Process for the synthesis of acylated derivatives of fatty acid-transporting thiols and in particular acyl-coenzymes A and the thus obtained acyl-coenzymes A

US5519128A · kind A · utility

Assignee

• COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES · FR

Inventors

• Jean-Paul Lellouche · Les Ulis, FR
• Karine Levannier · Rueil-Malmaison, FR
• Charles Mioskowski · Strasbourg, FR

Key dates

• Filing date: Feb 22, 1995
• Grant date: May 21, 1996
• Expiry date: Feb 22, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/20
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to a process for the synthesis of an acylated derivative of a fatty acid-transporting thiol such as the coenzyme A. According to this process, a silylated or stannylated thiol is prepared by reacting the thiol with a silylation or stannylation reagent in order to at least partly replace the unstable hydrogens of the thiol by SiR.sub.3 or SnR.sub.3 groups with R being an alkyl or aryl group. The silylated or stannylated thiol is then reacted in an anhydrous organic medium with an activated organic acid and a deprotection reagent able to eliminate the silyl or stannyl groups. In this way it is possible to obtain acylated derivatives of the coenzyme A, in which the acyl group can have up to 30 carbon atoms with high yields.