128994-26-3Relevant articles and documents
Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide
Maeda, Chihiro,Mitsuzane, Mayato,Ema, Tadashi
supporting information, p. 1853 - 1856 (2019/03/11)
Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO2. Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.
Directed evolution of an enantioselective epoxide hydrolase: Uncovering the source of enantioselectivity at each evolutionary stage
Reetz, Manfred T.,Bocola, Marco,Wang, Li-Wen,Sanchis, Joaquin,Cronin, Annette,et al.
supporting information; experimental part, p. 7334 - 7343 (2009/10/17)
Directed evolution of enzymes as enantioselective catalysts in organic chemistry is an alternative to traditional asymmetric catalysis using chiral transition-metal complexes or organocatalysts, the different approaches often being complementary. Moreover, directed evolution studies allow us to learn more about how enzymes perform mechanistically. The present study concerns a previously evolved highly enantioselective mutant of the epoxide hydrolase from Aspergillus niger in the hydrolytic kinetic resolution of racemic glycidyl phenyl ether. Kinetic data, molecular dynamics calculations, molecular modeling, inhibition experiments, and X-raystructural work for the wild-type (WT) enzyme and the best mutant revea l the basis of the large increase in enantioselectivity (E = 4.6 versus E = 115). The overall structures of the WT and the mutant are essentially identical, but dramatic differences are observed in the active site asrevealed by the X-ray structures. All of the experimental and computati onal results support a model in which productive positioning of the preferred (S)-glycidyl phenyl ether, but not the (R)-enantiomer, forms the basis of enhanced enantioselectivity. Predictions regarding substrate scope and enantioselectivity of the best mutant are shown to be possible.
Studies on agents with vasodilator and β-blocking activities. III synthesis and activity of optical isomers of TZC-1370
Seki,Takezaki,Ohuchi,Saitoh,Ishimori,Yasuda
, p. 1719 - 1723 (2007/10/03)
Optical isomers of TZC-1370 (1) were prepared from (R)- and (S)-1-(2- chlorophenoxy)-2,3-epoxypropane. When given intravenously to anesthetized rats, the (S)-isomer was about 40 times more potent in terms of β-blocking activity than the (R)-isomer, while
