4-(3-Hydroxy-4-methylpentyl)phenylacetic acid as a new linker for the solid phase synthesis of peptides with Boc chemistry

Article abstract of DOI:10.1016/S0040-4039(98)02316-8

The anchoring the first amino acid in Boc chemistry to a 4-(3-hydroxy- 4-methylpentyl)phenylacetic acid linker is described and compared to the conventional Pam resin. The peptidyl-4(4-methyl-3-pentoxy)phenylacetamide linkage is slightly more stable to TFA than the Pam linker but in contrast to the Pam linker stable to cleavage of benzylic protective groups with TFMSA/DMS/TFA mixtures. This allows a mild and convenient two step deprotection procedure using the 'low TFMSA-high HF'. In HF this new linker reacts preferentially in an intramolecular reaction forming a tetrahydronaphthalene derivative.