Glutaurine

Glutaurine is an endogenous dipeptide which is an amide formed from glutamic acid and taurine.

Glutaurine
Names
IUPAC name
N5-(2-Sulfoethyl)-L-glutamine
Systematic IUPAC name
(2S)-2-Amino-5-oxo-5-[(2-sulfoethyl)amino]pentanoic acid
Other names
γ-Glutamyltaurine; γ-GT; γ-L-Glutamyltaurine[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C7H14N2O6S/c8-5(7(11)12)1-2-6(10)9-3-4-16(13,14)15/h5H,1-4,8H2,(H,9,10)(H,11,12)(H,13,14,15)/t5-/m0/s1
    Key: WGXUDTHMEITUBO-YFKPBYRVSA-N
  • InChI=1/C7H14N2O6S/c8-5(7(11)12)1-2-6(10)9-3-4-16(13,14)15/h5H,1-4,8H2,(H,9,10)(H,11,12)(H,13,14,15)/t5-/m0/s1
    Key: WGXUDTHMEITUBO-YFKPBYRVBF
  • O=C(NCCS(=O)(=O)O)CC[C@@H](C(=O)O)N
Properties
C7H14N2O6S
Molar mass 254.26
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Biological role

Glutaurine is an antiepileptic with antiamnesia properties. Glutaurine was discovered in the parathyroid in 1980, and later in the mammalian brain. This led to studies on intrinsic and synthetic taurine peptides, and the suggestion that γ-glutamyltransferase (GGT; γ-glutamyl-transpeptidase) in the brain is responsible for its in vivo formation.[2]

The versatile molecule mimics the anxiolytic drug diazepam, and is implicated in phenomena from feline aggression to amphibian metamorphosis, radiation protection, and the glutamatergic system in schizophrenic disorders.[2]

References
  1. "56488-60-9 CAS Manufactory". Chemicalbook.com. Retrieved 2012-04-21.
  2. Bittner, S.; Win, T.; Gupta, R. (2005). "γ-L-glutamyltaurine". Amino Acids. 28 (4): 343–356. doi:10.1007/s00726-005-0196-7. PMID 15838590. S2CID 209532290.
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