An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid

doi:10.1016/j.cjche.2020.06.013

中国化学工程学报 ›› 2021, Vol. 32 ›› Issue (4): 315-323.DOI: 10.1016/j.cjche.2020.06.013

• Biotechnology and Bioengineering • 上一篇下一篇

An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid

Haiyan Zhou, Yizuo Li, Rui Jiang, Xianlin Wang, Yuanshan Wang, Yaping Xue, Yuguo Zheng

Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, China;Engineering Research Center of Bioconversion and Biopurification of Ministry of Education, Zhejiang University of Technology, Hangzhou 310014, China;The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals, Zhejiang University of Technology, Hangzhou 310014, China

收稿日期:2020-02-17 修回日期:2020-05-14 出版日期:2021-04-28 发布日期:2021-06-19
通讯作者: Yaping Xue

An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid

Haiyan Zhou, Yizuo Li, Rui Jiang, Xianlin Wang, Yuanshan Wang, Yaping Xue, Yuguo Zheng

Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou 310014, China;Engineering Research Center of Bioconversion and Biopurification of Ministry of Education, Zhejiang University of Technology, Hangzhou 310014, China;The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals, Zhejiang University of Technology, Hangzhou 310014, China

Received:2020-02-17 Revised:2020-05-14 Online:2021-04-28 Published:2021-06-19
Contact: Yaping Xue

摘要/Abstract

摘要： R-2-(4-hydroxyphenoxy)propionic acid (R-HPPA) is a key intermediate for the synthesis of classic herbicides with high selectivity against grassy weed. The main route for R-HPPA biosynthesis is to hydroxylate the substrate R-2-phenoxypropionic acid (R-PPA) at C-4 position with microbes. In order to provide sufficient R-PPA for the industrial production of R-HPPA, an effective R-PPA synthesis method was established and optimized in this work. The synthesis process mainly consisted of two steps:(1) synthesis of S-2-chloropropionic acid from L-alanine via diazotization and chlorination reactions; and (2) synthesis of R-PPA from S-2-chloropropionic acid and phenol via etherification reaction. The optimal reaction conditions were as follows:HCl:NaNO₂:KI:L-Ala=2.0:1.2:0.7:1.0 (in molar), 125℃ reflux for 1.5 h, with KI as catalyst, and KI:S-2-chloropropionic acid:phenol=0.075:1.2:1.0 (in molar). Under these conditions, an improved molar conversion rate (74.9%, calculated in phenol) was achieved. After extraction using anionic exchange resin Amberlite IRA-400 (CI), R-PPA product with a purity of 95.08% was obtained. The purified R-PPA was identified and evaluated in the application of the biotransformative production of R-HPPA. The results indicated that the synthesized R-PPA supported the R-HPPA biosynthesis with a comparable yield as that of the standard R-PPA. The R-PPA synthesis method provided herein exhibited the advantages of low price and easy availability of raw materials, less toxicity of reagents, simple manipulations, and low equipment/instrument requirements.

关键词: R-2-phenoxypropionic acid, R-2-(4-hydroxyphenoxy)propionic acid, Biosynthesis, S-2-chloropropionic acid

Abstract: R-2-(4-hydroxyphenoxy)propionic acid (R-HPPA) is a key intermediate for the synthesis of classic herbicides with high selectivity against grassy weed. The main route for R-HPPA biosynthesis is to hydroxylate the substrate R-2-phenoxypropionic acid (R-PPA) at C-4 position with microbes. In order to provide sufficient R-PPA for the industrial production of R-HPPA, an effective R-PPA synthesis method was established and optimized in this work. The synthesis process mainly consisted of two steps:(1) synthesis of S-2-chloropropionic acid from L-alanine via diazotization and chlorination reactions; and (2) synthesis of R-PPA from S-2-chloropropionic acid and phenol via etherification reaction. The optimal reaction conditions were as follows:HCl:NaNO₂:KI:L-Ala=2.0:1.2:0.7:1.0 (in molar), 125℃ reflux for 1.5 h, with KI as catalyst, and KI:S-2-chloropropionic acid:phenol=0.075:1.2:1.0 (in molar). Under these conditions, an improved molar conversion rate (74.9%, calculated in phenol) was achieved. After extraction using anionic exchange resin Amberlite IRA-400 (CI), R-PPA product with a purity of 95.08% was obtained. The purified R-PPA was identified and evaluated in the application of the biotransformative production of R-HPPA. The results indicated that the synthesized R-PPA supported the R-HPPA biosynthesis with a comparable yield as that of the standard R-PPA. The R-PPA synthesis method provided herein exhibited the advantages of low price and easy availability of raw materials, less toxicity of reagents, simple manipulations, and low equipment/instrument requirements.

Key words: R-2-phenoxypropionic acid, R-2-(4-hydroxyphenoxy)propionic acid, Biosynthesis, S-2-chloropropionic acid

Haiyan Zhou, Yizuo Li, Rui Jiang, Xianlin Wang, Yuanshan Wang, Yaping Xue, Yuguo Zheng. An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid[J]. 中国化学工程学报, 2021, 32(4): 315-323.

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An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid

An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid

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