Protection of hydroxy groups by silylation: use in peptide synthesis and as lipophilicity modifiers for peptides

Abstract

A survey of a series of organosilyl derivatives of serine and tyrosine has shown that they have a satisfactory stability profile for use in peptide synthesis. Only when alkaline conditions were used did side-reactions appear. A range of stability profiles have been determined from a study of organosilyl derivatised dipeptides under different conditions, giving t_½-values for hydrolysis ranging from 41 to 465 min in acid conditions, yet giving long-term stability at pH-values near to neutrality.