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Article

Aza-Amino Acids Disrupt β-Sheet Secondary Structures

by
Michael A. McMechen
†,
Evan L. Willis
†,
Preston C. Gourville
and
Caroline Proulx
*
Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA
*
Author to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Molecules 2019, 24(10), 1919; https://doi.org/10.3390/molecules24101919
Submission received: 1 May 2019 / Revised: 15 May 2019 / Accepted: 17 May 2019 / Published: 18 May 2019
(This article belongs to the Special Issue Advances in Peptide and Peptidomimetic Design Inspiring Basic Science and Drug Discovery: A Themed Issue Honoring Professor Victor J. Hruby on the Occasion of His 80th Birthday)
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Abstract

Cα to N substitution in aza-amino acids imposes local conformational constraints, changes in hydrogen bonding properties, and leads to adaptive chirality at the nitrogen atom. These properties can be exploited in mimicry and stabilization of peptide secondary structures and self-assembly. Here, the effect of a single aza-amino acid incorporation located in the upper β-strand at a hydrogen-bonded (HB) site of a β-hairpin model peptide (H-Arg-Tyr-Val-Glu-Val-d-Pro-Gly-Orn-Lys-Ile-Leu-Gln-NH2) is reported. Specifically, analogs in which valine3 was substituted for aza-valine3 or aza-glycine3 were synthesized, and their β-hairpin stabilities were examined using Nuclear Magnetic Resonance (NMR) spectroscopy. The azapeptide analogs were found to destabilize β-hairpin formation compared to the parent peptide. The aza-valine3 residue was more disruptive of β-hairpin geometry than its aza-glycine3 counterpart.
Keywords: peptidomimetics; azapeptides; aza-amino acids; β-hairpin; β-sheet peptidomimetics; azapeptides; aza-amino acids; β-hairpin; β-sheet
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MDPI and ACS Style

McMechen, M.A.; Willis, E.L.; Gourville, P.C.; Proulx, C. Aza-Amino Acids Disrupt β-Sheet Secondary Structures. Molecules 2019, 24, 1919. https://doi.org/10.3390/molecules24101919

AMA Style

McMechen MA, Willis EL, Gourville PC, Proulx C. Aza-Amino Acids Disrupt β-Sheet Secondary Structures. Molecules. 2019; 24(10):1919. https://doi.org/10.3390/molecules24101919

Chicago/Turabian Style

McMechen, Michael A., Evan L. Willis, Preston C. Gourville, and Caroline Proulx. 2019. "Aza-Amino Acids Disrupt β-Sheet Secondary Structures" Molecules 24, no. 10: 1919. https://doi.org/10.3390/molecules24101919

APA Style

McMechen, M. A., Willis, E. L., Gourville, P. C., & Proulx, C. (2019). Aza-Amino Acids Disrupt β-Sheet Secondary Structures. Molecules, 24(10), 1919. https://doi.org/10.3390/molecules24101919

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