Pyrrolnitrin

Pyrrolnitrin
Names
	IUPAC name 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
Identifiers
CAS Number	1018-71-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32079 ;
ChemSpider	13314 ;
ECHA InfoCard	100.012.557
EC Number	213-812-7;
KEGG	D01094 ;
MeSH	D011764
PubChem CID	13916;
UNII	N0P24B6EDQ ;
CompTox Dashboard (EPA)	DTXSID9046867 ;
	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 Key: QJBZDBLBQWFTPZ-UHFFFAOYSA-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
ATC code	D01AA07 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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]

References

Gordee, R. S.; Matthews, T. R. (1969). "Systemic antifungal activity of pyrrolnitrin". Applied Microbiology. 17 (5): 690–694. PMC 377781. PMID 5785951.
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.
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.
Pillonel, Ch; Knauf-beiter, G.; Steinemann, A. (2003). "Encyclopedia of Agrochemicals". doi:10.1002/047126363X.agr106. ISBN 047126363X. Cite journal requires |journal= (help); |chapter= ignored (help)
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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[1] Gordee, R. S.; Matthews, T. R. (1969). "Systemic antifungal activity of pyrrolnitrin". Applied Microbiology. 17 (5): 690–694. 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.

[PillonelKnauf-beiter2003-4] Pillonel, Ch; Knauf-beiter, G.; Steinemann, A. (2003). "Encyclopedia of Agrochemicals". doi:10.1002/047126363X.agr106. ISBN 047126363X. Cite journal requires |journal= (help); |chapter= ignored (help)

[JespersDavidse1993-5] 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.