Amino acids and peptides. Part 38. Development of a new amino-protecting group, 2-adamantyloxycarbonyl, and its application to peptide synthesis

A new ε-amino protecting group, 2-adamantyloxycarbonyl (2-Adoc), was developed, and its application to the solid-phase synthesis of protected peptides was demonstrated in combination with Nα-fluoren-9-ylmethoxycarbonyl (Fmoc) protection and trifluoroacetic acid (TFA)-cleavable resin support. The 2-Adoc group was applied successfully also to the solution-phase peptide synthesis depending on tert-butoxycarbonyl (Boc)-chemistry.