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A Density Functional Theory (DFT) Study of the Acyl Migration Occurring during Lipase-Catalyzed Transesterifications

1
State Key Laboratory of Food Science and Technology, Nanchang University, Jiangxi 330047, China
2
School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, China
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(14), 3438; https://doi.org/10.3390/ijms20143438
Received: 2 June 2019 / Revised: 7 July 2019 / Accepted: 10 July 2019 / Published: 12 July 2019
(This article belongs to the Section Macromolecules)
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Abstract

Acyl migration (AM) is the main side reaction in the large-scale, regio-specific lipase catalyzed production of structural triglycerides (STs). A detailed understanding of the mechanism of AM was obtained during the process of lipase-catalyzed schemes (LCSs), which play a vital role in improving the quality and total yield of STs. However, currently, the mechanism of AM remains controversial. Herein, the two mechanisms (non-catalyzed (NCM) and lipase-catalyzed (LCM)) of AM have been analyzed in detail by the density functional theory (DFT) at the molecular level. Based on the computational results, we concluded that the energy barrier of the rate-limiting step in the LCM was 18.8 kcal/mol, which is more in agreement with the available experimental value (17.8 kcal/mol), indicating that LCM could significantly accelerate the rate of AM, because it has an energy barrier ~2 times lower than that of the NCM. Interestingly, we also found that the catalytic triad (Asp-His-Ser) of the lipase and water could effectively drop the reaction barrier, which served as the general acid or base, or shuttle of the proton. View Full-Text
Keywords: acyl migration; density functional theory; lipase-catalyzed mechanism; structural triglycerides; QM acyl migration; density functional theory; lipase-catalyzed mechanism; structural triglycerides; QM
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Mao, J.; Hu, Z.; Hu, J.; Zhu, X.; Xiong, H. A Density Functional Theory (DFT) Study of the Acyl Migration Occurring during Lipase-Catalyzed Transesterifications. Int. J. Mol. Sci. 2019, 20, 3438.

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