32313-84-1Relevant academic research and scientific papers
BVMO-catalysed dynamic kinetic resolution of racemic benzyl ketones in the presence of anion exchange resins
Rodriguez, Cristina,De Gonzalo, Gonzalo,Rioz-Martinez, Ana,Torres Pazmino, Daniel E.,Fraaije, Marco W.,Gotor, Vicente
body text, p. 1121 - 1125 (2010/06/20)
4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB was employed in the presence of a weak anion exchange resin to perform dynamic kinetic resolutions of racemic benzyl ketones with high conversions and good optical purities. Different parameters that affect to the efficiency of the enzymatic Baeyer-Villiger oxidation and racemisation were analyzed in order to optimize the activity and selectivity of the biocatalytic system. The Royal Society of Chemistry.
Ionic liquids for enhancing the enantioselectivity of isolated BVMO-catalysed oxidations
Rodriguez, Cristina,De Gonzalo, Gonzalo,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 2255 - 2260 (2011/02/24)
The present study describes the first-time usage of an isolated thermostable Baeyer-Villiger monooxygenase (phenylacetone monooxygenase, PAMO) in the presence of ionic liquids. The stability, activity and selectivity of PAMO as an oxidative enzyme in the presence of different ionic liquids were studied. This revealed that the addition of some specific ionic liquids, such Ammoeng 102 and [bmim]MeSO4, can significantly enhance the E-value in the oxidation of racemic benzylketones. Moreover, the use of ionic liquids increases the optimal substrate concentration for performing Baeyer-Villiger oxidation, thereby extending the biocatalytic repertoire of PAMO for synthetic applications.
Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
Rodriguez, Cristina,Gonzalo, Gonzalo de,Torres Pazmino, Daniel E.,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 1168 - 1173 (2009/10/02)
The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic α-alkyl benzylketones with longer alkyl chains as well as with two substituted α-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis.
Immobilized Manihot esculenta preparation as a novel biocatalyst in the enantioselective acetylation of racemic alcohols
Machado, Luciana L.,Lemos, Telma L.G.,de Mattos, Marcos Carlos,de Oliveira, Maria da Conceicao F.,de Gonzalo, Gonzalo,Gotor-Fernandez, Vicente,Gotor, Vicente
, p. 1418 - 1423 (2008/12/20)
The enzymatic preparation obtained from a discard of Manihot esculenta roots has been successfully immobilized on calcium alginate hydrogels. This preparation has been tested as a chiral biocatalyst in the enzymatic acylation of a set of racemic aromatic alcohols. Depending on the reaction conditions, excellent enantioselectivities can be achieved. Some parameters that can alter the biocatalytic properties of the enzyme, such as solvent, temperature, acyl donor and substrate structure have been studied exhaustively in order to establish a deeper knowledge of this novel biocatalyst.
Solvolysis of 1-Arylethyl Tosylates. Kinetic and Stereochemical Tests for Solvent Participation
Allen, Anette D.,Kanagasabapathy, V. M.,Tidwell, Thomas T.
, p. 4513 - 4519 (2007/10/02)
Solvolytic studies of the 1-arylethyl tosylates 8a (Ar=3-BrC6H4), 8b (Ar=3-CF3C6H4), and 8c (Ar=3,5-(CF3)2C6H3) show that in relatively nonnucleophilic solvents all three substrates have polarimetric rates markedly faster than rates of product formation.These products are largely racemic, but solvolysis of 8c in CF3CO2H gives 6percent net retention.In the more nucleophilic solvents the rates of product formation are close to the polarimetric rates and the products show extensive inversion of configuration.The results are interpreted in terms of an ion-pair mechanism in which nucleophilic solvent attack on the ion pair plays a major role.In the less nucleophilic solvents this attack is rate limiting, whereas attack of the more nucleophilic solvents is fast and initial ionization is rate limiting.Direct displacement by the solvent could contribute to the reactions in the more nucleophilic solvents but is not required by any of the results.The ion-pair mechanism provides a single consistent explanation for the results in all the solvents with all the substrates, and also readily accommodates a variety of other results in the literature, particularly the findings of oxygen and deuterium scrambling, and elimination during solvolysis.
