School of Marine Sciences, Sun Yat-Sen University, Zhuhai, 519082, P. R. China.
Southern Marine Science and Engineering Guangdong Laboratory (Zhuhai), Zhuhai, 519082, P. R. China.
ChemistryOpen. 2021 May;10(5):553-559. doi: 10.1002/open.202100039.
Photodecarboxylase from Chlorella variabillis (CvFAP) is one of the three known light-activated enzymes that catalyzes the decarboxylation of fatty acids into the corresponding C1-shortened alkanes. Although the substrate scope of CvFAP has been altered by protein engineering and decoy molecules, it is still limited to mono-fatty acids. Our studies demonstrate for the first time that long chain dicarboxylic acids can be converted by CvFAP. Notably, the conversion of dicarboxylic acids to alkanes still represents a chemically very challenging reaction. Herein, the light-driven enzymatic decarboxylation of dicarboxylic acids to the corresponding (C2-shortened) alkanes using CvFAP is described. A series of dicarboxylic acids is decarboxylated into alkanes in good yields by means of this approach, even for the preparative scales. Reaction pathway studies show that mono-fatty acids are formed as the intermediate products before the final release of C2-shortened alkanes. In addition, the thermostability, storage stability, and recyclability of CvFAP for decarboxylation of dicarboxylic acids are well evaluated. These results represent an advancement over the current state-of-the-art.
变应性小球藻光脱羧酶（CvFAP）是已知的三种光激活酶之一，可催化脂肪酸脱羧生成相应的 C1-短链烷烃。尽管通过蛋白质工程和诱饵分子改变了 CvFAP 的底物范围，但它仍然仅限于单脂肪酸。我们的研究首次证明 CvFAP 可以转化长链二羧酸。值得注意的是，二羧酸转化为烷烃仍然是一个具有挑战性的化学反应。本文描述了使用 CvFAP 进行二羧酸的光驱动酶促脱羧反应，生成相应的（C2-短链）烷烃。通过这种方法，即使是在制备规模下，一系列二羧酸也可以高产率地转化为烷烃。反应途径研究表明，在最终释放 C2-短链烷烃之前，单脂肪酸先形成中间体产物。此外，还对 CvFAP 用于二羧酸脱羧的热稳定性、储存稳定性和可回收性进行了全面评估。这些结果代表了现有技术的进步。
