14 research outputs found
Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives
A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)- 1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenylpropan-2-one derivatives to yield chiral amines employing microbial x-transaminases, and the diastereoselective reduction of a Bischler– Napieralski imine intermediate by catalytic hydrogenation in the presence of palladium on charcoal, leading exclusively to the desired cis-isomerFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica; Argentina;Fil: Schrittwieser, Joerg H.. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria;Fil: Resch, Verena. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria;Fil: Mutti, Francesco G.. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria;Fil: Kroutil, Wolfgang. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria
Alkaloids Analysis of Habranthus cardenasianus (Amaryllidaceae), Anti-Cholinesterase Activity and Biomass Production by Propagation Strategies
Plants in the Amaryllidaceae family synthesize a diversity of bioactive alkaloids. Some of these plant species are not abundant and have a low natural multiplication rate. The aims of this work were the alkaloids analysis of a Habranthus cardenasianus bulbs extract, the evaluation of its inhibitory activity against cholinesterases, and to test several propagation strategies for biomass production. Eleven compounds were characterized by GC-MS in the alkaloid extract, which showed a relatively high proportion of tazettine. The known alkaloids tazettine, haemanthamine, and the epimer mixture haemanthidine/6-epi-haemanthidine were isolated and identified by spectroscopic methods. Inhibitory cholinesterases activity was not detected. Three forms of propagation were performed: bulb propagation from seed, cut-induced bulb division, and micropropagated bulbs. Finally, different imbibition and post-collection times were evaluated in seed germination assays. The best propagation method was cut-induced bulb division with longitudinal cuts into quarters (T1) while the best conditions for seed germination were 0-day of post-collection and two days of imbibition. The alkaloids analyses of the H. cardenasianus bulbs showed that they are a source of anti-tumoral alkaloids, especially pretazettine (tazettine) and T1 is a sustainable strategy for its propagation and domestication to produce bioactive alkaloids.Fil: Zaragoza Puchol, JosĂ© Daniel. Universidad Nacional de San Juan; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Juan; ArgentinaFil: Ortiz, Javier Esteban. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Juan; Argentina. Universidad Nacional de San Juan; ArgentinaFil: Orden, Alejandro Agustin. Universidad Nacional de San Luis; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Sánchez, Marianela. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; ArgentinaFil: Palermo, Jorge Alejandro. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas; ArgentinaFil: Tapia, AnĂbal Alejandro. Universidad Nacional de San Juan; ArgentinaFil: Bastida, Jaume. Universidad de Barcelona. Facultad de Farmacia; EspañaFil: Feresin, Gabriela Egly. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Juan; Argentina. Universidad Nacional de San Juan; Argentin
Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of Rhodotorula mucilaginosa LSL to stereoselectively reduce prochiral ketones coupled to copper(I)-catalyzed azide-alkyne cycloaddition was exploited. The reactions were performed in aqueous medium and at room temperature. R. mucilaginosa LSL offered the advantage of internal redox cofactor recycling. Notably, the biocatalyst was compatible with all the chemicals required namely sodium azide, copper sulfate and alkynes and showed a broad substrate scope reducing small-bulky and bulky-bulky ketones stereoselectively. Considering this, two one-pot processes were assessed to synthesize enantiopure (R)-β-hydroxytriazoles. A one-pot, three-step sequential transformation allowed obtaining enantiopure products up to 65% yield starting from α-chloro arylketones. On the other hand, with α-bromo arylketones, a one-pot cascade process furnished the same products in ca 80% isolated yield.Fil: Aguirre Pranzoni, Celeste Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de FĂsica Aplicada "Dr. Jorge AndrĂ©s Zgrablich". Universidad Nacional de San Luis. Facultad de Ciencias FĂsico Matemáticas y Naturales. Instituto de FĂsica Aplicada "Dr. Jorge AndrĂ©s Zgrablich"; ArgentinaFil: Tosso, Rodrigo David. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto de Investigaciones en FĂsico-quĂmica de CĂłrdoba. Universidad Nacional de CĂłrdoba. Facultad de Ciencias QuĂmicas. Instituto de Investigaciones en FĂsico-quĂmica de CĂłrdoba; ArgentinaFil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; Argentin
