期刊
ACS CATALYSIS
卷 11, 期 5, 页码 2808-2818出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c04961
关键词
2-hydroxyacetophenone; spontaneous chemical reaction; pyruvate decarboxylase; glyoxylic acid; (S)-1-phenyl-1; 2-ethanediol
资金
- National Natural Science Foundation of China [22038005, 22008089, 32021005]
- National Key R&D Program of China [2018YFA0901400]
- national first-class discipline program of Light Industry Technology and Engineering [LITE2018-08]
A one-pot enzymatic-chemical cascade route was developed to synthesize 2-Hydroxyacetophenone (2-HAP) with a final yield of 92.7%. The introduction of stereospecific carbonyl reductases allowed for further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method shows potential for synthesizing other valuable chemicals by cascading spontaneous chemical and enzymatic reactions.
2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C-C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic-chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.
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