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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)
Author Süssenbacher Iris, Christ Bastien, Hörtensteiner Stefan, Kräutler Bernhard,
Project Chlorophyll breakdown: catabolite modification and transport, and the relation to stoma function and cell death signalling
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Original article (peer-reviewed)

Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Volume (Issue) 20(1)
Page(s) 87 - 92
Title of proceedings Chemistry (Weinheim an der Bergstrasse, Germany)
DOI 10.1002/chem.201303398

Open Access

URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201303398/abstract
Type of Open Access Publisher (Gold Open Access)

Abstract

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.
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