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Hydroxymethylated Dioxobilins in Senescent Arabidopsis thaliana Leaves: Sign of a Puzzling Biosynthetic Intermezzo of Chlorophyll Breakdown.

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Süssenbacher Iris, Kreutz Christoph R, 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) 21(33)
Page(s) 11664 - 70
Title of proceedings Chemistry (Weinheim an der Bergstrasse, Germany)
DOI 10.1002/chem.201501489

Abstract

1-Formyl-19-oxobilin-type tetrapyrroles are characteristic, abundant products of chlorophyll breakdown in senescent leaves. However, in some leaves, 1,19-dioxobilin-type chlorophyll catabolites (DCCs) lacking the formyl group accumulate instead. A P450 enzyme was identified in in vitro studies that removed the formyl group of a primary fluorescent chlorophyll catabolite (pFCC) and generated fluorescent DCCs. These DCCs are precursors of isomeric nonfluorescent DCCs (NDCCs). Here, we report a structural investigation of the NDCCs in senescent leaves of wild-type Arabidopsis thaliana. Four new NDCCs were characterized, two of which carried a stereoselectively added hydroxymethyl group. Such formal DCC hydroxymethylations were previously found in DCCs in leaves of a mutant of A. thaliana. They are now indicated to be a feature of chlorophyll breakdown in A. thaliana, associated with the specific in vivo deformylation of pFCC en route to NDCCs.
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