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.

Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system / R., Bernini; Crisante, Fernanda; Gentili, Patrizia; Menta, Sergio; F., Morana; Pierini, Marco. - In: RSC ADVANCES. - ISSN 2046-2069. - 4:(2014), pp. 8183-8190. [10.1039/c3ra47753c]

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

CRISANTE, Fernanda
Membro del Collaboration Group
;
GENTILI, Patrizia
Conceptualization
;
MENTA, SERGIO
Membro del Collaboration Group
;
PIERINI, MARCO
Membro del Collaboration Group
2014

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
Laccase; 1-hydroxybenzotriazole; catechin; epicatechin; oxidation
01 Pubblicazione su rivista::01a Articolo in rivista
Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system / R., Bernini; Crisante, Fernanda; Gentili, Patrizia; Menta, Sergio; F., Morana; Pierini, Marco. - In: RSC ADVANCES. - ISSN 2046-2069. - 4:(2014), pp. 8183-8190. [10.1039/c3ra47753c]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/538991
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