Synthesis, biological evaluation and molecular modeling studies of substitutedN-benzyl-2-phenylethanamines as cholinesterase inhibitors
In this work, we report the synthesis of a series of derivatives of N-benzyl-2-phenylethanamine which is the framework of norbelladine, the natural common precursor of the Amaryllidaceae alkaloids. These compounds were assessed in the inhibition of both AChE and BChE which are the enzymes responsible for the breakdown of acetylcholine and hence they constitute targets in the palliative treatment of Alzheimer's disease. In particular, brominated derivatives exhibited the lowest IC50 values against AChE. Interestingly, the presence of iodine in one of the aromatic rings highly increased the inhibition of BChE compared to its analogues, with an IC50 value similar to that of galantamine, which is the reference compound currently used in the treatment of AD. A possible mechanism of action for these compounds was determined by molecular modeling studies using combined techniques of docking and molecular dynamics simulations.Fil: Carmona Viglianco, Maria Florencia. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Zaragoza Puchol, JosĂ© Daniel. Universidad Nacional de San Juan. Facultad de IngenierĂa. Instituto de BiotecnologĂa; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Juan; ArgentinaFil: Parravicini, Oscar. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones BiolĂłgicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias FĂsico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones BiolĂłgicas de San Luis; ArgentinaFil: Garro, Adriana. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones BiolĂłgicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias FĂsico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones BiolĂłgicas de San Luis; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones BiolĂłgicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias FĂsico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones BiolĂłgicas de San Luis; ArgentinaFil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de IngenierĂa. Instituto de BiotecnologĂa; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Juan; ArgentinaFil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; Argentin
New trends in organic synthesis with oxidative enzymes
Oxidative enzymes constitute privileged catalysts in organic synthesis. Environmentally benign reaction conditions along with high selectivity are the most appealing characteristic shown by these biocatalysts in contrast to classical metal-based reagents. The present review surveys new perspectives and concepts derived from oxidative enzymatic processes, comprising oxidative C-C bond forming
reactions, atroposelective oxidations, oxidative dynamic processes, interconnected reactions, cyclic deracemizations, oxidative desymmetrizations and artificial oxidative enzymes. Selected examples taken from the recent literature are discussed, highlighting relevant aspects from a synthetic point of view. Thus, application of these biocatalyzed reactions in the preparation of chiral high-added value compounds is also outlined. Finally, future perspectives for the development of novel oxidative enzymatic processes and further applications of well settled ones are presented.Fil: de Gonzalo, Gonzalo. Universidad de Oviedo; EspañaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto de Investigaciones en FĂsico-quĂmica de CĂłrdoba. Universidad Nacional de CĂłrdoba. Facultad de Ciencias QuĂmicas. Instituto de Investigaciones en FĂsico-quĂmica de CĂłrdoba; Argentin
Effects of elicitor and copper sulfate on grindelic acid production in submerged cultures of Grindelia pulchella
Grindelia pulchella callus and cell suspension cultures were established from seedling leaves. When several phytoregulator supplementations were assayed in solid Murashige and Skoog medium containing 3% (w/v) of sucrose (MS medium), combinations of indole-3-butyric acid (IBA) and N6-benzylaminopurine (BA) resulted the most appropriate conditions to generate fast growing friable calli with detectable levels of grindelic acid. Moreover, the same basal media supplemented with 20.0 µM IBA/4.4 µM BA was found to be optimal for cell growth in submerged cultures (µmax = 0.26 days-1) while the addition of 20.0 µM IBA/18.0 µM BA resulted in a relative higher metabolite production (4.55 mg/gDW) when the inocula was 5% (v/v). Furthermore, three different stress factors and combinations of them were used to elicit cell suspensions. These experiments demonstrated that the combination of CuSO4 and dimethylsulfoxide (DMSO) increase the grindelic acid production to 2.63 mg/gDW in the elicited essay versus 0.756 mg/gDW in the control, at expense of cell growth. In contrast, the addition of jasmonic acid (JA) alone and combined with DMSO neither affected cell growth nor grindelic acid accumulation.Fil: Hernandez, Xenia Elma. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Giordano, Oscar Santiago. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; Argentin
