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dc.contributor.author
Decarlini, Maria Florencia
dc.contributor.author
Aimar, Mario Leandro
dc.contributor.author
Vázquez, Ana M.
dc.contributor.author
Vero, Silvana
dc.contributor.author
Rossi, Laura Isabel
dc.contributor.author
Yang, Pablo
dc.date.available
2018-11-15T15:33:20Z
dc.date.issued
2017-10
dc.identifier.citation
Decarlini, Maria Florencia; Aimar, Mario Leandro; Vázquez, Ana M.; Vero, Silvana; Rossi, Laura Isabel; et al.; Fungi isolated from food samples for an efficient stereoselective production of phenylethanols; Elsevier; Biocatalysis and Agricultural Biotechnology; 12; 10-2017; 275-285
dc.identifier.issn
1878-8181
dc.identifier.uri
http://hdl.handle.net/11336/64535
dc.description.abstract
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.%.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Acetophenones
dc.subject
Biocatalysis
dc.subject
Galactomyces Candidus
dc.subject
Phenylethanols
dc.subject
Rivastigmine
dc.subject
Stereoselective Bioreduction
dc.subject.classification
Otras Ciencias Químicas
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
Fungi isolated from food samples for an efficient stereoselective production of phenylethanols
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-10-22T18:38:47Z
dc.journal.volume
12
dc.journal.pagination
275-285
dc.journal.pais
Países Bajos
dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Decarlini, Maria Florencia. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina
dc.description.fil
Fil: Aimar, Mario Leandro. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; Argentina
dc.description.fil
Fil: Vázquez, Ana M.. Universidad Católica de Córdoba. Facultad de Ciencias Químicas; Argentina
dc.description.fil
Fil: Vero, Silvana. Universidad de la República; Uruguay
dc.description.fil
Fil: 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; Argentina
dc.description.fil
Fil: 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; Argentina
dc.journal.title
Biocatalysis and Agricultural Biotechnology
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1016/j.bcab.2017.10.014
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1878818117304474
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