Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system (Articolo in rivista)

Type

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

Label

• Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system (Articolo in rivista) (literal)

Anno

• 2014-01-01T00:00:00+01:00 (literal)

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

• 10.1039/c3ra47753c (literal)

Alternative label

• R. Bernini, F. Crisante; P. Gentili, S. Menta, F. Morana, M. Pierini (2014)
  Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system
  in RSC advances
  (literal)

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

• R. Bernini, F. Crisante; P. Gentili, S. Menta, F. Morana, M. Pierini (literal)

Pagina inizio

• 8183 (literal)

Pagina fine

• 8190 (literal)

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

• http://www.scopus.com/inward/record.url?eid=2-s2.0-84893184945&partnerID=q2rCbXpz (literal)

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

• 4 (literal)

Rivista

• RSC advances (Rivista)

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

• 8 (literal)

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

• 16 (literal)

Note

• Scopu (literal)

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

• Dipartimento di Scienze e Tecnologie per l'Agricoltura le Foreste, la Natura e l'Energia (DAFNE), Università Degli Studi della Tuscia, Via S. Camillo De Lellis, 01100 Viterbo, Italy; Dipartimento di Chimica, IMC-CNR Sezione Meccanismi di Reazione, Università Degli Studi la Sapienza, P. le A. Moro 5, 00185 Rome, Italy; Dipartimento di Chimica e Tecnologia Del Farmaco, Università Degli Studi la Sapienza, P. le A. Moro 5, I-00185 Rome, Italy (literal)

Titolo

• Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system (literal)

Abstract

• Unreported methylated catechin and epicatechin derivatives 5 and 6 were synthesized by an oxa-Pictet-Spengler reaction. Catechin 5 shows the B and C rings coplanar because of the formation of a trans junction between the C ring and the newly generated six-term cycle D, in turn condensed to ring B. In contrast, epicatechin 6 presents a bent geometry due to the establishment of a cis junction between the C ring and the newly formed cycle D. The oxidation of compounds 5 and 6 in the presence of the Trametes villosa laccase/1- hydroxybenzotriazole (HBT) system was investigated under aerobic conditions in both a biphasic system and a reverse micelle. The unexpected different chemoselective oxidation at the benzylic position of catechin and epicatechin derivatives 5 and 6 has been rationalized using a molecular modelling approach. These results demonstrate that the Trametes villosa laccase/HBT system represents a useful tool to functionalize the C-2 or C-4 position of phenolic compounds depending on the structural features. © 2014 The Royal Society of Chemistry. (literal)

Prodotto di

• Metodologie, nanoparticelle e nutraceutici in nanomedicina (PM.P05.002.001) (Modulo)
• Istituto di metodologie chimiche (IMC) (Istituto)

Autore CNR

• PATRIZIA GENTILI (Persona)

Incoming links:

Prodotto

• Istituto di metodologie chimiche (IMC) (Istituto)
• Metodologie, nanoparticelle e nutraceutici in nanomedicina (PM.P05.002.001) (Modulo)

Autore CNR di

• PATRIZIA GENTILI (Persona)

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

• RSC advances (Rivista)