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Role Of Peptide Backbone Conformation On Biological Activity Of Chemotactic Peptides, Andrew R. Dentino, Periathamby A. Raj, Krishna K. Bhandary, Mark E. Wilson, Michael J. Devine

School of Dentistry Faculty Research and Publications

To investigate the role of peptide backbone conformation on the biological activity of chemotactic peptides, we synthesized a unique analog of N-formyl-Met-Leu-Phe-OH incorporating the C ^α,α disubstituted residue, dipropylglycine (Dpg) in place of Leu. The conformation of the stereochemically constrained Dpg analog was examined in the crystalline state by x-ray diffraction and in solution using NMR, IR, and CD methods. The secretagogue activity of the peptide on human neutrophils was determined and compared with that of a stereochemically constrained, folded type II β-turn analog incorporating 1-aminocyclohexanecarboxylic acid (Ac₆c) at position 2 (f-Met- Ac₆c -Phe-OMe), the …