108418-13-9

Basic information

• Product Name: ovothiol A
• Synonyms: ovothiol A
• CAS NO: 108418-13-9
• Molecular Formula: C7H11N3O2S
• Molecular Weight: 201.249
• Mol File: 108418-13-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 483.2°C at 760 mmHg
• Flash Point: 246.1°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 3.77E-10mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: ovothiol A(CAS DataBase Reference)
• NIST Chemistry Reference: ovothiol A(108418-13-9)
• EPA Substance Registry System: ovothiol A(108418-13-9)

Safety Data

• Hazardous Substances Data: 108418-13-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A L-histidine derivative that is L-histidine substituted at positions N3 and C5 on the imidazole ring by methyl and mercapto groups respectively.

InChI: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

Upstream product

• 62982-26-7 5-mercaptohistidine 
• 110117-70-9 5-(chloromethyl)-4-<<(4-methoxyphenyl)methyl>thio>-1-methyl-1H-imidazole hydrochloride 
• 110117-69-6 5-(hydroxymethyl)-4-<<(4-methoxyphenyl)methyl>thio>-1-methylimidazole 
• 110117-73-2 (S)-(4-methoxyphenyl)methyl-L-ovothiol A 
• 110117-72-1 (R)-3,6-Diethoxy-2-isopropyl-5-[5-(4-methoxy-benzylsulfanyl)-3-methyl-3H-imidazol-4-ylmethyl]-2,5-dihydro-pyrazine 
• 110117-72-1 (2R,5S)-3,6-Diethoxy-2-isopropyl-5-[5-(4-methoxy-benzylsulfanyl)-3-methyl-3H-imidazol-4-ylmethyl]-2,5-dihydro-pyrazine 
• 105372-70-1 imbricatine 

Downstream Products

• 73491-33-5 L-ovothiol A disulfide 

Relevant articles and documents

In Vitro Reconstitution of the Remaining Steps in Ovothiol A Biosynthesis: C-S Lyase and Methyltransferase Reactions

Ovothiols are thiolhistidine derivatives. The first step of ovothiol biosynthesis is OvoA-catalyzed oxidative coupling between histidine and cysteine. In this report, the remaining steps of ovothiol A biosynthesis were reconstituted in vitro. ETA-14770 (OvoB) was reported as a PLP-dependent sulfoxide lyase, responsible for mercaptohistidine production. OvoA was found to be a bifunctional enzyme, which mediates both oxidative C-S bond formation and methylation of mercaptohistidine to afford ovothiol A. Besides reconstituting the whole biosynthetic pathway, two unique features proposed in the literature were also examined: A potential cysteine-recycling mechanism of the C-S lyase (OvoB) and the selectivity of the ?-N methyltransferase.

Total Synthesis of Marine Mercaptohistidines: Ovothiols A, B, and C

Syntheses of ovothiols A and C in optically active form and ovothiols A and B in racemic form are reported.In all cases, synthesis of an S-protected mercaptoimidazole is followed by elaboration of an amino acid side chain.