Steric Effects on the Stereochemistry of Old Yellow Enzyme-Mediated Reductions of Unsaturated Diesters: Flipping of the Substrate within the Enzyme Active Site Induced by Structural Modifications (Articolo in rivista)

Type

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

Label

• Steric Effects on the Stereochemistry of Old Yellow Enzyme-Mediated Reductions of Unsaturated Diesters: Flipping of the Substrate within the Enzyme Active Site Induced by Structural Modifications (Articolo in rivista) (literal)

Anno

• 2012-01-01T00:00:00+01:00 (literal)

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

• 10.1002/adsc.201200471 (literal)

Alternative label

• Brenna, Elisabetta; Gatti, Francesco G.; Manfredi, Alessia; Monti, Daniela; Parmeggiani, Fabio (2012)
  Steric Effects on the Stereochemistry of Old Yellow Enzyme-Mediated Reductions of Unsaturated Diesters: Flipping of the Substrate within the Enzyme Active Site Induced by Structural Modifications
  in Advanced synthesis & catalysis (Print)
  (literal)

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

• Brenna, Elisabetta; Gatti, Francesco G.; Manfredi, Alessia; Monti, Daniela; Parmeggiani, Fabio (literal)

Pagina inizio

• 2859 (literal)

Pagina fine

• 2864 (literal)

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

• 354 (literal)

Rivista

• Advanced synthesis & catalysis (Rivista)

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

• 6 (literal)

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

• 14-15 (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

• Steric Effects on the Stereochemistry of Old Yellow Enzyme-Mediated Reductions of Unsaturated Diesters: Flipping of the Substrate within the Enzyme Active Site Induced by Structural Modifications (literal)

Abstract

• The ene-reductase-mediated reduction of the carbon-carbon double bond of some alkyl 2-substituted butenedioates was investigated. The stereochemical outcome of the reaction was found to be influenced by steric effects. Ethyl and butyl citraconates were converted into the corresponding alkyl (R)-2-methylsuccinates with excellent enantioselectivity, whereas ethyl and butyl mesaconates were completely unreactive. Methyl 2-substituted fumarates were reduced to enantiomerically enriched methyl (S)-2-substituted succinates, whereas the (Z)-stereoisomers were left unreacted by ene-reductases. Labelling experiments were performed to investigate the mechanism of these bioreductions and explain their stereochemical outcome. (literal)

Prodotto di

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

Autore CNR

• DANIELA MONTI (Unità di personale interno)
• MARIA ELISABETTA BRENNA (Unità di personale esterno)

Insieme di parole chiave

• Keywords of "Steric Effects on the Stereochemistry of Old Yellow Enzyme-Mediated Reductions of Unsaturated Diesters: Flipping of the Substrate within the Enzyme Active Site Induced by Structural Modifications" (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

• DANIELA MONTI (Unità di personale interno)
• MARIA ELISABETTA BRENNA (Unità di personale esterno)

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

• Advanced synthesis & catalysis (Rivista)

Insieme di parole chiave di

• Keywords of "Steric Effects on the Stereochemistry of Old Yellow Enzyme-Mediated Reductions of Unsaturated Diesters: Flipping of the Substrate within the Enzyme Active Site Induced by Structural Modifications" (Insieme di parole chiave)