Pyrrolnitrin

Pyrrolnitrin is an antifungal antibiotic.[1] Pseudomonas pyrrocinia and other Pseudomonas species produce pyrrolnitrin from tryptophan as secondary metabolite.[2][3] The fungicides fenpiclonil and fludioxonil are chemically related to pyrrolnitrin.[4][5]

Pyrrolnitrin
Names
Preferred IUPAC name
3-Chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.012.557
EC Number
  • 213-812-7
KEGG
MeSH D011764
PubChem CID
UNII
InChI
  • InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H N
    Key: QJBZDBLBQWFTPZ-UHFFFAOYSA-N N
  • InChI=1/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H
    Key: QJBZDBLBQWFTPZ-UHFFFAOYAG
SMILES
  • C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl
Properties
Chemical formula
 C10H6Cl2N2O2
Molar mass 257.07284
Pharmacology
D01AA07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

References
  1. Gordee, R. S.; Matthews, T. R. (1969). "Systemic antifungal activity of pyrrolnitrin". Applied Microbiology. 17 (5): 690–694. doi:10.1128/AEM.17.5.690-694.1969. PMC 377781. PMID 5785951.
  2. Zhu, X.; Van Pee, K. -H.; Naismith, J. H. (2010). "The Ternary Complex of PrnB (the Second Enzyme in the Pyrrolnitrin Biosynthesis Pathway), Tryptophan, and Cyanide Yields New Mechanistic Insights into the Indolamine Dioxygenase Superfamily". Journal of Biological Chemistry. 285 (27): 21126–21133. doi:10.1074/jbc.M110.120485. PMC 2898318. PMID 20421301.
  3. Park, J. Y.; Oh, S. A.; Anderson, A. J.; Neiswender, J.; Kim, J. -C.; Kim, Y. C. (2011). "Production of the antifungal compounds phenazine and pyrrolnitrin from Pseudomonas chlororaphis O6 is differentially regulated by glucose". Letters in Applied Microbiology. 52 (5): 532–537. doi:10.1111/j.1472-765X.2011.03036.x. PMID 21362001.
  4. Pillonel, Ch; Knauf-beiter, G.; Steinemann, A. (2003). "Fungicides, Phenylpyrroles". Encyclopedia of Agrochemicals. doi:10.1002/047126363X.agr106. ISBN 047126363X.
  5. Jespers, A.B.K.; Davidse, L.C.; Dewaard, M.A. (1993). "Biochemical Effects of the Phenylpyrrole Fungicide Fenpiclonil in Fusarium sulphureum (Schlecht)". Pesticide Biochemistry and Physiology. 45 (2): 116–129. doi:10.1006/pest.1993.1014. ISSN 0048-3575.


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