Ovothiol A

Last updated
Ovothiol A
Ovothiol A.svg
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
3D model (JSmol)
ChEBI
ChemSpider
MeSH C061475
PubChem CID
UNII
  • 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
  • CN1C=NC(=C1C[C@@H](C(=O)O)N)S
Properties
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).

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

This thiol is also found in some human pathogens such as Trypanosoma cruzi and Leishmania donovani . [3]

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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