| 词条 | Ovothiol A |
| 释义 |
| ImageFile = Ovothiol A.svg | ImageSize = | ImageAlt = | IUPACName = (2S)-2-Amino-3-(3-methyl-5-sulfanylimidazol-4-yl)propanoic acid | OtherNames = 1-N-Methyl-4-mercaptohistidine | Section1 = {{Chembox Identifiers | CASNo = 108418-13-9 | PubChem = 130131 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 83318 | SMILES = CN1C=NC(=C1C[C@@H](C(=O)O)N)S | ChemSpiderID = 115159 | 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 | InChIKey = XWKKYVJREGXHFO-BYPYZUCNBB | StdInChI = 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 | StdInChIKey = XWKKYVJREGXHFO-BYPYZUCNSA-N | RTECS = | MeSHName = C061475 }} | Section2 = {{Chembox Properties | C=7|H=11|N=3|O=2|S=1 | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}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. References1. ^{{cite journal |author1=Turner, E. |author2=Klevit, R. |author3=Hager, L. J. |author4=Shapiro, B. M. |lastauthoramp=yes | title = Ovothiols, a family of redox-active mercaptohistidine compounds from marine invertebrate eggs | journal = Biochemistry | volume = 26 | issue = 13 | pages = 4028–4036 | date=1987| pmid = 3651433 | doi=10.1021/bi00387a043}} 2. ^{{cite journal |author1=Turner, E. |author2=Hager, L. J. |author3=Shapiro, B. M. |lastauthoramp=yes | title = Ovothiol replaces glutathione-peroxidase as a hydrogen-peroxide scavenger in sea-urchin eggs | journal = Science | volume = 242 | issue = 4880 | pages = 939–941 | date = 1988| pmid = 3187533 | doi=10.1126/science.3187533}} 3. ^{{cite journal | title = Thiols of intracellular pathogens. Identification of ovothiol A in Leishmania donovani and structural analysis of a novel thiol from Mycobacterium bovis |author1=Spies, H.S. |author2=Steenkamp, D.J. |lastauthoramp=yes |journal = Eur. J. Biochem. |date = 1994 |volume = 224 |issue = 1 |pages = 203–213 |pmid = 8076641 |doi=10.1111/j.1432-1033.1994.tb20013.x}} 3 : Thiols|Amino acids|Imidazoles |
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