Ophthalmic acid
From Wikipedia, the free encyclopedia
| Ophthalmic acid | |
|---|---|
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| Identifiers | |
| CAS number | [495-27-2] |
| PubChem | |
| MeSH | |
| SMILES | O=C(NCC(O)=O)C(NC(=O)CCC(N)C(O)=O)CC |
| Properties | |
| Molecular formula | C11H19N3O6 |
| Molar mass | 289.285 |
| Appearance | Colorless solid |
| Melting point |
NA |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Contents |
[edit] 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]
[edit] 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]
[edit] References
- ^ Waley SG; Biochem. J. 64, 715 (1956).
- ^ Metabolomics Toolbox: Ophthalmic acid
- ^ 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:.
