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Phosalacine

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Phosalacine
Names
IUPAC name (2S)-2-butanoyl]amino]propanoyl]amino]-4-methylpentanoic acid
Other names (2S)-2-Amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-leucine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C14H28N3O6P/c1-8(2)7-11(14(20)21)17-12(18)9(3)16-13(19)10(15)5-6-24(4,22)23/h8-11H,5-7,15H2,1-4H3,(H,16,19)(H,17,18)(H,20,21)(H,22,23)/t9-,10-,11-/m0/s1Key: GRIZBDACBCXJCF-DCAQKATOSA-N
SMILES
  • C(C(=O)N(CC(C)C)C(=O)O)NC(=O)(CCP(=O)(C)O)N
Properties
Chemical formula C14H28N3O6P
Molar mass 365.367 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Phosalacine is a natural antimicrobial and herbicidal compound that has been isolated from the Actinobacteria Kitasatosporia phosalacinea.

It is a tripeptide consisting of the amino acids glufosinate (phosphinothricin), alanine, and leucine. 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. It also shows herbicidal activity against alfalfa. It is believed that the herbicidal activity is due to the slow release of glufosinate, which is a commercially-used broad spectrum herbicide.

References

  1. ^ 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.
  2. 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. S2CID 9186238.
  3. Hoagland, Robert E. (1988). "Naturally Occurring Carbon—Phosphorus Compounds as Herbicides". Biologically Active Natural Products. ACS Symposium Series. Vol. 380. pp. 182–210. doi:10.1021/bk-1988-0380.ch013. ISBN 9780841215566.
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