Chemistry:Pyrrolnitrin
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| Preferred IUPAC name
3-Chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole | |
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3D model (JSmol)
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| KEGG | |
| MeSH | D011764 |
PubChem CID
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| Properties | |
| C10H6Cl2N2O2 | |
| Molar mass | 257.07284 |
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| 1=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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Tracking categories (test):
Pyrrolnitrin is a phenylpyrrole chemical used an antifungal antibiotic.[1] Pseudomonas pyrrocinia and other Pseudomonas species produce pyrrolnitrin from tryptophan as secondary metabolite.[2][3]
The synthetic 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. doi:10.1128/AEM.17.5.690-694.1969. 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. 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). "Fungicides, Phenylpyrroles". Encyclopedia of Agrochemicals. doi:10.1002/047126363X.agr106. ISBN 047126363X.
- ↑ 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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