Abstract:
The reduction of cyclic and acyclic 1,2-diketones was investigated by employing whole cells of the yeast Rhodotorula minuta as biocatalyst. The reactions showed a variable degree of regio- and enantioselectivity depending on the nature of the substrate. In the case of cyclic diketones, the reduction afforded a mixture of diastereomeric diols only. The reduction of acyclic diketones allowed production of both the hydroxy ketone and the diol, in a two-step reaction. The first step was highly regio- and stereoselective, affording the hydroxy ketone of (S)-configuration with high enantiomeric excess. After longer reaction times the corresponding (S,S)-diols were obtained in high yield and diastereomeric excess. © 2010 Informa UK Ltd.
Registro:
Documento: |
Artículo
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Título: | Rhodotorula minuta-mediated bioreduction of 1,2-diketones |
Autor: | Monsalve, L.N.; Cerrutti, P.; Galvagno, M.A.; Baldessari, A. |
Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina Departamento de Ingeniería Química, Facultad de Ingeniería, Universidad de Buenos Aires, Buenos Aires, Argentina IIB-Intech-CONICET-UNSAM, Buenos Aires, Argentina
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Palabras clave: | 1,2-Diketones; Bioreduction; Rhodotorula minuta; Bioreductions; Diastereomeric; Diastereomeric excess; Diketones; Enantiomeric excess; High yield; Reaction time; Stereo-selective; Two-step reactions; Whole cell; Enantioselectivity; Ketones; 1,2 cyclohexanediol derivative; 1,2 diketone derivative; 2 phenyl 2,3 propanedione; 2,3 butanedione; 2,3 pentanedione; diketone; unclassified drug; article; controlled study; enantiomer; enantioselectivity; gas liquid chromatography; nonhuman; reduction; Rhodotorula; Rhodotorula minuta; stereochemistry; Rhodotorula minuta |
Año: | 2010
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Volumen: | 28
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Número: | 2
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Página de inicio: | 137
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Página de fin: | 143
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DOI: |
http://dx.doi.org/10.3109/10242420903515445 |
Título revista: | Biocatalysis and Biotransformation
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Título revista abreviado: | Biocatal. Biotransform.
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ISSN: | 10242422
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CODEN: | BOBOE
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CAS: | 2,3 butanedione, 431-03-8
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v28_n2_p137_Monsalve |
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Citas:
---------- APA ----------
Monsalve, L.N., Cerrutti, P., Galvagno, M.A. & Baldessari, A.
(2010)
. Rhodotorula minuta-mediated bioreduction of 1,2-diketones. Biocatalysis and Biotransformation, 28(2), 137-143.
http://dx.doi.org/10.3109/10242420903515445---------- CHICAGO ----------
Monsalve, L.N., Cerrutti, P., Galvagno, M.A., Baldessari, A.
"Rhodotorula minuta-mediated bioreduction of 1,2-diketones"
. Biocatalysis and Biotransformation 28, no. 2
(2010) : 137-143.
http://dx.doi.org/10.3109/10242420903515445---------- MLA ----------
Monsalve, L.N., Cerrutti, P., Galvagno, M.A., Baldessari, A.
"Rhodotorula minuta-mediated bioreduction of 1,2-diketones"
. Biocatalysis and Biotransformation, vol. 28, no. 2, 2010, pp. 137-143.
http://dx.doi.org/10.3109/10242420903515445---------- VANCOUVER ----------
Monsalve, L.N., Cerrutti, P., Galvagno, M.A., Baldessari, A. Rhodotorula minuta-mediated bioreduction of 1,2-diketones. Biocatal. Biotransform. 2010;28(2):137-143.
http://dx.doi.org/10.3109/10242420903515445