Cyclohexyloxycarbonyl based orthogonal solid phase peptide synthesis in Boc chemistry
作者:Gábor Mezö、Nikolett Mihala、György Kóczán、Ferenc Hudecz
DOI:10.1016/s0040-4020(98)00360-3
日期:1998.6
Application of N-cyclohexyloxycarbonyl (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 degrees 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. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.