My watch list  

Ophthalmic acid

Ophthalmic acid
CAS number 495-27-2
PubChem 193304
MeSH acid Ophthalmic acid
Molecular formula C11H19N3O6
Molar mass 289.285
Appearance Colorless solid
Melting point


Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references


Ophthalmic acid

Ophthalmic acid is a tripeptide, also known as ophthalmate (chemically L-Ύ-glutamyl-L-α-aminobutyrylglycine) is an analogue of glutathione in which the cysteine moiety is replaced by L-2-aminobutyrate. It was first discovered and isolated from calf lens.[1] The IUPAC name of ophthalmic acid is (2S)-2-amino-4-[[(2S)-2-aminobutanoyl]-(carboxymethyl)carbamoyl]butanoic acid.[2]


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]


  1. ^ Waley SG; Biochem. J. 64, 715 (1956).
  2. ^
  3. ^ Tomoyoshi Soga, Richard Baran, Makoto Suematsu, Yuki Ueno, Satsuki Ikeda, Tadayuki Sakurakawa, Yuji Kakazu, Takamasa Ishikawa, Martin Robert, Takaaki Nishioka, and Masaru Tomita (June 2006). "Differential Metabolomics Reveals Ophthalmic Acid as an Oxidative Stress Biomarker Indicating Hepatic Glutathione Consumption". Journal of Biological Chemistry 281 (24): 16768-16776. doi:doi:10.1074/jbc.M601876200.

See also

External links

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Ophthalmic_acid". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE