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模块化级联生物催化高效合成苯乙酸酯和2-苯乙醇

Efficient Synthesis of Phenylacetate and 2-Phenylethanol by Modular Cascade Biocatalysis.

作者信息

Mao Zuoxi, Liu Lijun, Zhang Yang, Yuan Jifeng

机构信息

State Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Fujian, 361102, P. R. China.

出版信息

Chembiochem. 2020 Sep 14;21(18):2676-2679. doi: 10.1002/cbic.202000182. Epub 2020 May 27.

DOI:10.1002/cbic.202000182
PMID:32291886
Abstract

The green and sustainable synthesis of chemicals from renewable feedstocks by a biotransformation approach has gained increasing attention in recent years. In this work, we developed enzymatic cascades to efficiently convert l-phenylalanine into 2-phenylethanol (2-PE) and phenylacetic acid (PAA), l-tyrosine into tyrosol (p-hydroxyphenylethanol, p-HPE) and p-hydroxyphenylacetic acid (p-HPAA). The enzymatic cascade was cast into an aromatic aldehyde formation module, followed by an aldehyde reduction module, or aldehyde oxidation module, to achieve one-pot biotransformation by using recombinant Escherichia coli. Biotransformation of 50 mM l-Phe produced 6.76 g/L PAA with more than 99 % conversion and 5.95 g/L of 2-PE with 97 % conversion. The bioconversion efficiencies of p-HPAA and p-HPE from l-Tyr reached to 88 and 94 %, respectively. In addition, m-fluoro-phenylalanine was further employed as an unnatural aromatic amino acid substrate to obtain m-fluoro-phenylacetic acid; >96 % conversion was achieved. Our results thus demonstrated high-yielding and potential industrial synthesis of above aromatic compounds by one-pot cascade biocatalysis.

摘要

近年来,通过生物转化方法从可再生原料绿色可持续地合成化学品受到了越来越多的关注。在这项工作中,我们开发了酶促级联反应,以有效地将L-苯丙氨酸转化为2-苯乙醇(2-PE)和苯乙酸(PAA),将L-酪氨酸转化为酪醇(对羟基苯乙醇,p-HPE)和对羟基苯乙酸(p-HPAA)。将酶促级联反应应用于芳香醛形成模块,随后是醛还原模块或醛氧化模块,以利用重组大肠杆菌实现一锅法生物转化。50 mM L-苯丙氨酸的生物转化产生了6.76 g/L的PAA,转化率超过99%,以及5.95 g/L的2-PE,转化率为97%。L-酪氨酸转化为p-HPAA和p-HPE的生物转化效率分别达到88%和94%。此外,间氟苯丙氨酸被进一步用作非天然芳香族氨基酸底物,以获得间氟苯乙酸;转化率>96%。因此,我们的结果证明了通过一锅法级联生物催化高产且具有潜在工业合成上述芳香族化合物的能力。

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