Flavin-cyclodextrin conjugates: effect of the structure on the catalytic activity in enantioselective sulfoxidations

0388435 - ÚOCHB 2013 RIV GB eng J - Článek v odborném periodiku
Hartman, T. - Herzig, Vladimír - Buděšínský, Miloš - Jindřich, J. - Cibulka, R. - Kraus, Tomáš
Flavin-cyclodextrin conjugates: effect of the structure on the catalytic activity in enantioselective sulfoxidations.
Tetrahedron Asymmetry. Roč. 23, 22/23 (2012), s. 1571-1583. ISSN 0957-4166
Grant CEP: GA ČR GA203/09/1919
Grant ostatní: GA ČR(CZ) GAP207/12/0447
Institucionální podpora: RVO:61388963
Klíčová slova: enzyme mimics * aqueous hydrogen-peroxide * asymmetric sulfide oxidation * kinetic resolution * molecular-oxygen
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.115, rok: 2012

A series of flavin cyclodextrin conjugates has been prepared and tested in the enantioselective oxidations of prochiral aromatic and aliphatic sulfides with hydrogen peroxide. The newly prepared conjugates contain isoalloxazinium or alloxazinium moieties attached to the primary rim of alpha- and beta-cyclodextrins at the C-6 positions. In addition, flavinium units were attached to the secondary rim of the beta-cyclodextrin macrocycle. The relationship between the structural features and the catalytic performance of the conjugates, including those recently reported by us, was analyzed. The rate and enantioselectivity of the sulfoxidations catalyzed by flavin cyclodextrin conjugates are influenced mainly by the size of the cyclodextrin cavity, the type of flavin unit (alloxazine or isoalloxazine), and by the relative orientation of the flavin and cyclodextrin moieties.
Trvalý link: http://hdl.handle.net/11104/0217353