BGC0002075: pyreudione A biosynthetic gene cluster from Pseudomonas fluorescens
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Location: 27,345 - 31,238 nt. (total: 3,894 nt).
This entry is originally from NCBI GenBank NZ_LVEJ01000014.1.

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core biosynthetic genes
additional biosynthetic genes
transport-related genes
regulatory genes
other genes
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General
Compounds
Genes
Biosynthesis
Operons
History
NRPS/PKS domains
KnownClusterBlast
General information about the BGC
MIBiG accession BGC0002075
Short description pyreudione A biosynthetic gene cluster from Pseudomonas fluorescens
Status Quality: questionable
The quality level of this entry.

Status: active
The status of this entry.

Completeness: complete
Whether the entry covers everything needed for the pathway producing the compound(s)
Remarks "The single NRPS is multispecific with regards to amino acid activation (L-proline, L-pipecolic acid) and C starter domain substrate specificity (3-oxo fatty acids of different length and saturation), thereby allowing to form different tetramic acids via Dieckmann-type cyclization. Depending on the amino acid substrate, acyltetramic acids with a pyrrolizidine (A domain substrate: L-proline) or an indolicidine (A domain substrate: L-pipecolic acid) core structure are formed."
Biosynthetic class(es)
  • NRPS (Type I)
Loci
NZ_LVEJ01000014.1
27345 - 31238
via Knock-out studies, Enzymatic assays, Heterologous expression
Compounds
  • pyreudione A
  • pyreudione B
  • pyreudione C
  • pyreudione D
  • pyreudione E
Species Pseudomonas fluorescens [taxonomy]
References
Chemical products information
pyreudione A Evidence: NMR [1], Mass spectrometry [1], Total synthesis [1]
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C15H23N1O3
Chemical database entries
NPAtlas
ChEBI
PubCHEM
pyreudione B Evidence: NMR [1], Total synthesis [1], Mass spectrometry [1]
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C17H27N1O3
Chemical database entries
ChEBI
NPAtlas
PubCHEM
pyreudione C Evidence: NMR [1], Mass spectrometry [1]
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C17H25N1O3
Chemical database entries
ChEBI
PubCHEM
NPAtlas
pyreudione D Evidence: NMR [1], Mass spectrometry [1]
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C19H29N1O3
Chemical database entries
PubCHEM
NPAtlas
ChEBI
pyreudione E Evidence: NMR [2], Mass spectrometry [2], Total synthesis [2]
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C16H25N1O3
Chemical database entries
PubCHEM
NPAtlas
ChEBI
List of genes involved in compound(s) production
Identifiers Position Product Functions Evidence Extra
  • A8O26_RS14270
  • WP_064118616.1
 27345 - 31238 (+) non-ribosomal peptide synthetase
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    Biosynthesis information

    Biosynthetic paths

    pyreudione A
    Show structure
    Pathway: pys [1], [2]
    Comment: The single NRPS is multispecific with regards to amino acid activation (L-proline, L-pipecolic acid) and C starter domain substrate specificity (3-oxo fatty acids of different length and saturation), thereby allowing to form different tetramic acids via Dieckmann-type cyclization. Depending on the amino acid substrate, acyltetramic acids with a pyrrolizidine (A domain substrate: L-proline) or an indolicidine (A domain substrate: L-pipecolic acid) core structure are formed. Product if saturated C10 fatty acid is condensed to L-proline
    pyreudione B
    Show structure
    Pathway: pys [1], [2]
    Comment: Product if saturated C12 fatty acid is condensed to L-proline
    pyreudione C
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    Pathway: pys [1], [2]
    Comment: Product if unsaturated C12 fatty acid is condensed to L-proline
    pyreudione D
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    Pathway: pys [1], [2]
    Comment: Product if unsaturated C14 fatty acid is condensed to L-proline
    pyreudione E
    Show structure
    Pathway: pys [1], [2]
    Comment: Product if L-pipecolic acid is activated by the A-domain and condensed with saturated C10 fatty acid

    Biosynthetic modules

    Name
    pys
    Type
    nrps-type1
    Genes
    A8O26_RS14270
    Substrates
    proline, pipecolic acid, 4-hydroxyproline, 4-oxoproline, azetidine-2-carboxylic acid (evidence: ATP-PPi exchange assay [2])
    Integrated Monomers
    Domains
    condensation (Starter), adenylation, carrier (PCP)
    Operons
    Genes Evidence
    A8O26_RS14270
    Annotation changelog

    Entry version: next

    Date
    Changes
    Submitters
    Reviewers
    2024-06-04
    MIBiG v4 annotathon
    • (ID: 6CADHILFODRMCII55WHSHZ6V)
    • (ID: MGLE5JJ3S32DQA3YR5WPYH4W)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)

    Entry version: 2

    Date
    Changes
    Submitters
    Reviewers
    2022-10-07
    Update chemical activity to schema version 2.11
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    2022-10-07
    Changed chemical structures for compounds: pyreudione E, pyreudione B, pyreudione D.
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)

    Entry version: 1

    Date
    Changes
    Submitters
    Reviewers
    2022-09-15
    Submitted
    • (ID: 6CADHILFODRMCII55WHSHZ6V)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    2022-09-15
    Corrected NRP module activity
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    2022-09-15
    Removed gene names of 'No gene ID'
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    2022-09-15
    Added version to NCBI accession
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    2022-09-15
    Updated NRP substrate specificities
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    • (ID: AAAAAAAAAAAAAAAAAAAAAAAA)
    Detailed domain annotation
    Shows NRPS- and PKS-related domains for each feature that contains them. Click on each domain for more information about the domain's location, consensus monomer prediction, and other details.
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