Deracemization of secondary alcohols by chemo-enzymatic sequence with plant cells
A screening based on undifferentiated plant cells allowed identifying Gardenia jasminoides as the best biocatalyst to perform the kinetic resolution of 1-phenylethanol. This species was further tested for its ability to oxidize stereoselectively the (S)-isomers from racemic mixtures of secondary alcohols leaving their antipodes unaffected in Tris-HCl buffer. Those substrates which afforded the best results in the kinetic resolution were subjected to a chemo-enzymatic sequence of deracemization. G. jasminoides immobilized cells in calcium alginate were used for the oxidation of the (S)-enantiomers and, in a second step, NaBH4 was added to the same vessel for the reduction of the corresponding ketone. The sequential repetition of these two steps allowed obtaining the R-alcohols in 82-90% yield in high optical purity (71-96% ee). Despite the viability of the cells is affected by the chemical reagent, their enzymes remain active due to the protective environment of the calcium alginate beads.Fil: Magallanes Noguera, Cynthia Alejandra. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Ferrari, Monica Marta. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; Argentin
Lyophilized Rhodotorula yeast as all-in-one redox biocatalyst: Access to enantiopure building blocks by simple chemoenzymatic one-pot procedures
Rhodotorula sp. LSL, isolated from a local landfarming was able to catalyze the reduction of prochiral arylketones into sec-alcohols with excellent Prelog stereoselectivity (ee > 99%). The use of resting and lyophilized cells was optimized accessing to an easy-to-use whole cell biocatalyst that efficiently works even under non-sterile conditions, without the addition of external cofactors and using plain water as solvent. The catalyst resistance in alkaline media enabled (chemo)enzymatic one-pot procedures at high pH values. So a simple and efficient methodology was applied to prepare alternatively enantiopure β-halohydrins, terminal diols and epoxides from aromatic α-haloketones.Fil: Aguirre Pranzoni, Celeste Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico San Luis. Instituto de Investigaciones En TecnologĂa QuĂmica; ArgentinaFil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico CĂłrdoba. Instituto de Investigaciones En FĂsicoquĂmica de CĂłrdoba; ArgentinaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico San Luis. Instituto de Investigaciones En TecnologĂa QuĂmica; ArgentinaFil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico San Luis. Instituto de Investigaciones En TecnologĂa QuĂmica; Argentin
Aspergillus genus as a source of new catalysts for sulfide oxidation
This work extends the present knowledge about the ability of filamentous fungi to selectively transform sulfur-containing compounds. Here, it has been demonstrated that several species of the Aspergillus genus are able to perform chemo- and stereoselective oxidation of organic sulfides. Two substrates were chosen as models, the aliphatic cyclohexyl(methyl)sulfide and the alkyl aryl sulfide, thioanisole. All the tested strains showed the ability to oxidize cyclohexyl(methyl)sulfide, whereas most of them oxidized thioanisole. In all cases R-stereoselectivity was observed and full chemoselectivity was verified since no sulfone was detected. Several biotransformation parameters such as the employment of growing or resting cell, different head-space volumes, age of the cultures, bio-reaction times and biocatalyst/substrate ratios resulted crucial in the optimization of the processes. Thus, when using isopropyl alcohol as co-solvent in growing cell systems, chemo- and stereoselectivity could be modulated. Among the studied strains, Aspergillus japonicus ICFC 744/11 was found to be a promising whole cell biocatalyst to prepare enantioenriched sulfoxides since after optimization, either conversion and optical purity of (R)-cyclohexyl(methyl)sulfoxide were excellent (c: 100%, ee > 99%). © 2012 Elsevier B.V.Fil: Mascotti, MarĂa Laura. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; ArgentinaFil: Bisogno, Fabricio Román. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto de Investigaciones en FĂsico-quĂmica de CĂłrdoba. Universidad Nacional de CĂłrdoba. Facultad de Ciencias QuĂmicas. Instituto de Investigaciones en FĂsico-quĂmica de CĂłrdoba; ArgentinaFil: De Gonzalo, Gonzalo. Universidad de Oviedo; EspañaFil: Kurina Sanz, Marcela Beatriz. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - San Luis. Instituto de Investigaciones en TecnologĂa QuĂmica. Universidad Nacional de San Luis. Facultad de QuĂmica, BioquĂmica y Farmacia. Instituto de Investigaciones en TecnologĂa QuĂmica; Argentin