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Ovothiol A

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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
3D model (JSmol)
ChEBI
ChemSpider
MeSH C061475
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: XWKKYVJREGXHFO-BYPYZUCNBB
SMILES
  • CN1C=NC(=C1C(C(=O)O)N)S
Properties
Chemical formula C7H11N3O2S
Molar mass 201.24 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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, where it acts to scavenge hydrogen peroxide released during fertilization.

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

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

See also

References

  1. Turner, E.; Klevit, R.; Hager, L. J. & Shapiro, B. M. (1987). "Ovothiols, a family of redox-active mercaptohistidine compounds from marine invertebrate eggs". Biochemistry. 26 (13): 4028–4036. doi:10.1021/bi00387a043. PMID 3651433.
  2. Turner, E.; Hager, L. J. & Shapiro, B. M. (1988). "Ovothiol replaces glutathione-peroxidase as a hydrogen-peroxide scavenger in sea-urchin eggs". Science. 242 (4880): 939–941. Bibcode:1988Sci...242..939T. doi:10.1126/science.3187533. PMID 3187533. S2CID 5820883.
  3. Spies, H.S. & Steenkamp, D.J. (1994). "Thiols of intracellular pathogens. Identification of ovothiol A in Leishmania donovani and structural analysis of a novel thiol from Mycobacterium bovis". Eur. J. Biochem. 224 (1): 203–213. doi:10.1111/j.1432-1033.1994.tb20013.x. PMID 8076641.
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