948997-89-5Relevant articles and documents
Titration and assignment of residues that regulate the enantioselectivity of phenylacetone monooxygenase
Zambianchi, Francesca,Fraaije, Marco W.,Carrea, Giacomo,De Gonzalo,Rodriguez, Cristina,Gotor, Vicente,Ottolina, Gianluca
, p. 1327 - 1331 (2007)
Phenylacetone monooxygense (PAMO) from Thermobifida fusca was employed for the asymmetric oxidation of thioanisole (sulfoxidation) and of racemic 2-phenylpropionaldehyde (Baeyer-Villiger oxidation). A pH dependence of enantioselectivity was observed in both cases. Two different residues, with pKa values of 7.8 ± 0.2 and 9.2 ± 0.2, appeared to be responsible for the pH effects on PAMO enantioselectivity. The protonation of Arg337 and the FAD:C4a-hydroperoxide/ FAD :C4a-peroxide equilibrium were identified as the major factors responsible for the fine-tuning of PAMO enantioselectivity in Baeyer-Villiger oxidation and sulfooxidation, respectively.
N-Heterocyclic Carbene Catalyzed Transformylation
Fernando, Jared E. M.,Levens, Alison,Moock, Daniel,Lupton, David W.
, p. 3505 - 3510 (2017/07/27)
The N-heterocyclic carbene (NHC) catalyzed transformylation has been developed for the conversion of 1°, 2°, and 3° alcohols to the corresponding formates. The reaction employs low catalyst loadings and methyl formate as the formyl transfer reagent. The scope of the reaction is broad with 23 examples reported with good yields (59-96%). The reaction is insensitive to common nitrogen and oxygen protecting groups and can be achieved in the presence of a number of heterocycles.
Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases
Rodriguez, Cristina,de Gonzalo, Gonzalo,Fraaije, Marco W.,Gotor, Vicente
, p. 1338 - 1344 (2008/02/09)
A set of racemic cyclic and linear ketones, as well as 2-phenylpropionaldehyde, were tested as substrates in the enzymatic Baeyer-Villiger oxidation catalyzed by two Baeyer-Villiger monooxygenases: phenylacetone monooxygenase (PAMO) and 4-hydroxyacetophenone monooxygenase (HAPMO). Excellent enantioselectivites (E > 200) can be obtained in the kinetic resolution processes depending on the substrate structure and the reaction conditions. The parameters affecting the biocatalytic properties of these enzymes were also studied, in order to establish a deeper understanding of these novel biocatalysts.