Chemistry Commons^™

Design, Synthesis, And Conformational Studies Of Peptides Containing α,α-Disubstituted Amino Acids, Jia Wang

LSU Doctoral Dissertations

C^α,α-disubstituted amino acids (ααAAs) are widely utilized to conformationally constrain peptides. Several pentapeptides containing dipropylglycine (Dpg) at alternating positions and their α-amino acid counterpart L-norvaline (Nva) analogues were synthesized to fully investigate the impact of Dpg on peptide backbone structure in aqueous solution. CD, VCD and NMR spectral analysis suggest that Dpg containing peptides adopt more ordered structures relative to their Nva containing analogues. The central residues (Ala, Thr, Tyr, Val) and the charged side-chains of Glu and Lys play important roles in the degree of peptide folding. Hydrophobic and branched residues (Val, Tyr) at the …