73491-33-5

Upstream product

• 62982-26-7 5-mercaptohistidine 
• 110117-72-1 (R)-3,6-Diethoxy-2-isopropyl-5-[5-(4-methoxy-benzylsulfanyl)-3-methyl-3H-imidazol-4-ylmethyl]-2,5-dihydro-pyrazine 
• 105372-70-1 imbricatine 
• 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 
• 110117-69-6 5-(hydroxymethyl)-4-<<(4-methoxyphenyl)methyl>thio>-1-methylimidazole 
• 108418-13-9 L-ovothiol A 
• 110117-70-9 5-(chloromethyl)-4-<<(4-methoxyphenyl)methyl>thio>-1-methyl-1H-imidazole hydrochloride 
• 110117-73-2 (S)-(4-methoxyphenyl)methyl-L-ovothiol A 

Relevant academic research and scientific papers

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.