The (2-Phenyl-2-trimethylsilyl)ethyl(PTMSEL) Linker—A Novel Linker for the Solid-Phase Synthesis of Protected Peptides and Glycopeptides Cleavable with Fluoride This work was supported by the Volkswagen-Stiftung and by the Fonds der Chemischen Industrie. M.W. is grateful for a fellowship of the Boehringer-Ingelheim-Stiftung.

Abstract

Suitable for the immobilization of carboxylic acids, the (2-phenyl-2-trimethylsilyl)ethyl linker was developed as a novel, fluoride-sensitive anchor. Cleavage with tetrabutylammonium fluoride (TBAF) trihydrate in CH2Cl2 under almost neutral conditions gives the corresponding peptides and glycopeptides in high yields and purity without affecting aspartate structures and most of the common protecting groups in peptide chemistry (see scheme).