Abstract
Peptide coupling with minimal protection is one of the desired methods for the synthesis of peptides and proteins. To achieve regioselective amide bond formation, side chain protection is often essential; however, protecting groups potentially diminish peptide solubility and render the polar polyamide chain amphipathic due to their apolar nature. In this manuscript, we describe a new protecting group, N,N-dimethylaminoxy carbonyl (Dmaoc), and its use in peptide coupling reactions. The Dmaoc group has a relatively polar character compared to the Boc group, which is a conventional protecting group for the Nε-amine of Lys residues. This polar protecting group is removable by reduction in the buffer containing (±)-dithiothreitol (DTT). Furthermore, the Dmaoc group proved compatible with peptide ligation strategies featuring the activation of N-acyl diaminobenzamides (Dbz) with sodium nitrate to generate the respective benzotriazole leaving group. The Dmaoc/Dbz strategy described in this manuscript provides a new method for the chemical synthesis of peptides.
Highlights
Peptide coupling reactions are essential for the chemical synthesis of polypeptides and proteins (Kricheldorf, 2006; Kent, 2017)
In order to perform a peptide coupling reaction, we focused on the Dbz group that was known as a precursor of the Bt group
We reported the dimethylaminoxy carbonyl (Dmaoc) as a polar protecting group and its use in peptide coupling reactions
Summary
Peptide coupling reactions are essential for the chemical synthesis of polypeptides and proteins (Kricheldorf, 2006; Kent, 2017). The utility of the minimum protection strategy for peptide coupling was demonstrated in the chemical synthesis of proteins using the thioester leaving group (Aimoto, 1999). The protection of the Nε-amine of Lys residues with the iNoc group has demonstrated its utility during peptide synthesis (Asahina et al, 2015).
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