1.6 Peptides and Chirality Effects on the Conformation and the Synthesis of Medicinally Relevant Peptides

Chirality plays a major role in the form and function of peptides, because their biological activity and physical properties are typically contingent on conformation, which is inherently controlled by the sequence and configuration of the amino acid components. Examining the effects of chirality on peptide secondary structure as well as the application of enantiomeric, diastereomeric and retro-enantiomeric sequences to investigate peptide biology, this review provides guidelines for studying chiral peptide sequences to define the importance of configuration and conformation on activity. Focusing on medicinally and industrially relevant targets, methodology is reviewed for addressing the issue of racemization during synthesis to prepare stereochemically defined peptide products.