Mechanistic and stereochemical investigation of fatty acid and polyketide biosynthesis using chiral malonates

Abstract

Chiral malonates, ( R)-[1- 13C;2- 2H]malonate and ( S)-[1- 13C;2- 2H]malonate, were synthesised and characterised as malonyl-CoA derivatives with yeast fatty acid synthase using mass spectrometric analysis of the palmitic acid produced. The chiral malonates were used to investigate the steric course of fatty acid synthase from rat liver and the fatty acid synthase and 6-methylsalicylic acid synthase from Penicillium patulum.