Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system
wnacki, I; Kubicki, M; Szubert, K; Marciniec, B; Bernini, R; Crisante, F; Gentili, P; Menta, S; Morana, F; Pierini, JM
| HERO ID | 4854456 |
|---|---|
| In Press | No |
| Year | 2014 |
| Title | Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system |
| Authors | wnacki, I; Kubicki, M; Szubert, K; Marciniec, B; Bernini, R; Crisante, F; Gentili, P; Menta, S; Morana, F; Pierini, JM |
| Journal | RSC Advances |
| Volume | 4 |
| Issue | 16 |
| Page Numbers | 8183-8190 |
| 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. |
| Doi | 10.1039/c3ra47753c |
| Wosid | WOS:000330799900039 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |