1994
DOI: 10.1002/ange.19941060321
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Biosynthese von Nitroverbindungen: Die enzymatische Oxidation einer Vorstufe mit Aminogruppe zu Pyrrolnitrin

Abstract: Die enzymatische Reaktion Aryl‐NH2→‐Aryl‐NO2, deren nichtenzymatische Version drastische Bedingungen erfordert, war bisher kaum untersucht. Aus einem Bakterienstamm der Gattung Pseudomonas, der das Antibioticum Pyrrolnitrin 2 produziert, konnte eine Chlorperoxidase (CPO‐P) isoliert werden. Sie katalysiert in vitro nicht nur Halogenierungen, sondern auch die Oxidation der Vorstufe 1 zu 2.

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Cited by 13 publications
(4 citation statements)
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“…Several biosynthetic pathways were proposed. One possibility is the direct nitration of aromatic compounds in the presence of KNO 3 in the medium [22] or by enzymatic oxidation of the amino groups [23]. Nitration can also be the result of peroxynitrite dependent or independent pathways [24,25].…”
Section: Resultsmentioning
confidence: 99%
“…Several biosynthetic pathways were proposed. One possibility is the direct nitration of aromatic compounds in the presence of KNO 3 in the medium [22] or by enzymatic oxidation of the amino groups [23]. Nitration can also be the result of peroxynitrite dependent or independent pathways [24,25].…”
Section: Resultsmentioning
confidence: 99%
“…Die einzigen vorliegenden Studien über enzymatische Nitrogruppenbildung wurden mit Haloperoxidasen durchgeführt. Diese Enzyme sind keine authentischen N‐Oxygenasen und oxidieren Aminogruppen ausschließlich unter sehr spezifischen, nichtnatürlichen Bedingungen, d. h. nur in vitro, mit einem Überschuss von H 2 O 2 und/oder in der Abwesenheit von Halogenidionen, über die Bildung von reaktiven Peroxospezies 17–19. Darüber hinaus sind Haloperoxidasen wie CPO‐P in natürlicher Umgebung nicht an der Biosynthese von Nitroverbindungen beteiligt, wie die Analyse der Pyrrolnitrin‐Biosynthese‐Gene ergab 13.…”
Section: Methodsunclassified
“…The only existing studies on enzymatic nitro group formation have been carried out with haloperoxidases. These are not genuine N‐oxygenases; they catalyze the oxidation of amino groups only under very specific, non‐natural in‐vitro conditions through the formation of reactive peroxo species, with excess H 2 O 2 and/or in the absence of halide ions 17–19. Furthermore, haloperoxidases such as CPO‐P are not naturally involved in the biosynthesis of nitro compounds, as has been revealed by the analysis genes responsible for pyrrolnitrin biosynthesis 13.…”
Section: Methodsmentioning
confidence: 99%