Arsinothricin

Arsinothricin
Clinical data
Drug class	glutamine synthetase inhibitor
Identifiers
	IUPAC name 2-amino-4-[hydroxy(methyl)arsoryl]butanoic acid;
CAS Number	2267352-87-2;
PubChem CID	170988177;
PDB ligand	BLJ (PDBe, RCSB PDB);
Chemical and physical data
Formula	C5H12AsNO4
Molar mass	225.076 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[As](=O)(CCC(C(=O)O)N)O;
	InChI 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.^[1]^[2] 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,^[3] arsinothricin is unusual as a pentavalent arsenical, displaying antibiotic activity with a novel mechanism of action.^[2]^[4]

References

^ Nadar VS, Chen J, Dheeman DS, Galván AE, Yoshinaga-Sakurai K, Kandavelu P, et al. (2019). "Arsinothricin, an arsenic-containing non-proteinogenic amino acid analog of glutamate, is a broad-spectrum antibiotic". Communications Biology. 2 131. doi:10.1038/s42003-019-0365-y. PMC 6465285. PMID 30993215.
^ ^a ^b Hoshino S, Onaka H, Abe I (April 2025). "Recent advances in the biosynthetic studies of bacterial organoarsenic natural products". Natural Product Reports. 42 (4): 663–671. doi:10.1039/d4np00036f. PMID 39192828.
^ Sattar A, Xie S, Hafeez MA, Wang X, Hussain HI, Iqbal Z, et al. (December 2016). "Metabolism and toxicity of arsenicals in mammals". Environmental Toxicology and Pharmacology. 48: 214–224. Bibcode:2016EnvTP..48..214S. doi:10.1016/j.etap.2016.10.020. PMID 27829199.
^ Howlader AH, Suzol SH, Nadar VS, Galván AE, Nedovic A, Cudic P, et al. (October 2021). "Chemical synthesis of the organoarsenical antibiotic arsinothricin". RSC Advances. 11 (56): 35600–35606. Bibcode:2021RSCAd..1135600H. doi:10.1039/d1ra06770b. PMC 9043123. PMID 35493177.