158896-00-5Relevant articles and documents
The Stereoselective Oxidation of para-Substituted Benzenes by a Cytochrome P450 Biocatalyst
Chao, Rebecca R.,Lau, Ian C.-K.,Coleman, Tom,Churchman, Luke R.,Child, Stella A.,Lee, Joel H. Z.,Bruning, John B.,De Voss, James J.,Bell, Stephen G.
, p. 14765 - 14777 (2021/09/14)
The serine 244 to aspartate (S244D) variant of the cytochrome P450 enzyme CYP199A4 was used to expand its substrate range beyond benzoic acids. Substrates, in which the carboxylate group of the benzoic acid moiety is replaced were oxidised with high activity by the S244D mutant (product formation rates >60 nmol.(nmol-CYP)?1.min?1) and with total turnover numbers of up to 20,000. Ethyl α-hydroxylation was more rapid than methyl oxidation, styrene epoxidation and S-oxidation. The S244D mutant catalysed the ethyl hydroxylation, epoxidation and sulfoxidation reactions with an excess of one stereoisomer (in some instances up to >98 %). The crystal structure of 4-methoxybenzoic acid-bound CYP199A4 S244D showed that the active site architecture and the substrate orientation were similar to that of the WT enzyme. Overall, this work demonstrates that CYP199A4 can catalyse the stereoselective hydroxylation, epoxidation or sulfoxidation of substituted benzene substrates under mild conditions resulting in more sustainable transformations using this heme monooxygenase enzyme.
HPLC enantioseparation on a homochiral MOF-silica composite as a novel chiral stationary phase
Tanaka, Koichi,Muraoka, Toshihide,Otubo, Yasuhiro,Takahashi, Hiroki,Ohnishi, Atsushi
, p. 21293 - 21301 (2016/03/08)
The last frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal-organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers of various kinds of racemic sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides. The experimental results showed excellent performances for enantioseparation, and highlighted that enantioseparation on homochiral MOF columns is practical.
Flavin-cyclodextrin conjugates as catalysts of enantioselective sulfoxidations with hydrogen peroxide in aqueous media
Mojr, Viktor,Herzig, Vladimir,Budisnsky, Milo,Cibulka, Radek,Kraus, Tomas
supporting information; experimental part, p. 7599 - 7601 (2010/12/18)
β-Cyclodextrin-flavin conjugates are highly efficient catalysts for the sulfoxidation of methyl phenyl sulfides with hydrogen peroxide in neat aqueous media operating at loadings down to 0.2 mol% and allowing for enantioselectivities up to 80% ee.
