On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering (Articolo in rivista)

Type

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

Label

• On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering (Articolo in rivista) (literal)

Anno

• 2012-01-01T00:00:00+01:00 (literal)

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

• 10.1016/j.molcatb.2012.02.003 (literal)

Alternative label

• Brenna, Elisabetta; Fronza, Giovanni; Fuganti, Claudio; Gatti, Francesco G.; Manfredi, Alessia; Parmeggiani, Fabio; Ronchi, Paolo (2012)
  On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering
  in Journal of molecular catalysis. B, Enzymatic (Print)
  (literal)

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

• Brenna, Elisabetta; Fronza, Giovanni; Fuganti, Claudio; Gatti, Francesco G.; Manfredi, Alessia; Parmeggiani, Fabio; Ronchi, Paolo (literal)

Pagina inizio

• 94 (literal)

Pagina fine

• 101 (literal)

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

• 84 (literal)

Rivista

• Journal of molecular catalysis. B, Enzymatic (Rivista)

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

• 8 (literal)

Note

• ISI Web of Science (WoS) (literal)

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

• Polytechnic University of Milan; Consiglio Nazionale delle Ricerche (CNR) (literal)

Titolo

• On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering (literal)

Abstract

• The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes. as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction. (C) 2012 Elsevier B.V. All rights reserved. (literal)

Prodotto di

• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)
• Applicazioni sintetiche della biocatalisi (PM.P03.009.002) (Modulo)

Autore CNR

• CLAUDIO FUGANTI (Persona)
• MARIA ELISABETTA BRENNA (Unità di personale esterno)
• GIOVANNI FRONZA (Unità di personale esterno)

Insieme di parole chiave

• Keywords of "On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering" (Insieme di parole chiave)

Incoming links:

Prodotto

• Istituto di chimica del riconoscimento molecolare (ICRM) (Istituto)
• Applicazioni sintetiche della biocatalisi (PM.P03.009.002) (Modulo)

Autore CNR di

• MARIA ELISABETTA BRENNA (Unità di personale esterno)
• CLAUDIO FUGANTI (Persona)
• GIOVANNI FRONZA (Unità di personale esterno)

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

• Journal of molecular catalysis. B, Enzymatic (Rivista)

Insieme di parole chiave di

• Keywords of "On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering" (Insieme di parole chiave)