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Hydroxymethylated phyllobilins: a puzzling new feature of the dioxobilin branch of chlorophyll breakdown.

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2014
Author Süssenbacher Iris, Christ Bastien, Hörtensteiner Stefan, Kräutler Bernhard,
Project Chlorophyll breakdown: analysis of fruit ripening, evolution and regulation
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Original article (peer-reviewed)

Journal Chemistry Eur. J.
Volume (Issue) 20(1)
Page(s) 87 - 92
Title of proceedings Chemistry Eur. J.
DOI 10.1002/chem.201303398


Colorless nonfluorescent chlorophyll (Chl) catabolites (NCCs) are formyloxobilin-type phyllobilins, which are considered the typical products of Chl breakdown in senescent leaves. However, in degreened leaves of some plants, dioxobilin-type Chl catabolites (DCCs) predominate, which lack the formyl group of the NCCs, and which arise from Chl catabolites by oxidative removal of the formyl group by a P450 enzyme. Here a structural investigation of the DCCs in the methylesterase16 mutant of Arabidopsis thaliana is reported. Eight new DCCs were identified and characterized structurally. Strikingly, three of these DCCs carry stereospecifically added hydroxymethyl groups, and represent bilin-type linear tetrapyrroles with an unprecedented modification. Indeed, DCCs show a remarkable structural parallel, otherwise, to the bilins from heme breakdown.