33028-97-6Relevant articles and documents
Reshaping the active pocket of esterase Est816 for resolution of economically important racemates
Fan, Xinjiong,Fu, Yao,Liu, Xiaolong,Zhao, Meng
, p. 6126 - 6133 (2021/09/28)
Bacterial esterases are potential biocatalysts for the production of optically pure compounds. However, the substrate promiscuity and chiral selectivity of esterases usually have a negative correlation, which limits their commercial value. Herein, an efficient and versatile esterase (Est816) was identified as a promising catalyst for the hydrolysis of a wide range of economically important substrates with low enantioselectivity. We rationally designed several variants with up to 11-fold increased catalytic efficiency towards ethyl 2-arylpropionates, mostly retaining the initial substrate scope and enantioselectivity. These variants provided a dramatic increase in efficiency for biocatalytic applications. Based on the best variant Est816-M1, several variants with higher or inverted enantioselectivity were designed through careful analysis of the structural information and molecular docking. Two stereoselectively complementary mutants, Est816-M3 and Est816-M4, successfully overcame and even reversed the low enantioselectivity, and several 2-arylpropionic acid derivatives with highEvalues were obtained. Our results offer potential industrial biocatalysts for the preparation of structurally diverse chiral carboxylic acids and further lay the foundation for improving the catalytic efficiency and enantioselectivity of esterases.
Alpha-alkylphenylacetic acid compound with high optical activity as well as preparation method and application thereof
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Paragraph 0060-0063, (2020/09/16)
The invention discloses an alpha-alkylphenylacetic acid compound with high optical activity as well as a preparation method and application of the alpha-alkylphenylacetic acid compound. The preparation method comprises the following steps: mixing an aryl alkyl substituted malonic acid monoester substrate and a sulfonamide organic catalyst derived from chiral cyclohexylenediamine according to a molar ratio of 1: (0.01-0.30) in an organic solvent, and reacting for 2-48 hours at the temperature of 20-50 DEG C to obtain the alpha-alkylphenylacetic acid compound. The alpha-alkylphenylacetic acid compound can be used for preparing non-steroidal anti-inflammatory drugs, analgesics and central nervous excitants. The preparation method has the advantages of simple operation, mild conditions, almostno by-product, easily available catalyst and high enantioselectivity, and the reaction product can be used for synthesizing medical intermediates with important biological activity through simple conversion.
Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol
Mandrelli, Francesca,Blond, Aurélie,James, Thomas,Kim, Hyejin,List, Benjamin
, p. 11479 - 11482 (2019/07/18)
We report a highly enantioselective catalytic protonation of bis-silyl ketene acetals. Our method delivers α-branched carboxylic acids, including nonsteroidal anti-inflammatory arylpropionic acids such as Ibuprofen, in high enantiomeric purity and high yields. The process can be incorporated in an overall deracemization of α-branched carboxylic acids, involving a double deprotonation and silylation followed by the catalytic asymmetric protonation.