Ophthalmic acid

Ophthalmic acid^[1]

Names
IUPAC name (N-(L-γ-glutamyl)-(2S)-2-aminobutyryl)-glycine
Identifiers
CAS Number	495-27-2
ChEBI	CHEBI:84058
ChemSpider	5381695
Jmol interactive 3D	Image
MeSH	ophthalmic+acid
PubChem	7018721
InChI InChI=1S/C11H19N3O6/c1-2-7(10(18)13-5-9(16)17)14-8(15)4-3-6(12)11(19)20/h6-7H,2-5,12H2,1H3,(H,13,18)(H,14,15)(H,16,17)(H,19,20)/t6-,7-/m0/s1 Key: JCMUOFQHZLPHQP-BQBZGAKWSA-N
SMILES CC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O
Properties
Chemical formula	C11H19N3O6
Molar mass	289.29 g·mol^−1
Appearance	Colorless crystals
Related compounds
Related alkanoic acids	N-acetylaspartylglutamic acid glycylglycine alpha-Aminobutyric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. 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:10.1074/jbc.M601876200. PMID 16608839.

See also

• Aminobutyrate
• Glutathione
• Glutathione synthetase deficiency
• Oxidative stress