Direct biochemical nitration in the biosynthesis of dioxapyrrolomycin. A unique mechanism for the introduction of nitro groups in microbial products

Carter, Guy T.; Nietsche, Jeanne A.; Goodman, Joseph J.; Torrey, M. J.; Dunne, T. S.; Siegel, Marshall M.; Borders, Donald B.

doi:10.1039/c39890001271

Cited by 32 publications

(25 citation statements)

References 3 publications

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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%

New Aromatic Nitro Compounds from Salegentibacter sp. T436, an Arctic Sea Ice Bacterium: Taxonomy, Fermentation, Isolation and Biological Activities

et al. 2007

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Nineteen aromatic nitro compounds were isolated from the culture broth of an Artic sea ice bacterium. Four of these compounds are new and six compounds are reported from a natural source for the first time. The new natural products showed weak antimicrobial and cytotoxic activities. 2-Nitro-4-(2Ј-nitroethenyl)-phenol was the most potent antimicrobial and cytotoxic substance. Some of the compounds exhibit plant growth modulating activities. Based on its biochemical properties and the 16S rRNA gene sequence, the producing strain can be described as a distinct species within the genus Salegentibacter.

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Section: Resultsmentioning

confidence: 99%

New Aromatic Nitro Compounds from Salegentibacter sp. T436, an Arctic Sea Ice Bacterium: Taxonomy, Fermentation, Isolation and Biological Activities

et al. 2007

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“…The source of the nitro functionality seems to be the inorganic nitrate present in the cultivation medium, as it has been previously described for Streptomyces fumanus, producing dioxapyrrolomycin (4). Recent studies of the biotransformation of tocopherols by Streptomyces catenulae revealed that the nitro derivatives, which were isolated from the culture medium, were formed by a combination of enzymatic nitrate reduction to nitrite followed by a nonenzymatic nitration (15).…”

Section: Discussionmentioning

confidence: 99%

Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona

Zikmundová

Drandarov

Bigler

et al. 2002

Appl Environ Microbiol

136

116

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The biotransformation of the phytoanticipins 2-benzoxazolinone (BOA) and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) by four endophytic fungi isolated from Aphelandra tetragona was studied. Using high-performance liquid chromatography-mass spectrometry, several new products of acylation, oxidation, reduction, hydrolysis, and nitration were identified. Fusarium sambucinum detoxified BOA and HBOA to N-(2-hydroxyphenyl)malonamic acid. Plectosporium tabacinum, Gliocladium cibotii, and Chaetosphaeria sp. transformed HBOA to 2-hydroxy-N-(2-hydroxyphenyl)acetamide, N-(2-hydroxyphenyl)acetamide, N-(2-hydroxy-5-nitrophenyl)acetamide, N-(2-hydroxy-3-nitrophenyl)acetamide, 2-amino-3H-phenoxazin-3-one, 2-acetylamino-3H-phenoxazin-3-one, and 2-(N-hydroxy)acetylamino-3H-phenoxazin-3-one. BOA was not degraded by these three fungal isolates. Using 2-hydroxy-N-(2-hydroxyphenyl)[ 13 C 2 ]acetamide, it was shown that the metabolic pathway for HBOA and BOA degradation leads to o-aminophenol as a key intermediate.

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“…Biosynthetic nitration reactions are rare and usually involve the oxidation of an amine [33]. The chemical mechanism of a NOS-mediated nitration may be complex because NO is unlikely to react directly with indole.…”

Section: Biosynthetic Nitrationmentioning

confidence: 99%

The enzymology of nitric oxide in bacterial pathogenesis and resistance

Crane

2008

Biochemical Society Transactions

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Mammalian NOSs (nitric oxide synthases) are haem-based monoxygenases that oxidize the amino acid arginine to the intracellular signal and protective cytotoxin nitric oxide (NO). Certain strains of mostly Gram-positive bacteria contain homologues of the mammalian NOS catalytic domain that can act as NOSs when suitable reductants are supplied. Crystallographic analyses of bacterial NOSs, with substrates and haem-ligands, have disclosed important features of assembly and active-centre chemistry, both general to the NOS family and specific to the bacterial proteins. The slow reaction profiles and especially stable haem-oxygen species of NOSs derived from bacterial thermophiles have facilitated the study of NOS reaction intermediates. Functionally, bacterial NOSs are distinct from their mammalian counterparts. In certain strains of Streptomyces, they participate in the biosynthetic nitration of plant toxins. In the radiation-resistant bacterium Deinococcus radiodurans, NOSs are also likely to be involved in biosynthetic nitration reactions, but, furthermore, appear to play an important role in the recovery from damage induced by UV radiation.

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Direct biochemical nitration in the biosynthesis of dioxapyrrolomycin. A unique mechanism for the introduction of nitro groups in microbial products

Cited by 32 publications

References 3 publications

New Aromatic Nitro Compounds from Salegentibacter sp. T436, an Arctic Sea Ice Bacterium: Taxonomy, Fermentation, Isolation and Biological Activities

New Aromatic Nitro Compounds from Salegentibacter sp. T436, an Arctic Sea Ice Bacterium: Taxonomy, Fermentation, Isolation and Biological Activities

Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona

The enzymology of nitric oxide in bacterial pathogenesis and resistance

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