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Theoretical design and preparation research of molecularly imprinted polymers for steviol glycosides

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Abstract

In this paper, a novel molecularly imprinted polymer (MIP) for specific adsorption of steviol glycosides was designed, and the imprinting mechanism of self-assembly system between template and monomers was clearly explored. Firstly, steviol (STE) was chosen as dummy template, and the density functional theory (DFT) at B3LYP/6–31 + G (d, p) level was used to select monomers, imprinting molar ratios, solvents, and cross-linking agents. The selectivity to five steviol glycosides was also calculated. Importantly, reduced density gradient (RDG) theory combined with atom in molecules (AIM) and infrared spectrum (IR) was applied to investigate the bonding situation and the nature of noncovalent interaction in self-assembly system. The theoretical designed results showed that the template which interacts with acrylic acid (AA) has the minimum binding energy, and the complex with the molar ratio of 1 : 4 has the most stable structure. Toluene (TL) and ethylene glycol dimethacrylate (EGDMA) were chosen as the optimal solvent and cross-linking agent, respectively. Five hydrogen bonds formed in the self-assembly system are the key forces at the adsorption sites of MIPs through the RDG and AIM analyses. The MIPs were synthesized by theoretical predictions, and the results showed that the maximum adsorption capacity towards dulcoside A is 26.17 mg/g. This work provided a theoretical direction and experimental validation for deeper researches of the MIPs for steviol glycosides. In addition, the method of RDG theory coupled with AIM and IR also could be used to analyze other imprinting formation mechanisms systematically.

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Data availability

The datasets used and analyzed during the current study are available from the corresponding author on reasonable request.

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Funding

High-level talents project of Dalian City (2016RQ064); Research Foundation of Education Bureau of Liaoning Province (2016J008); National Natural Science Foundation of China (U1603285).

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Authors and Affiliations

  1. School of Food Science and Technology, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Yajie Zhu, Yan Ding, Yan Li, Linwu Zhuang, Yinpeng Wang & Jingbo Zhu

  2. Institute of Chemistry and Applications of Plant Resources, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Yan Ding & Jingbo Zhu

  3. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, No 2 Linggong Road, Liaoning, 116024, China

    Dongxu Tian

  4. Jiangsu Kanion Pharmaceutical Co. Ltd., Lianyungang, Jiangsu, 222000, People’s Republic of China

    Wei Xiao

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  1. Yajie Zhu
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  2. Yan Ding
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  4. Yan Li
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Contributions

Yajie Zhu, Yan Ding, and Yan Li designed and conceived the study; Yajie Zhu and Dongxu Tian analyzed the data and drafted the manuscript; Dongxu Tian, Yan Li, Lin-Wu Zhuang, Yinpeng Wang, and Wei Xiao provided advice and technical assistance; Jingbo Zhu provided advice and funding. Yan Ding revised the manuscript. All authors have contributed to and approved the final manuscript.

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Correspondence to Yan Ding or Jingbo Zhu.

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Zhu, Y., Ding, Y., Tian, D. et al. Theoretical design and preparation research of molecularly imprinted polymers for steviol glycosides. J Mol Model 27, 238 (2021). https://doi.org/10.1007/s00894-021-04819-9

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