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Ophthalmic acid

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Ophthalmic acid

Ophthalmic acid[1]
Stereo, skeletal formula of ophthalmic acid
Names
IUPAC name
(N-(L-γ-glutamyl)-(2S)-2-aminobutyryl)-glycine
Identifiers
 N
ChEBI  N
ChemSpider  YesY
Jmol-3D images Image
MeSH
PubChem
Properties
C11H19N3O6
Molar mass 289.29 g·mol−1
Appearance Colorless crystals
Related compounds
Related alkanoic acids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

Ophthalmic acid, also known as ophthalmate (chemically L-γ-glutamyl-L-α-aminobutyrylglycine), is a tripeptide analogue of glutathione in which the cysteine group is replaced by L-2-aminobutyrate. It was first discovered and isolated from calf lens.[2]

Biosynthesis

Recent studies have shown that the ophthalmate can be biologically synthesized from 2-amino butyric acid through consecutive reactions with gamma-glutamylcysteine synthetase and glutathione synthetase. So the ophthalmic acid could be used as a biomarker in oxidative stress where the depletion of glutathione takes place.[3]

References

  1. ^ Ophthalmic acid
  2. ^ Waley SG; Biochem. J. 64, 715 (1956).
  3. ^

See also


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