Phosalacine

Phosalacine is a natural antimicrobial and herbicidal compound that has been isolated from the Actinobacteria Kitasatosporia phosalacinea.^[1]

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
CAS Number	92567-89-0
3D model (JSmol)	Interactive image
ChemSpider	62917600
PubChem CID	13564971
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/s1 Key: GRIZBDACBCXJCF-DCAQKATOSA-N
SMILES C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)O)NC(=O)[C@H](CCP(=O)(C)O)N
Properties
Chemical formula	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

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.