The project aims to expand the chemical space of non-proteinogec amino acids (NPAAs) that could modulate peptide conformation in a defined and predictable way. This will be achieved by: (i) the synthesis of NPAAs derived from carbohydrates, carbasugars and heteroaromatic compounds, (ii) the synthesis of peptides with incorporated NPAAs and their structural characterization, and (iii) the determination of the non-covalent interactions involving NPAAs that are responsible for the adoption of a particular secondary structure. The inspiration for NPAAs is found in natural compounds equipped with well-defined three-dimensional scaffolds. The envisaged methodology is based on the chemical transformation of carbohydrates, carbasugars and heteroaromatic compounds into related amino acids. We anticipate that peptides with such NPAAs will adopt conformationally distinct secondary structures. We plan to determine the role of structure, stereochemistry and non-covalent interactions responsible for their stabilization.