Ophthalmic acid

Ophthalmic acid[1]

Names
IUPAC name

(N-(L-γ-Glutamyl)-(2S)-2-aminobutyryl)glycine

Identifiers

CAS Number

* 495-27-2 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:84058 N

ChemSpider |

* 5381695 Y

MeSH | ophthalmic+acid

PubChem CID

* 7018721

UNII |

* 3A60475Q1Q Y

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 Y

Key: JCMUOFQHZLPHQP-BQBZGAKWSA-N Y

SMILES

* CC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O

Properties

Chemical formula

| C11H19N3O6
Molar mass | 289.288 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).

N verify (what is YN ?)
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 et al. (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.

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*[CID]: Compound ID