Ophthalmic acid

Ophthalmic acid^[1]

Names
IUPAC name (N-(L-γ-Glutamyl)-(2S)-2-aminobutyryl)glycine
Identifiers
CAS Number	495-27-2
3D model (Jmol)	Interactive image
ChEBI	CHEBI:84058
ChemSpider	5381695
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 α-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 analog 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]

See also

• Aminobutyrate
• Glutathione
• Glutathione synthetase deficiency
• Oxidative stress

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 & 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.