesis of 1,3-dioleoyl-2-palmitoylglycerol

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Abstract

We report the synthesis of 1,3-dioleoyl-2-palmitoylglycerol (OPO) by a three-step method. Vinyl oleate was first synthesized by transvinylation between vinyl acetate and oleic acid. This was further reacted with glycerol at 35 °C for 8 h using 10 % (w/v) Novozym 435 to synthesize 1,3-diolein. The 1,3-diolein content in the crude reaction mixture was 90.8 % and was obtained at 82.3 % (w/w) yield with 98.6 % purity after purification. Finally, OPO was chemically synthesized by reacting purified 1,3-diolein with palmitic acid. 94.8 % OPO was produced in the crude reaction mixture and the regiopurity of OPO after purification was 98.7 % at 90.5 % yield based on positional distribution analysis. This is an innovative approach for the synthesis of 1,3-diolein in a solvent-free system as an alternative to previously presented studies that applied solvent system.

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Acknowledgments

We acknowledge the Chinese Scholarship Council for providing the sponsorship to this work.

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Authors and Affiliations

  1. State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, 1800 Lihu Road, Wuxi, 214122, Jiangsu, People’s Republic of China

    Xiaosan Wang, Wanzhen Zou, Xuemei Sun, Yu Zhang, Liying Wei, Qingzhe Jin & Xingguo Wang

  2. Department of Food Science and Human Nutrition, Iowa State University, 2312 Food Science Building, Ames, IA, 50011, USA

    Xiaosan Wang

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  1. Xiaosan Wang
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  2. Wanzhen Zou
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  3. Xuemei Sun
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  4. Yu Zhang
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  5. Liying Wei
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  6. Qingzhe Jin
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  7. Xingguo Wang
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Correspondence to Xingguo Wang.

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Wang, X., Zou, W., Sun, X. et al. Chemoenzymatic synthesis of 1,3-dioleoyl-2-palmitoylglycerol. Biotechnol Lett 37, 691–696 (2015). https://doi.org/10.1007/s10529-014-1714-z

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  • DOI: https://doi.org/10.1007/s10529-014-1714-z

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