Yeasts as biocatalysts in the stereoselective reduction of acetophnone

Fil: Decarlini, M. F. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Manzoni, C. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Medici, E. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Vazquez, A. M. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Aimar, M. L. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química. Cátedra de Química Aplicada; Argentina.The asymmetric reduction of prochiral ketones represents a pivotal transformation for the production of chiral alcohols. Several of them are considered as key starting materials in obtaining of pharmaceuticals. Nowadays, bio-reductions are an important component of organic synthesis for the production of drugs. In this sense, microorganisms are considered an outstanding tool for the obtaining of these chiral building blocksFil: Decarlini, M. F. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Manzoni, C. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Medici, E. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Vazquez, A. M. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Aimar, M. L. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química. Cátedra de Química Aplicada; Argentina.Otras Ciencias Química

Screening of some Ascomycetes and Basidiomycetes species for the production of 1- phenylethanol enantiomerically pure

Fil: Decarlini, M. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Colavolpe, B. Instituto Tecnológico de Chascomús. Instituto de Investigaciones Biotecnológicas. Laboratorio de Micología y Cultivo de Hongos Comestibles; Argentina.Fil: Albertó, E. Instituto Tecnológico de Chascomús. Instituto de Investigaciones Biotecnológicas. Laboratorio de Micología y Cultivo de Hongos Comestibles; Argentina.Fil: Vázquez, A. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Aimar, L. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química. Cátedra de Química Aplicada; Argentina.The asymmetric reduction of prochiral ketones represents a pivotal transformation for the production of chiral alcohols. Several of them are considered as key starting materials in obtaining pharmaceuticals.Fil: Decarlini, M. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Colavolpe, B. Instituto Tecnológico de Chascomús. Instituto de Investigaciones Biotecnológicas. Laboratorio de Micología y Cultivo de Hongos Comestibles; Argentina.Fil: Albertó, E. Instituto Tecnológico de Chascomús. Instituto de Investigaciones Biotecnológicas. Laboratorio de Micología y Cultivo de Hongos Comestibles; Argentina.Fil: Vázquez, A. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Aimar, L. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química. Cátedra de Química Aplicada; Argentina.Otras Ciencias Química

Bio-reduccion estereoselectiva de acetofenona a (+)-(R)-1-Feniletanol catalizada por especies del genero Candida

Fil: Decarlini, M. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Aimar, M. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química. Cátedra de Química Aplicada; Argentina.Fil: Vázquez, A. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Rustán, M. Universidad Nacional de Córdoba; Argentina.Fil: Peralta, N. Universidad Nacional de Córdoba; Argentina.Fil: Mattos, M. Universidad Nacional de Córdoba; Argentina.La reducción estereoselectiva de cetonas proquirales es una de las reacciones más importantes de la Química Orgánica. Mediante estas transformaciones es posible la obtención de alcoholes enantioméricamente puros los cuales son precursores claves en la síntesis de diferentes compuestos de interés farmacéutico. Una de las formas preferidas de realizar esta transformación es a través de la utilización de procesos biocatalíticos empleando para ello diversos microorganismos. Estos sistemas biocatalíticos tienen la ventaja de ser ambientalmente amigables comparados a los métodos clásicos de síntesis que en general utilizan metales pesados, auxiliares quirales y solventes orgánicos bajo atmosfera de hidrogeno.http://microbiologia2014.com.ar/website/Fil: Decarlini, M. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Aimar, M. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química. Cátedra de Química Aplicada; Argentina.Fil: Vázquez, A. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina.Fil: Rustán, M. Universidad Nacional de Córdoba; Argentina.Fil: Peralta, N. Universidad Nacional de Córdoba; Argentina.Fil: Mattos, M. Universidad Nacional de Córdoba; Argentina.Otras Ciencias Química

Kinetic profiles of the stereoselective reduction of acetophenone and its derivatives promoted by Galactomyces candidus GZ1. A mechanistic interpretation

A mechanistic interpretation of the kinetic profiles obtained for the stereoselective reduction of acetophenone promoted by Galactomyces candidus GZ1 under aerobic and anaerobic conditions was made. Based on experimental and bibliographical data, a mechanism which may involve the participation of two alcohol dehydrogenases with opposite stereoselectivities and alcohol oxidase is discussed. Due to the stereoselectivity of the reduction of acetophenone being changed when anaerobic conditions were used, this microorganism also permitted (S)-1-phenylethanol to be obtained in the absence of oxygen. Moreover, the kinetic profiles of the reactions of a racemic mixture of (R,S)-1-phenylethanol and pure (S)-1-phenylethanol with Gal. candidus were analyzed, which corroborated that there existed a reaction step where (S)-1-phenylethanol was oxidized to acetophenone. The results presented here show that not only is it possible to resolve racemic mixtures of phenylethanols when Gal. candidus is used as a biocatalyst, but that this is also efficient in causing the complete stereoinversion of pure (S)-1-phenylethanol to (R)-1-phenylethanol.Fil: Decarlini, Maria Florencia. Universidad Católica de Córdoba; ArgentinaFil: Bordon, Daniela Laura. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Vázquez, Ana M.. Universidad Católica de Córdoba; ArgentinaFil: Demmel, Gabriela Ines. Universidad Católica de Córdoba; ArgentinaFil: Rossi, Laura Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Aimar, Mario Leandro. Universidad Nacional de Córdoba; Argentin

