Oligomers of α-aminoisobutyric acid were synthesized with varying lengths (n=2-8) and differing C-terminal chiral groups. The Aib residue is achiral and strongly helicogenic. Oligomers of Aib residues form 50/50 (racemic) mixtures of left-and right-handed helices. The synthetic schemes were based on the nucleophilicity of the N-terminal nitrogen, which is able to attack the C-terminal carbonyl—thereby creating new amide bonds. The peptides were carefully manipulated using a variety of reaction conditions and mechanisms, which include amide coupling, ester hydrolysis, and catalytic hydrogenolysis. By utilizing an organized combination of these reaction schemes, along with the characteristic amide-forming nucleophilic acyl substitution, desired peptides of differing lengths were created. Subsequently, attachment of a C-terminal chiral amine—which could contain the ability to bias the handedness of the peptide’s helix—was performed through similar nucleophilic acyl substitution. In order to investigate the degree of which the helices could be chirally influenced by the C-terminal amine, it is necessary to have developed a reaction scheme that supports the efficient synthesis of Aib peptides of multiple lengths. A combination of <sup>1</sup>H NMR and infrared spectroscopy, along with mass spectrometry, was engaged to confirm our syntheses after each step of the pathway.

Synthesis and spectroscopic confirmation of Aib peptides containing chiral C-terminus groups

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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