Diastero- and enantioselective bioreduction of ethyl 2-(4-chlophenoxy)-3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts (Articolo in rivista)

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

Label

• Diastero- and enantioselective bioreduction of ethyl 2-(4-chlophenoxy)-3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts (Articolo in rivista) (literal)

Anno

• 2004-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1016/j.tetasy.2004.08.028 (literal)

Alternative label

• Perrone M.G. 1, Santandrea E. 1, Scilimati A. 1, Syldatk C. 2 , Tortorella V. 1, Capitelli F. 3, Bertolasi V. 4 (2004)
  Diastero- and enantioselective bioreduction of ethyl 2-(4-chlophenoxy)-3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts
  in Tetrahedron: asymmetry (Print)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Perrone M.G. 1, Santandrea E. 1, Scilimati A. 1, Syldatk C. 2 , Tortorella V. 1, Capitelli F. 3, Bertolasi V. 4 (literal)

Pagina inizio

• 3511 (literal)

Pagina fine

• 3517 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 15 (literal)

Rivista

• Tetrahedron: asymmetry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

• 6 (literal)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• 1- Dip. Farmaco-Chimico, Univ. di Bari 2- Univ. Karlsruhe, Germany 3- CNR-IC, Sede di Bari 4- Dip. di Chimica e Centro di Strutturistica Diffrattometrica, Ferrara (literal)

Titolo

• Diastero- and enantioselective bioreduction of ethyl 2-(4-chlophenoxy)-3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts (literal)

Abstract

• Growing and resting cells of several yeasts, which catalyze the hydride transfer to a carbonyl, were screened and used in conditions to find out the suitable methodology to prepare clofibrate analogues. Clofibrate is an antilipidemic drug. In particular, the bioreduction of ethyl 2-(4-chlorophenoxy)-3-oxobutanoate 1 was investigated to separately prepare the four possible stereoisomers of the ethyl 2-(4-chlorophenoxy)-3-hydroxybutanoate 2. Compound (2R,3S)-2 was prepared with ee = 97% and 73% yield in the presence of Kluyveromyces marxianus; (2S,3S)-2 preparation with ee > 99% in 9% and 33% yield was mediated by Saccharomyces cerevisiae CBS 7336 and Trigonopsis variabilis, respectively. Diastereomeric excess values of all the reactions investigated were up to > 99%. Furthermore, enantiomeric excesses of the bioconversions varied between 2% and > 99% using growing cells and, 12% and > 99% using resting cells. The absolute configuration of (2R,3S)-2 was established by X-ray analysis of the corresponding acid 3. (literal)

Prodotto di

• Institute of Crystallography (IC) (Istituto)
• Sviluppo e Applicazioni di Metodi Cristallografici (PM.P06.002.001) (Modulo)

Autore CNR

• FRANCESCO CAPITELLI (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "Diastero- and enantioselective bioreduction of ethyl 2-(4-chlophenoxy)-3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts" (Insieme di parole chiave)

Incoming links:

Prodotto

• Institute of Crystallography (IC) (Istituto)
• Sviluppo e Applicazioni di Metodi Cristallografici (PM.P06.002.001) (Modulo)

Autore CNR di

• FRANCESCO CAPITELLI (Unità di personale interno)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Tetrahedron: asymmetry (Rivista)

Insieme di parole chiave di

• Parole chiave di "Diastero- and enantioselective bioreduction of ethyl 2-(4-chlophenoxy)-3-oxobutanoate clofibrate analogues by Kluyveromyces marxianus and other whole cell biocatalysts" (Insieme di parole chiave)