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Artículo

Selection of microbial biocatalysts for the reduction of cyclic and heterocyclic ketones

Bianchi, PaolaIcon ; Fernández Varela, Romina NoeliaIcon ; Bianchi, Dario AlejandroIcon ; Kemppainen, Minna JohannaIcon ; Iribarren, Adolfo MarceloIcon ; Lewkowicz, Elizabeth SandraIcon
Fecha de publicación: 07/2017
Editorial: Elsevier
Revista: Process Biochemistry
ISSN: 1359-5113
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Bioprocesamiento Tecnológico, Biocatálisis, Fermentación

Resumen

The reduction of carbonyl compounds plays an important role in the synthesis of complex chiral molecules. In particular, enantiopure substituted cyclic and heterocyclic compounds are useful intermediates for the synthesis of several antiviral, antitumor, and antibiotic agents, and recently, they have also been used as organocatalysts for C-C addition. Alcohol dehydrogenases (ADH) are enzymes involved in the transformation of prochiral ketones to chiral hydroxyl compounds. While significant scientific effort has been paid to the use of aliphatic and exocyclic ketones as ADH substrates, reports on (hetero)cyclic carbonyl compounds as substrates of these enzymes are scarce. In the present study, 109 bacteria and 36 fungi were screened, resulting in 10 organisms belonging to both kingdoms capable of transforming cyclic and heterocyclic ketones into the corresponding alcohols. Among them, Erwinia chrysanthemi could quantitatively reduce cyclododecanone and Geotrichum candidum could stereoselectively reduce N-Boc-3-piperidone and N-Boc-3-pyrrolidinone to their corresponding (S)-alcohols; however, the anti-Prelog isomer was obtained when acetophenone was the substrate.
Palabras clave: Alcohol Dehydrogenases , (Hetero)Cyclic Ketones , Microbial Reduction , Hierarchical Screening
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info:eu-repo/semantics/embargoedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Atribución-NoComercial-SinDerivadas 2.5 Argentina (CC BY-NC-ND 2.5 AR)
Identificadores
URI: http://hdl.handle.net/11336/22356
URL: http://www.sciencedirect.com/science/article/pii/S1359511317300582
DOI: http://dx.doi.org/10.1016/j.procbio.2017.04.039
Colecciones
Articulos(INGEBI)
Articulos de INST.DE INVEST.EN ING.GENETICA Y BIOL.MOLECULAR "DR. HECTOR N TORRES"
Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Articulos(SEDE CENTRAL)
Articulos de SEDE CENTRAL
Citación
Bianchi, Paola; Fernández Varela, Romina Noelia; Bianchi, Dario Alejandro; Kemppainen, Minna Johanna; Iribarren, Adolfo Marcelo; et al.; Selection of microbial biocatalysts for the reduction of cyclic and heterocyclic ketones; Elsevier; Process Biochemistry; 58; 7-2017; 137-144
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