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

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

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

Biotechnology and Bioengineering | Updated：2026-01-06

- An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid
- Chinese Journal of Chemical Engineering Vol. 32, Issue 4, Pages: 315-323(2021)
- Affiliations：
  
  1. Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology,Hangzhou,China,310014
  2. Engineering Research Center of Bioconversion and Biopurification of Ministry of Education, Zhejiang University of Technology,Hangzhou,China,310014
  3. The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals, Zhejiang University of Technology,Hangzhou,China,310014
- Author bio：
- Funds：
- DOI：
  CLC：
- Published：2021
- Accepted：
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摘要

Abstract

-2-(4-hydroxyphenoxy)propionic acid (

-HPPA) is a key intermediate for the synthesis of classic herbicides with high selectivity against grassy weed. The main route for

-HPPA biosynthesis is to hydroxylate the substrate

-2-phenoxypropionic acid (

-PPA) at C-4 position with microbes. In order to provide sufficient

-PPA for the industrial production of

-HPPA

an effective

-PPA synthesis method was established and optimized in this work. The synthesis process mainly consisted of two steps:(1) synthesis of

-2-chloropropionic acid from L-alanine

via

diazotization and chlorination reactions; and (2) synthesis of

-PPA from

-2-chloropropionic acid and phenol

via

etherification reaction. The optimal reaction conditions were as follows:HCl:NaNO

: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:

-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 Ambe

rlite IRA-400 (CI)

-PPA product with a purity of 95.08% was obtained. The purified

-PPA was identified and evaluated in the application of the biotransformative production of

-HPPA. The results indicated that the synthesized

-PPA supported the

-HPPA biosynthesis with a comparable yield as that of the standard

-PPA. The

-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.

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

DOI：

摘要

Abstract

关键词

Keywords

references