Stereoselective synthesis of 1- O-β-feruloyl and 1- O-β-sinapoyl glucopyranoses

Abstract

1- O-β-Feruloyl and 1- O-β-sinapoyl glucopyranoses are two common substrates for serine carboxypeptidase-like acyltransferases and serve as acyl donors in the biosynthesis of numerous secondary metabolites. In addition, they are involved in plant cell wall cross-linking and are also ideal substrates for studying the kinetics of lignification involving hydroxycinnamates. We report the first chemical (and multi-gram scale) synthesis of 1- O-β-feruloyl and 1- O-β-sinapoyl glucopyranoses.