20714-89-0Relevant articles and documents
Highly Efficient Deracemization of Racemic 2-Hydroxy Acids in a Three-Enzyme Co-Expression System Using a Novel Ketoacid Reductase
Xue, Ya-Ping,Wang, Chuang,Wang, Di-Chen,Liu, Zhi-Qiang,Zheng, Yu-Guo
, p. 1 - 13 (2018/04/26)
Enantiopure 2-hydroxy acids (2-HAs) are important intermediates for the synthesis of pharmaceuticals and fine chemicals. Deracemization of racemic 2-HAs into the corresponding single enantiomers represents an economical and highly efficient approach for synthesizing chiral 2-HAs in industry. In this work, a novel ketoacid reductase from Leuconostoc lactis (LlKAR) with higher activity and substrate tolerance towards aromatic α-ketoacids was discovered by genome mining, and then its enzymatic properties were characterized. Accordingly, an engineered Escherichia coli (HADH-LlKAR-GDH) co-expressing 2-hydroxyacid dehydrogenase, LlKAR, and glucose dehydrogenase was constructed for efficient deracemization of racemic 2-HAs. Most of the racemic 2-HAs were deracemized to their (R)-isomers at high yields and enantiomeric purity. In the case of racemic 2-chloromandelic acid, as much as 300 mM of substrate was completely transformed into the optically pure (R)-2-chloromandelic acid (> 99% enantiomeric excess) with a high productivity of 83.8 g L?1 day?1 without addition of exogenous cofactor, which make this novel whole-cell biocatalyst more promising and competitive in practical application.
An efficient enzymatic aminolysis for kinetic resolution of aromatic α-hydroxyl acid in non-aqueous media
Chen, Shan,Liu, Fuyan,Zhang, Kuan,Huang, Hansheng,Wang, Huani,Zhou, Jiaying,Zhang, Jing,Gong, Yiwei,Zhang, Dela,Chen, Yiping,Lin, Chang,Wang, Bo
supporting information, p. 5312 - 5314 (2016/11/16)
A new and highly efficient enzymatic aminolysis approach for kinetic resolution of aromatic α-hydroxy acid in non-aqueous media has been developed. The corresponding α-hydroxyl acid ester was employed as the substrate, and commercially available Candida antarctica lipase B is used as the biocatalyst, anhydrous ammonia is the resolving agent. Reactions can be proceeded smoothly in organic solvent at ambient temperatures. High concentration of substrate is allowed due to the application of organic media and the products are obtained in yields of up to 49% with ee values of up to 99%, and with E value of >300, representing an appealing and promising protocol for large-scale preparations.
Highly enantioselective hydrogenation of aryl vinyl ketones to allylic alcohols catalyzed by the tol-binap/Dmapen ruthenium(II) complex
Arai, Noriyoshi,Azuma, Keita,Nii, Noriyuki,Ohkuma, Takeshi
supporting information; experimental part, p. 7457 - 7460 (2009/03/12)
(Chemical Equation Presented) Binap catalyst doesn't dmapen expectations: In basified 2-propanol, [RuCl2{(S)-tol-binap}{(R)-dmapen}] (1, see picture, Ar=4-CH3C6H4) catalyzes the highly enantioselective hydrogenation of a series of aryl vinyl ketones and affords the allylic alcohols in high yields with up to 98% ee. Formation of the saturated ketones and alcohols is suppressed with triphenylphosphine when necessary.