Chemistry:Phosalacine
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| IUPAC name
(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]-4-methylpentanoic acid
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| Other names
(2S)-2-Amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-leucine
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C14H28N3O6P | |
| Molar mass | 365.367 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
Phosalacine is a natural antimicrobial and herbicidal compound that has been isolated from the Actinobacteria Kitasatosporia phosalacinea.[1]
It is a tripeptide consisting of the amino acids glufosinate (phosphinothricin), alanine, and leucine.[2] It is similar in structure to bialaphos, differing by replacement of the terminal alanine with leucine.
Phosalacine has antimicrobial activity against Gram-positive and Gram-negative bacteria and some fungi.[1] It also shows herbicidal activity against alfalfa.[1] It is believed that the herbicidal activity is due to the slow release of glufosinate,[3] which is a commercially-used broad spectrum herbicide.
References
- ↑ 1.0 1.1 1.2 Omura, Satoshi; Murata, Masatsune; Hanaki, Hideaki; Hinotozawa, Kiyoizumi; Oiwa, Ruiko; Tanaka, Haruo (1984). "Phosalacine, a new herbicidal antibiotic containing phosphinothricin. Fermentation, isolation, biological activity and mechanism of action". The Journal of Antibiotics 37 (8): 829–835. doi:10.7164/antibiotics.37.829. PMID 6480502.
- ↑ Omura, Satoshi; Hinotozawa, Kiyoizumi; Imamura, Nobutaka; Murata, Masatsune (1984). "The structure of phosalacine, a new herbicidal antibiotic containing phosphinothricin". The Journal of Antibiotics 37 (8): 939–940. doi:10.7164/antibiotics.37.939. PMID 6480509.
- ↑ Hoagland, Robert E. (1988). "Naturally Occurring Carbon—Phosphorus Compounds as Herbicides". Biologically Active Natural Products. ACS Symposium Series. 380. pp. 182–210. doi:10.1021/bk-1988-0380.ch013. ISBN 9780841215566.
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