ArticleJournal of bacteriology2002
Involvement of a cytochrome P450 monooxygenase in thaxtomin A biosynthesis by Streptomyces acidiscabies.
Article in Journal of bacteriology, 2002. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 46 papers.
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Who cites it
46 citing papers in PubMed, 124 citations in OpenAlex.
- Chromosome-level genome assembly and annotation of a novel potato common scab pathogen.Frontiers in plant science · 2026Article
- Comparative genomics of the niche-specific plant pathogenApplied and environmental microbiology · 2023Article
- Deciphering host-pathogen interaction during Streptomyces spp. infestation of potato.Archives of microbiology · 2023Review
- Genome mining for unknown-unknown natural products.Nature chemical biology · 2023Article
- Natural and engineered cyclodipeptides: Biosynthesis, chemical diversity, and engineering strategies for diversification and high-yield bioproduction.Engineering microbiology · 2023Review
- Transcriptome Analysis of Tryptophan-Induced Resistance against Potato Common Scab.International journal of molecular sciences · 2022Article
- Multiplexed Promoter Engineering for Improving Thaxtomin A Production in HeterologousLife (Basel, Switzerland) · 2022Article
- Nigericin and Geldanamycin Are Phytotoxic Specialized Metabolites Produced by the Plant PathogenMicrobiology spectrum · 2022Article
- Article
- iTRAQ-Based Proteomics Analysis of Response toInternational journal of molecular sciences · 2021Article
- Identification of Novel Rotihibin Analogues inMicrobiology spectrum · 2021Article
- The Ferric-Superoxo Intermediate of the TxtE Nitration Pathway Resists Reduction, Facilitating Its Reaction with Nitric Oxide.Biochemistry · 2021Article
- More P450s Are Involved in Secondary Metabolite Biosynthesis inInternational journal of molecular sciences · 2020Article
- Functional Cross-Talk of MbtH-Like Proteins During Thaxtomin Biosynthesis in the Potato Common Scab PathogenFrontiers in microbiology · 2020Article
- Composition and function of rhizosphere microbiome ofChinese medicine · 2020Article
- TxtH is a key component of the thaxtomin biosynthetic machinery in the potato common scab pathogen Streptomyces scabies.Molecular plant pathology · 2019Article
- A Promiscuous Cytochrome P450 Hydroxylates Aliphatic and Aromatic C-H Bonds of Aromatic 2,5-Diketopiperazines.Chembiochem : a European journal of chemical biology · 2019Article
- The occurrence of potato common scab correlates with the community composition and function of the geocaulosphere soil microbiome.Microbiome · 2019Article
- A Potential Biocontrol AgentFrontiers in microbiology · 2019Article
- Genetic background affects pathogenicity island function and pathogen emergence in Streptomyces.Molecular plant pathology · 2018Article
Corrections and comments
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Authors and funding
5 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The biosynthesis of the thaxtomin cyclic dipeptide phytotoxins proceeds nonribosomally via the thiotemplate mechanism. Acyladenylation, thioesterification, N-methylation, and cyclization of two amino acid substrates are catalyzed by the txtAB-encoded thaxtomin synthetase. Nucleotide sequence analysis of the region 3' of txtAB in Streptomyces acidiscabies 84.104 identified an open reading frame (ORF) encoding a homolog of the P450 monooxygenase gene family. It was proposed that thaxtomin A phenylalanyl hydroxylation was catalyzed by the monooxygenase homolog. The ORF was mutated in S. acidiscabies 84.104 by using an integrative gene disruption construct, and culture filtrate extracts of the mutant were assayed for the presence of dehydroxy derivatives of thaxtomin A. Reversed-phase high-performance liquid chromatography (HPLC) and HPLC-mass spectrometry indicated that the major component in culture filtrate extracts of the mutant was less polar and smaller than thaxtomin A. Comparisons of electrospray mass spectra as well as (1)H- and (13)C-nuclear magnetic resonance spectra of the purified compound with those previously reported for thaxtomins confirmed the structure of the compound as 12,15-N-dimethylcyclo-(L-4-nitrotryptophyl-L-phenylalanyl), the didehydroxy analog of thaxtomin A. The ORF, designated txtC, was cloned and the recombinant six-His-tagged fusion protein produced in Escherichia coli and purified from cell extracts. TxtC produced in E. coli exhibited spectral properties similar to those of cytochrome P450-type hemoproteins that have undergone conversion to the catalytically inactive P420 form. Based on these properties and the high similarity of TxtC to other well-characterized P450 enzymes, we conclude that txtC encodes a cytochrome P450-type monooxygenase required for postcyclization hydroxylation of the cyclic dipeptide.
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