Synthesis and Studies of Bulky Cycloalkyl α, β-Dehydroamino Acids that Enhance Proteolytic Stability

Three new bulky cycloalkyl alpha, beta-dehydroamino acids (Delta AAs) have been designed and synthesized. Each residue enhances the rigidity of model peptides and their stability to proteolysis, with larger ring sizes exhibiting greater effects. Peptides containing bulky cycloalkyl Delta AAs are inert to conjugate addition by a nucleophilic thiol. The results suggest that these residues will be effective tools for improving the proteolytic stability of bioactive peptides.

Automated summary

Three new bulky cycloalkyl alpha, beta-dehydroamino acids have been synthesized, which enhance the rigidity of model peptides and their stability to proteolysis. Larger ring sizes have greater effects. Peptides containing these bulky cycloalkyl Delta AAs are inert to conjugate addition by a nucleophilic thiol, suggesting their potential as effective tools for improving the proteolytic stability of bioactive peptides.