Ophthalmic acid

Structural formula
General
Surname	Ophthalmic acid
other names	γ-glutamyl-α-amino-n-butyryl-glycine; Ophthalmat;
Molecular formula	C 11 H 19 N 3 O 6
External identifiers / databases
PubChem	7018721
Wikidata	Q7098084
properties
Molar mass	289.29 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ophthalmic acid is a chemical compound from the group of tripeptides . It is structurally related to glutathione .

Occurrence

Ophthalmic acid occurs naturally in the lenses of the eyes and in the brains of cattle, rabbits and other animals (also together with norophthalmic acid ). It was discovered by SG Waley in 1956. It inhibits the activity of γ-glutamyl-cysteine synthetase and glyoxylase I as well as the breakdown of insulin in adipose tissue sections of rats. It is an oxidative stress biomarker that indicates the consumption of glutathione. The compound is biosynthesized starting from 2-aminobutyrate .

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Hugh Davson: The Eye Pt IB . Elsevier, 2012, ISBN 0-323-16212-6 , pp. 251 ( limited preview in Google Book search).
↑ Theodor Wieland, Miklos Bodanszky: The World of Peptides A Brief History of Peptide Chemistry . Springer Science & Business Media, 2012, ISBN 978-3-642-75850-8 , p. 18 ( limited preview in Google Book search).
↑ Spektrum.de: Ophthalmic Acid - Lexicon of Biochemistry , accessed on May 8, 2016
↑ Hans-Dieter Jakubke, Norbert Sewald: Peptides from A to ZA Concise Encyclopedia . John Wiley & Sons, 2008, ISBN 3-527-62117-2 , pp. 252 ( limited preview in Google Book search).
↑ T. Soga, R. Baran, M. Suematsu, Y. Ueno, S. Ikeda, T. Sakurakawa, Y. Kakazu, T. Ishikawa, M. Robert, T. Nishioka, M. Tomita: Differential metabolomics reveals ophthalmic acid as an oxidative stress biomarker indicating hepatic glutathione consumption. In: J. Biol. Chem. 281, 2006, pp. 16768-16776, PMID 16608839 .
↑ Wanda M. Haschek, Colin G. Rousseaux, Matthew A. Wallig: Haschek and Rousseaux's Handbook of Toxicologic Pathology . Academic Press, 2013, ISBN 978-0-12-415765-1 , pp. 388 ( limited preview in Google Book search).

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Hugh_Davson-2] Hugh Davson: The Eye Pt IB . Elsevier, 2012, ISBN 0-323-16212-6 , pp. 251 ( limited preview in Google Book search).

[Theodor_Wieland,_Miklos_Bodanszky-3] Theodor Wieland, Miklos Bodanszky: The World of Peptides A Brief History of Peptide Chemistry . Springer Science & Business Media, 2012, ISBN 978-3-642-75850-8 , p. 18 ( limited preview in Google Book search).

[spektrum.de-4] Spektrum.de: Ophthalmic Acid - Lexicon of Biochemistry , accessed on May 8, 2016

[Hans-Dieter_Jakubke,_Norbert_Sewald-5] Hans-Dieter Jakubke, Norbert Sewald: Peptides from A to ZA Concise Encyclopedia . John Wiley & Sons, 2008, ISBN 3-527-62117-2 , pp. 252 ( limited preview in Google Book search).

[PMID16608839-6] T. Soga, R. Baran, M. Suematsu, Y. Ueno, S. Ikeda, T. Sakurakawa, Y. Kakazu, T. Ishikawa, M. Robert, T. Nishioka, M. Tomita: Differential metabolomics reveals ophthalmic acid as an oxidative stress biomarker indicating hepatic glutathione consumption. In: J. Biol. Chem. 281, 2006, pp. 16768-16776, PMID 16608839 .

[Wanda_M._Haschek,_Colin_G._Rousseaux,_Matthew_A._Wallig-7] Wanda M. Haschek, Colin G. Rousseaux, Matthew A. Wallig: Haschek and Rousseaux's Handbook of Toxicologic Pathology . Academic Press, 2013, ISBN 978-0-12-415765-1 , pp. 388 ( limited preview in Google Book search).