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工程化脂肪酸光脱羧酶以实现反式脂肪酸的高选择性脱羧。

Engineering Fatty Acid Photodecarboxylase to Enable Highly Selective Decarboxylation of trans Fatty Acids.

机构信息

Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.

Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, China.

出版信息

Angew Chem Int Ed Engl. 2021 Sep 13;60(38):20695-20699. doi: 10.1002/anie.202107694. Epub 2021 Aug 15.

Abstract

Due to the high risk of heart disease caused by the intake of trans fatty acids, a method to eliminate trans fatty acids from foods has become a critical issue. Herein, we engineered fatty acid photo-decarboxylase from Chlorella variabilis (CvFAP) to selectively catalyze the decarboxylation of trans fatty acids to yield readily-removed hydrocarbons and carbon dioxide, while cis fatty acids remained unchanged. An efficient protein engineering based on FRISM strategy was implemented to intensify the electronic interaction between the residues and the double bond of the substrate that stabilized the binding of elaidic acid in the channel. For the model compounds, oleic acid and elaidic acid, the best mutant, V453E, showed a one-thousand-fold improvement in the trans-over-cis (ToC) selectivity compared with wild type (WT). As the first report of the direct biocatalytic decarboxylation resolution of trans/cis fatty acids, this work offers a safe, facile, and eco-friendly process to eliminate trans fatty acids from edible oils.

摘要

由于摄入反式脂肪酸会导致心脏病的风险很高,因此消除食物中反式脂肪酸的方法已成为一个关键问题。在此,我们从栅藻(Chlorella variabilis)中工程化脂肪酸光脱羧酶(CvFAP),以选择性地催化反式脂肪酸脱羧生成易于去除的烃类和二氧化碳,而顺式脂肪酸保持不变。通过基于 FRISM 策略的有效蛋白质工程,增强了残基与底物双键之间的电子相互作用,从而稳定了通道中反式油酸的结合。对于模型化合物油酸和反式油酸,最佳突变体 V453E 与野生型相比,对反式-顺式(ToC)的选择性提高了一千倍。作为直接生物催化反式/顺式脂肪酸脱羧拆分的首例报道,该工作为从食用油中消除反式脂肪酸提供了一种安全、简便、环保的方法。

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