Acid-catalysed hydrolysis of prostacyclin: origin of the unused lability

Abstract

The extra lability (89 ×) of prostacyclin towards acid-catalysed hydrolysis of its vinyl ether functional group in aqueous solution at 25 °C is traced to the carboxylic acid residue of this molecule operating in its ionized form, either as an electrostatic catalyst or, upon prior protonation, as an intramolecular general acid catalyst.