Tabtoxinine β-lactam

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]

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
3D model (JSmol)
ChemSpider
UNII
  • 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
  • C1[C@](C(=O)N1)(CC[C@@H](C(=O)O)N)O
Properties
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

References
  1. 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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