The oxygen-independent coproporphyrinogen III oxidase HemN utilizes harderoporphyrinogen as a reaction intermediate during conversion of coproporphyrinogen III to protoporphyrinogen IX

verfasst von: Katrin Rand, Claudia Noll, Hans Martin Schiebel, Dorit Kemken, Thomas Dülcks, Markus Kalesse, Dirk W. Heinz, Gunhild Layer
Abstract: During heme biosynthesis the oxygen-independent coproporphyrinogen III oxidase HemN catalyzes the oxidative decarboxylation of the two propionate side chains on rings A and B of coproporphyrinogen III to the corresponding vinyl groups to yield protoporphyrinogen IX. Here, the sequence of the two decarboxylation steps during HemN catalysis was investigated. A reaction intermediate of HemN activity was isolated by HPLC analysis and identified as monovinyltripropionic acid porphyrin by mass spectrometry. This monovinylic reaction intermediate exhibited identical chromatographic behavior during HPLC analysis as harderoporphyrin (3-vinyl-8,13,17-tripropionic acid-2,7,12,18- tetramethylporphyrin). Furthermore, HemN was able to utilize chemically synthesized harderoporphyrinogen as substrate and converted it to protoporphyrinogen IX. These results suggest that during HemN catalysis the propionate side chain of ring A of coproporphyrinogen III is decarboxylated prior to that of ring B.
Organisationseinheit(en): Institut für Organische Chemie
Externe Organisation(en): Helmholtz-Zentrum für Infektionsforschung GmbH (HZI)
Technische Universität Braunschweig
Universität Bremen
Typ: Artikel
Journal: Biological chemistry
Band: 391
Seiten: 55-63
Anzahl der Seiten: 9
ISSN: 1431-6730
Publikationsdatum: 01.01.2010
Publikationsstatus: Veröffentlicht
Peer-reviewed: Ja
ASJC Scopus Sachgebiete: Biochemie, Molekularbiologie, Klinische Biochemie
Elektronische Version(en): https://doi.org/10.1515/BC.2010.006 (Zugang: Unbekannt)

BibTeX

@article{ec865f217959424da42f3903e6d54403,
title = "The oxygen-independent coproporphyrinogen III oxidase HemN utilizes harderoporphyrinogen as a reaction intermediate during conversion of coproporphyrinogen III to protoporphyrinogen IX",
abstract = "During heme biosynthesis the oxygen-independent coproporphyrinogen III oxidase HemN catalyzes the oxidative decarboxylation of the two propionate side chains on rings A and B of coproporphyrinogen III to the corresponding vinyl groups to yield protoporphyrinogen IX. Here, the sequence of the two decarboxylation steps during HemN catalysis was investigated. A reaction intermediate of HemN activity was isolated by HPLC analysis and identified as monovinyltripropionic acid porphyrin by mass spectrometry. This monovinylic reaction intermediate exhibited identical chromatographic behavior during HPLC analysis as harderoporphyrin (3-vinyl-8,13,17-tripropionic acid-2,7,12,18- tetramethylporphyrin). Furthermore, HemN was able to utilize chemically synthesized harderoporphyrinogen as substrate and converted it to protoporphyrinogen IX. These results suggest that during HemN catalysis the propionate side chain of ring A of coproporphyrinogen III is decarboxylated prior to that of ring B.",
keywords = "Escherichia coli, Heme biosynthesis, Oxidative decarboxylation",
author = "Katrin Rand and Claudia Noll and Schiebel, {Hans Martin} and Dorit Kemken and Thomas D{\"u}lcks and Markus Kalesse and Heinz, {Dirk W.} and Gunhild Layer",
note = "Funding Information: We thank Prof. Jean-Charles Deybach and Caroline Schmitt (University of Paris VII, France) for the gift of plasmids pGEX-2T:CPO and pGEX-2T:CPO(R401K). We would like to thank Prof. Dieter Jahn for continuous support and helpful discussions. This work was supported by grants from the Deutsche Forschungsgemeinschaft to D.W.H. and by the Emmy-Noether-Program of the Deutsche For-schungsgemeinschaft to G.L. Funds from the Fonds der Chemischen Industrie are gratefully acknowledged by G.L. and D.W.H.",
year = "2010",
month = jan,
day = "1",
doi = "10.1515/BC.2010.006",
language = "English",
volume = "391",
pages = "55--63",
journal = "Biological chemistry",
issn = "1431-6730",
publisher = "Walter de Gruyter GmbH",
number = "1",
}