Zn-complex of a natural yellow chlorophyll catabolite

Abstract

“Non-fluorescent” chlorophyll catabolites (NCCs) were named “rusty pigments” originally, as they easily oxidized to yellow chlorophyll catabolites (YCCs) and other colored natural “phyllobilins.” In the present work, binding of Zn(II)-ions by YCC and its methyl ester YCC-Me, and structural investigations of the resulting Zn(II)-complexes are reported. Binding of Zn-ions to the weakly luminescent YCC or YCC-Me in DMSO produces orange-yellow complexes that exhibit strong green emission. The Zn-complex of YCC-Me was isolated and characterized by UV-vis-, fluorescence-, mass- and NMR-spectra. The data revealed a 2:1 complex, Zn(YCC-Me)[Formula: see text], in which YCC-Me serves as bidentate ligand. The Zn(II)-center in Zn(YCC-Me)[Formula: see text] is, thereby, deduced to be coordinated in a pseudo tetrahedral fashion. Formation of Zn(YCC-Me)[Formula: see text] (and of Zn(YCC)[Formula: see text] is compatible with an isomerization of the lactam form of ring D to the corresponding lactim tautomer in these neutral Zn(II)-complexes.