Ovothiol A

Ovothiol A
Names
	Systematic IUPAC name (2S)-2-Amino-3-(1-methyl-4-sulfanyl-1H-imidazol-5-yl)propanoic acid
	Other names 1-N-Methyl-4-mercaptohistidine
Identifiers
CAS Number	108418-13-9 check;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:83318 check;
ChemSpider	115159;
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
MeSH	C061475
PubChem CID	130131;
UNII	BJK39KC2PD check;
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
	InChI InChI=1S/C7H11N3O2S/c1-10-3-9-6(13)5(10)2-4(8)7(11)12/h3-4,13H,2,8H2,1H3,(H,11,12)/t4-/m0/s1 Key: XWKKYVJREGXHFO-BYPYZUCNSA-N; InChI=1/C7H11N3O2S/c1-10-3-9-6(13)5(10)2-4(8)7(11)12/h3-4,13H,2,8H2,1H3,(H,11,12)/t4-/m0/s1 Key: XWKKYVJREGXHFO-BYPYZUCNBB;
	SMILES CN1C=NC(=C1C[C@@H](C(=O)O)N)S;
Properties
Chemical formula	C7H11N3O2S
Molar mass	201.24 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ovothiol A (N1-methyl-4-mercaptohistidine) is a highly reducing antioxidant mercaptohistidine, which accumulates to very high levels in the eggs of certain marine invertebrates, including sea urchins, scallops and starfish,^[1] where it acts to scavenge hydrogen peroxide released during fertilization.^[2]

This thiol is also found in some human pathogens including trypanosomes and members of the genus Leishmania.^[3]

It is synthesized by the addition and oxidation of cysteine to histidine by 5-histidylcysteine sulfoxide synthase, followed by methylation and further reduction.

References

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