Chemo- and Site-Selective Replacement of N-Terminal Carbamates in Peptides

In peptide synthesis, it is important to distinguish the terminal amino group and carry out the selective trans-formation of only the N-terminal protecting group. We describe herein a reaction for the chemo-and site-selective replacement of carbamates with various other carbamates only at the N-terminus of peptides. We demonstrate the scope of carbamates and peptides and the introduction of fluorine into a peptide. This strategy is applicable to the late stage of peptide synthesis.

Automated summary

This article presents an important reaction in peptide synthesis, which distinguishes the terminal amino group and selectively transforms only the N-terminal protecting group. Furthermore, this strategy is applicable to the late stage of peptide synthesis and allows for the introduction of fluorine into peptides.