Blood pressure-lowering effects of nifedipine/candesartan combinations in high-risk individuals: Subgroup analysis of the DISTINCT randomised trial

The DISTINCT study (reDefining Intervention with Studies Testing Innovative Nifedipine GITS - Candesartan Therapy) investigated the efficacy and safety of nifedipine GITS/candesartan cilexetil combinations vs respective monotherapies and placebo in patients with hypertension. This descriptive sub-analysis examined blood pressure (BP)-lowering effects in high-risk participants, including those with renal impairment (estimated glomerular filtration rate<90 ml min-1, n=422), type 2 diabetes mellitus (n=202), hypercholesterolaemia (n=206) and cardiovascular (CV) risk factors (n=971), as well as the impact of gender, age and body mass index (BMI). Participants with grade I/II hypertension were randomised to treatment with nifedipine GITS (N) 20, 30, 60 mg and/or candesartan cilexetil (C) 4, 8, 16, 32 mg or placebo for 8 weeks. Mean systolic BP and diastolic BP reductions after treatment in high-risk participants were greater, overall, with N/C combinations vs respective monotherapies or placebo, with indicators of a dose-response effect. Highest rates of BP control (ESH/ESC 2013 guideline criteria) were also achieved with highest doses of N/C combinations in each high-risk subgroup. The benefits of combination therapy vs monotherapy were additionally observed in patient subgroups categorised by gender, age or BMI. All high-risk participants reported fewer vasodilatory adverse events in the pooled N/C combination therapy than the N monotherapy group. In conclusion, consistent with the DISTINCT main study outcomes, high-risk participants showed greater reductions in BP and higher control rates with N/C combinations compared with respective monotherapies and lesser vasodilatory side-effects compared with N monotherapy

Optimisation of the bioreduction process of carbonyl compounds promoted by seeds of glossy privet (Ligustrum lucidum - Oleaceae) and its application to the synthesis of key intermediates

The fruits of Ligustrum lucidum were used as an efficient biological reducer of carbonyl compounds, and trials were carried out to optimise the reductive process using acetophenone as the model substrate. In order to try to eliminate the dependence on the seasonal production of the fruits, a study was carried out to find ways to conserve them. The results reported here show that it is possible to store the dehydrated fruits of glossy privet at room temperature over a prolonged period of time, during which time they can be used as a common chemical reagent. On the other hand, studies performed on different parts of the fruits established that the seeds are responsible for the bioreduction process, with the best reduction conditions found being isolated seeds from the fruits of glossy privet at 25 °C, in a 100 mM phosphate buffer pH 6.0, using 0.67% w/v of DMSO as co-solvent with an acetophenone charge of 2.67 g/L (22 mM). Moreover, seed reuse studies showed that it is possible to recycle them, providing almost the same activity and enantioselectivity from the first to the fifth cycle, without any loss of biocatalytic properties. Finally, using whole seeds of glossy privet in optimal reaction conditions, important alcohols useful as key intermediates in the synthesis of industrial products were obtained on a laboratory scale through the reduction of specially selected ketones and aldehydes.Fil: Bordon, Daniela Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Vázquez, Ana M.. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; ArgentinaFil: Decarlini, Maria Florencia. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; ArgentinaFil: Demmel, Gabriela Ines. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; ArgentinaFil: Rossi, Laura Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Aimar, Mario Leandro. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentin

Fungi isolated from food samples for an efficient stereoselective production of phenylethanols

Twenty strains of fungi isolated from food samples were screened for the asymmetric reduction of acetophenone. A dimorphic fungus denominated initially as GZ1 and isolated from a carrot sour rot showed very high reduction activities, and based on phenotypic and genetic characteristics was identified as Galactomyces candidus. The only product of the reduction was confirmed to be (R)-1-phenylethanol. The bioreduction conditions mediated by Gal. candidus GZ1 were investigated, and the optimal conditions in terms of acetophenone concentration, temperature, pH media, co-solvent, the charge of inoculum and shaking speed were established. Under the optimal conditions of 1.875 g/L of acetophenone dissolved in DMSO (1.25% v/v), 112.5 g/L of microorganism cells in 100 mM sterile phosphate buffer solution at pH 7.0, 25 °C and 150 rpm, the conversion and enantiomeric excess values after 48 h reaction were 99% and > 99.9%, respectively. A preparative scale reaction of (R)-1-phenylethanol was made and the isolated yield was 82% with > 99.9 e.e.%. Additionally, a study using several substituted acetophenones was carried out, and the advantages and scope of GZ1 in the production of chiral 1-phenylethanols were established. In this sense, good results were obtained with 3′-hydroxyacetophenone and a preparative scale reaction was performed which give (R)-1-(3′-hydroxyphenyl)ethanol (key intermediate of Rivastigmine) with 53% of isolated yield and > 99.9 e.e.%.Fil: Decarlini, Maria Florencia. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; ArgentinaFil: Aimar, Mario Leandro. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; ArgentinaFil: Vázquez, Ana M.. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; ArgentinaFil: Vero, Silvana. Universidad de la República; UruguayFil: Rossi, Laura Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Yang, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Area de Ciencias Agrarias, Ingeniería, Ciencias Biológicas y de la Salud de la Universidad Católica de Córdoba; Argentin