RESUMEN
Nitroalkanes underwent fast additions to a variety of structurally diverse aldehydes under the catalysis of d-aminoacylase in DMSO. The influences of reaction conditions including solvents, temperature, enzyme concentration and molar ratio of substrates were systematically investigated. Seventeen products were obtained in short time with moderate to high yields. It is the first report on hydrolase-catalyzed fast Henry reaction in organic solvent.
Asunto(s)
Aldehídos/metabolismo , Alcanos/metabolismo , Biocatálisis , Hidrolasas/metabolismo , Modelos Químicos , Nitrocompuestos/metabolismo , Solventes/metabolismo , Benzaldehídos/química , Benzaldehídos/metabolismo , Etano/análogos & derivados , Etano/química , Etano/metabolismo , Nitroparafinas/química , Nitroparafinas/metabolismo , Especificidad por SustratoRESUMEN
A zinc-dependent acylase, D-aminoacylase from Escherichia. Coli, displays a promiscuous activity to catalyze the carbon-carbon bond formation reaction of 1,3-dicarbonyl compounds to methyl vinyl ketone in organic media.
Asunto(s)
Amidohidrolasas/metabolismo , Carbono/química , Carbono/metabolismo , Compuestos Orgánicos , Zinc/metabolismo , Sitios de Unión , Catálisis , Cationes Bivalentes/química , Escherichia coli/enzimología , Metilación , Estructura Molecular , Solventes , Zinc/químicaRESUMEN
N-methylimidazole, a molecular solvent, but also, in cationic form, a component of 1-alkyl-3-methylimidazolium ([C(n)MIM]+) ionic liquids, showed promise as an additive in accelerating remarkably transesterification catalyzed by lipase acrylic resin from Candida antarctica (CAL-B).
Asunto(s)
Imidazoles/farmacología , Lipasa/metabolismo , Ribavirina/química , Ribavirina/metabolismo , Acilación/efectos de los fármacos , Aniones/química , Candida/enzimología , Catálisis/efectos de los fármacos , Líquidos Iónicos , Estructura MolecularRESUMEN
A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide ([bmIm]OH), has been introduced as a catalyst and reaction medium for the Markovnikov addition of N-heterocycles to vinyl esters under mild conditions. The evidence for the role of this basic ionic liquid [bmIm]OH in promoting the Markovnikov addition has been given. On the basis of the evidence, a mechanism was postulated.
RESUMEN
Eightfold higher yields and three times faster reaction rates were achieved by means of using a mixture solvent system composed of 90% acetone and 10% [BMIM]BF4 in the lipase-catalyzed regioselective synthesis of polymerizable ester of nucleoside drugs.
Asunto(s)
Ésteres/síntesis química , Lipasa/química , Nucleósidos/síntesis química , Compuestos Orgánicos/química , Solventes/química , Acetona/química , Boratos/química , Catálisis , Citarabina/síntesis química , Citarabina/farmacología , Esterificación , Ésteres/farmacología , Imidazoles/química , Inosina/síntesis química , Inosina/farmacología , Iones , Nucleósidos/farmacología , Ribavirina/síntesis química , Ribavirina/farmacología , Factores de TiempoRESUMEN
Enzymatic transesterification of glucose with the vinyl ester of non-steroidal anti-inflammatory drugs (NSAIDs) was in organic media performed for synthesis of novel NSAIDs-glucose conjugates. Glucose was regioselectively acylated at the 6-hydroxyl group. The indomethacin-glucose conjugate and ketoprofen-glucose conjugate were produced by the catalysis of alkaline protease from Bacillus subtilis in the respective yields of 42% (over 48 h) and 63% (over 40 h). The etodolac-glucose conjugate was obtained in 26% yield (over 144 h) by lipase from Candida antarctica.
Asunto(s)
Antiinflamatorios no Esteroideos/metabolismo , Proteínas Bacterianas/metabolismo , Endopeptidasas/metabolismo , Glucosa/metabolismo , Lipasa/metabolismo , Antiinflamatorios no Esteroideos/química , Bacillus subtilis/enzimología , Candida/enzimología , Catálisis , Cromatografía en Capa Delgada , Glucosa/química , Indometacina/química , Indometacina/metabolismo , Cetoprofeno/química , Cetoprofeno/metabolismoRESUMEN
Lipase-catalyzed synthesis of potential multifunctional ribavirin derivatives was performed in acetone. Divinyl dicarboxylates with different chain lengths (C4, C6, C9, C10) were used as acyl donors and the reactions were catalyzed by lipase immobilized on acrylic resin from Candida antarctica (CAL-B). Ribavirin was regioselectivly acylated at the primary hydroxyl groups and the corresponding vinyl esters (C4, C6, C9, C10) were prepared in respective yields of 48%, 65%, 54%, 55%.
