Phosalacine

Phosalacine
Names
IUPAC name
(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]-4-methylpentanoic acid
Other names
(2S)-2-Amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-leucine
Identifiers
3D model (JSmol)
ChemSpider
  • 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/s1
    Key: GRIZBDACBCXJCF-DCAQKATOSA-N
  • C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CCP(=O)(C)O)N
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).

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. ^ a b c 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.