Ophthalmic acid

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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]

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. ^ Waley SG; Biochem. J. 64, 715 (1956).
2. ^ http://www.hmdb.ca/scripts/show_card.cgi?METABOCARD=HMDB05765.txt
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

• Glutathione synthetase deficiency
• Oxidative stress

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