Tabtoxinine β-lactam

Tabtoxinine β-lactam
Names
	Systematic IUPAC name (2S)-2-Amino-4-[(3S)-3-hydroxy-2-oxoazetidin-3-yl]butanoic acid
	Other names (αS,3S)-α-Amino-3-hydroxy-2-oxo-3-azetidinebutanoic acid; (−)-Tabtoxinine β-lactam
Identifiers
CAS Number	65709-93-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	24751854;
PubChem CID	3035052;
UNII	2UUE5D9555 ;
CompTox Dashboard (EPA)	DTXSID80984253 ;
	InChI InChI=1S/C7H12N2O4/c8-4(5(10)11)1-2-7(13)3-9-6(7)12/h4,13H,1-3,8H2,(H,9,12)(H,10,11)/t4-,7-/m0/s1 Key: BSUXZTMOMIFYBF-FFWSUHOLSA-N;
	SMILES C1[C@](C(=O)N1)(CC[C@@H](C(=O)O)N)O;
Properties
Chemical formula	C7H12N2O4
Molar mass	188.183 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

Tabtoxinine β-lactam is a monobactam antibiotic derived from tabtoxin. Unlike other β-lactam antibiotics, which inhibit penicillin-binding proteins, tabtoxinine β-lactam inhibits glutamine synthetase.^[1]

References

^ Thomas, M. D.; Langston-Unkefer, P. J.; Uchytil, T. F.; Durbin, R. D. (1983). "Inhibition of Glutamine Synthetase from Pea by Tabtoxinine-β-lactam". Plant Physiology. 71 (4): 912–915. doi:10.1104/pp.71.4.912. PMC 1066143. PMID 16662928.

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