Pyrroloisoquinoline-based tetrapeptide analogues mimicking reverse-turn secondary structures

(Chemical Equation Presented) New pyrroloisoquinoline-based tetrapeptides were synthesized in enantiomerically pure form, and their conformational features were studied by NMR, IR, and molecular-modeling techniques. The presence of a reverse turn was observed in both structures, with the C1 stereochemistry playing a central role in determining stable conformations. In particular, all of the analyses led to the conclusion that a type II′ β-turn is mostly stabilized in tetrapeptide mimic 3a, while a typical inverse γ-turn geometry is revealed for the diastereoisomer 3b.