Synthesis of Peptides with the Formation of Highly Sterically Hindered Peptide Bonds

Key words

hindered peptide bonds - steric hindrance - alkylcysteines - amidonitriles

Significance

The introduction of unnatural amino acids, such as α,α-disubstituted α-amino acids, into peptide backbones is important in drug discovery and medicinal chemistry. The authors have developed a synthetic method for forming such highly hindered peptide bonds from α,α-disubstituted α-amidonitriles and N-alkylcysteines.

Comment

The method produced hindered peptide bonds in good yields. The reaction of α,α-disubstituted α-amidonitriles with N-alkylcysteines proceeds in the absence of a coupling reagent.

Publication History

Article published online:
18 August 2022