Safety-catch anchoring linkage for synthesis of peptide amides by Boc/Fmoc strategy

Article abstract of DOI:10.1016/S0040-4039(00)79406-8

2-Methoxy-4,4'-bis(methylthio)benhydrylamine (10) and the corresponding disulfoxide were prepared and tested as a model amide protecting groups for their stability toward acidic conditions. Subsequently, the novel 4-[4,4'-bis(methylsulfinyl)-2-oxy-(9-fluorenylmethyloxycarbonyl) benzhydrylamino]butanoic acid (SCAL) handle (9) has been prepared and applied to solid-phase peptide synthesis of C-terminal peptide amide using both 9-fluorenylmethyloxycarbonyl (Fmoc) and tert-butyloxycarbonyl (Boc) groups for N(α)-amino protection.