Ovotiol A

Ovotiol A
Nama
Nama IUPAC (sistematis)
(2S)-2-Amino-3-(1-methyl-4-sulfanyl-1H-imidazol-5-yl)propanoic acid
Nama lain
1-N-Methyl-4-mercaptohistidine
Penanda
Model 3D (JSmol)
ChEBI
ChemSpider
Nomor EC
MeSH C061475
Nomor RTECS {{{value}}}
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
Sifat
C7H11N3O2S
Massa molar 201,24 g·mol−1
Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa).
Referensi

Ovotiol A (N1-metil-4-merkaptohistidina) adalah antioksidan dengan daya reduksi yang sangat tinggi yang terakumulasi dalam kadar sangat tinggi pada telur beberapa invertebrata laut, termasuk bulu babi, kerang simping, dan bintang laut,[1] tempat senyawa ini berfungsi menetralkan hidrogen peroksida yang dilepaskan selama proses pembuahan.[2]

Antioksidan jenis tiol ini juga ditemukan pada beberapa patogen manusia, seperti Trypanosoma cruzi dan Leishmania donovani.[3]

Ovotiol A disintesis melalui penambahan dan oksidasi sisteina ke histidina oleh enzim 5-histidilsisteina sulfoksida sintase, yang kemudian diikuti oleh proses metilasi dan reduksi lebih lanjut.

Referensi

  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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