Cyclohexyloxycarbonyl based orthogonal solid phase peptide synthesis in Boc chemistry

Article abstract of DOI:10.1016/S0040-4020(98)00360-3

Application of N-cyclohexyloxocarbonyl (Choc) protection in Boc chemistry on solid phase provides a new possibility for the preparation of protected peptide fragments. A Choc/OcHex protection scheme allows also the assembly of cyclic lactam peptides linked to the resin through the C- terminus. Choc protection is stable under the 1M TMSOTf-thioanisole/TFA cleavage condition at 0°C, but it is removable by anhydrous HF. We have utilized cyclohexyloxycarbonyl as an orthogonal protecting group for the synthesis of a i) bicyclic epitope peptide of glycoprotein D of HSV 1 on BHA resin and ii) fully protected hexapeptide involved in protein transport on Merrifield resin.