Arsinothricin

Arsinothricin
Clinical data
Drug classglutamine synthetase inhibitor
Identifiers
  • 2-amino-4-[hydroxy(methyl)arsoryl]butanoic acid
CAS Number
PubChem CID
PDB ligand
Chemical and physical data
FormulaC5H12AsNO4
Molar mass225.076 g·mol−1
3D model (JSmol)
  • C[As](=O)(CCC(C(=O)O)N)O
  • InChI=InChI=1S/C5H12AsNO4/c1-6(10,11)3-2-4(7)5(8)9/h4H,2-3,7H2,1H3,(H,8,9)(H,10,11)
  • Key:CXTQPLOKUBDLTK-UHFFFAOYSA-N

Arsinothricin is a naturally occurring organoarsenical antibiotic produced by the rhizosphere bacterium Burkholderia gladioli. Structurally, it is a non-proteinogenic amino acid analog of glutamate, in which the γ-carboxyl group is replaced by a methylarsenate moiety. Arsinothricin acts as a broad-spectrum antibiotic effective against a variety of bacterial pathogens, including multidrug-resistant species, through competitive inhibition of bacterial glutamine synthetase. Unlike many arsenic compounds that are highly toxic due to their trivalent state, arsinothricin is unusual as a pentavalent arsenical, displaying antibiotic activity with a novel mechanism of action.

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