84890-25-5Relevant articles and documents
Enzymatic resolution of naproxen
Koul, Surrinder,Parshad, Rajinder,Taneja, Subhash C.,Qazi, Ghulam N.
, p. 2459 - 2465 (2003)
Trichosporon sp. (TSL), a newly found strain isolated from a locally fermented cottage cheese has been found to be highly stereoselective in the resolution of (S)-(+)-naproxen (ee >99%, E～500) from the corresponding racemic methyl ester. The process of resolution using whole cells has been scaled up to multi-kg level. Optimization of experimental conditions including downstream processing at 80-100 g/L substrate concentration with >90% recovery has been achieved. Changes in the physical parameters such as the particle size of the substrate play an important role in the resolution kinetics. A new strain of Trichosporon sp. having high cell density in cultivation (>60 g dry cell mass L-1 in 14-16 h) is found to be sufficiently stable for two years in dry powder form at 5-8°C. The viability of the resolution process has been further improved by the development of a simple racemization process for the enriched (R)-(-)-ester.
Reshaping the active pocket of esterase Est816 for resolution of economically important racemates
Liu, Xiaolong,Zhao, Meng,Fan, Xinjiong,Fu, Yao
, 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.
Design, synthesis and QSAR studies on a series of 2, 5-disubstituted-1,3,4-oxadiazole derivatives of diclofenac and naproxen for analgesic and anti-inflammatory activity
Ilango, Kaliappan,Valentina, Parthiban,Kumar, Gajendra,Dixit, Dushyant,Nilewar, Shrikant,Kathiravan, Muthu K.
, p. 753 - 763 (2015/12/01)
A series of twenty molecules belonging to 2, 5-disubstituted-1, 3, 4-oxadiazole derivatives of Diclofenac and Naproxen were designed, synthesized and their structures were confirmed by spectroscopy. The target compounds were evaluated for anti-inflammator
