Ovothiol C

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H597338

CAS#: 105496-34-2

Description: Ovothiol C confers NAD(P)H-O2 oxidoreductase activity on ovoperoxidase; from sea urchin eggs.

Chemical Structure

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Ovothiol C
CAS# 105496-34-2
Instruction

Theoretical Analysis

Hodoodo Cat#: H597338
Name: Ovothiol C
CAS#: 105496-34-2
Chemical Formula: C9H15N3O2S
Exact Mass: 229.09
Molecular Weight: 229.290
Elemental Analysis: C, 47.14; H, 6.59; N, 18.33; O, 13.95; S, 13.98

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Ovothiol C; Ovothiol;

IUPAC/Chemical Name: (S)-2-(dimethylamino)-3-(4-mercapto-1-methyl-1H-imidazol-5-yl)propanoic acid

InChi Key: ONAWDGXCZMVYMN-ZETCQYMHSA-N

InChi Code: InChI=1S/C9H15N3O2S/c1-11(2)7(9(13)14)4-6-8(15)10-5-12(6)3/h5,7,15H,4H2,1-3H3,(H,13,14)/t7-/m0/s1

SMILES Code: O=C(O)[C@H](CC1=C(S)N=CN1C)N(C)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 229.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Song H, Her AS, Raso F, Zhen Z, Huo Y, Liu P. Cysteine oxidation reactions catalyzed by a mononuclear non-heme iron enzyme (OvoA) in ovothiol biosynthesis. Org Lett. 2014 Apr 18;16(8):2122-5. doi: 10.1021/ol5005438. Epub 2014 Mar 31. PubMed PMID: 24684381; PubMed Central PMCID: PMC3998768.

2: Song H, Leninger M, Lee N, Liu P. Regioselectivity of the oxidative C-S bond formation in ergothioneine and ovothiol biosyntheses. Org Lett. 2013 Sep 20;15(18):4854-7. doi: 10.1021/ol402275t. Epub 2013 Sep 9. PubMed PMID: 24016264; PubMed Central PMCID: PMC4166525.

3: De Luna P, Bushnell EA, Gauld JW. A density functional theory investigation into the binding of the antioxidants ergothioneine and ovothiol to copper. J Phys Chem A. 2013 May 16;117(19):4057-65. doi: 10.1021/jp402514w. Epub 2013 May 2. PubMed PMID: 23590643.

4: Braunshausen A, Seebeck FP. Identification and characterization of the first ovothiol biosynthetic enzyme. J Am Chem Soc. 2011 Feb 16;133(6):1757-9. doi: 10.1021/ja109378e. Epub 2011 Jan 19. PubMed PMID: 21247153.

5: Hand CE, Taylor NJ, Honek JF. Ab initio studies of the properties of intracellular thiols ergothioneine and ovothiol. Bioorg Med Chem Lett. 2005 Mar 1;15(5):1357-60. PubMed PMID: 15713386.

6: Bailly F, Azaroual N, Bernier JL. Design, synthesis and glutathione peroxidase-like properties of ovothiol-derived diselenides. Bioorg Med Chem. 2003 Oct 15;11(21):4623-30. PubMed PMID: 14527559.

7: Vamecq J, Maurois P, Bac P, Bailly F, Bernier JL, Stables JP, Husson I, Gressens P. Potent mammalian cerebroprotection and neuronal cell death inhibition are afforded by a synthetic antioxidant analogue of marine invertebrate cell protectant ovothiols. Eur J Neurosci. 2003 Sep;18(5):1110-20. PubMed PMID: 12956711.

8: Bailly F, Zoete V, Vamecq J, Catteau JP, Bernier JL. Antioxidant actions of ovothiol-derived 4-mercaptoimidazoles: glutathione peroxidase activity and protection against peroxynitrite-induced damage. FEBS Lett. 2000 Dec 1;486(1):19-22. PubMed PMID: 11108835.

9: Weldrick DP, Chodacka B, Vogt R, Steenkamp DJ. The effect of buthionine sulfoximine on the growth of Leishmania donovani in culture. FEMS Microbiol Lett. 1999 Apr 1;173(1):139-46. PubMed PMID: 10220890.

10: Marjanovic B, Simic MG, Jovanovic SV. Heterocyclic thiols as antioxidants: why ovothiol C is a better antioxidant than ergothioneine. Free Radic Biol Med. 1995 Apr;18(4):679-85. PubMed PMID: 7750792.

11: Holler TP, Hopkins PB. Ovothiols. Methods Enzymol. 1995;252:115-23. PubMed PMID: 7476344.

12: Shapiro BM. The control of oxidant stress at fertilization. Science. 1991 Apr 26;252(5005):533-6. PubMed PMID: 1850548.

13: Shapiro BM, Hopkins PB. Ovothiols: biological and chemical perspectives. Adv Enzymol Relat Areas Mol Biol. 1991;64:291-316. Review. PubMed PMID: 2053468.

14: Holler TP, Hopkins PB. Ovothiols as free-radical scavengers and the mechanism of ovothiol-promoted NAD(P)H-O2 oxidoreductase activity. Biochemistry. 1990 Feb 20;29(7):1953-61. PubMed PMID: 2331475.

15: Turner E, Hager LJ, Shapiro BM. Ovothiol replaces glutathione peroxidase as a hydrogen peroxide scavenger in sea urchin eggs. Science. 1988 Nov 11;242(4880):939-41. PubMed PMID: 3187533.

16: Shapiro BM, Turner E. Oxidative stress and the role of novel thiol compounds at fertilization. Biofactors. 1988 Jan;1(1):85-8. Review. PubMed PMID: 3076434.

17: Turner E, Klevit R, Hager LJ, Shapiro BM. Ovothiols, a family of redox-active mercaptohistidine compounds from marine invertebrate eggs. Biochemistry. 1987 Jun 30;26(13):4028-36. PubMed PMID: 3651433.

18: Turner E, Klevit R, Hopkins PB, Shapiro BM. Ovothiol: a novel thiohistidine compound from sea urchin eggs that confers NAD(P)H-O2 oxidoreductase activity on ovoperoxidase. J Biol Chem. 1986 Oct 5;261(28):13056-63. PubMed PMID: 3759947.