Novel peptide foldameric motifs: a step forward in our understanding of the fully-extended conformation/3(10)-helix coexistence

Organic & Biomolecular Chemistry
Fernando FormaggioClaudio Toniolo

Abstract

The fully-extended, multiple C(5), conformation or 2.0(5) helix is a very appealing peptide secondary structure, in particular for its potential use as a molecular spacer, as it is characterized by the longest elevation (as high as 3.62 Å) between the α-carbon atoms of two consecutive α-amino acids. Despite this intriguing property, however, it is only poorly investigated and understood. Here, using a complete series of C(α,α)-diethylglycine (Deg) homo-oligopeptide esters to the pentamer level, we exploited the properties of a fluorophore and a quencher, synthetically positioned at the N- and C-termini of the main chain, respectively, to check the applicability of the fully-extended conformation as a rigid molecular spacer. The fluorescence study was complemented by FT-IR absorption and NMR conformational investigations. The X-ray diffraction structures of selected compounds are also reported. Unfortunately, we find that, even in a solvent of low polarity, such as chloroform, in this peptide series an equilibrium does take place between the fragile fully-extended conformation and the 3(10)-helical structure, the latter becoming more and more stable as the main chain is elongated. Since the Deg homo-peptide esters lacking any te...Continue Reading

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Citations

Feb 3, 2015·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marco CrismaClaudio Toniolo
Aug 15, 2015·The Journal of Organic Chemistry·Yosuke DemizuMasaaki Kurihara
Jul 31, 2013·Biopolymers·Cristina PeggionClaudio Toniolo
May 6, 2020·ChemPlusChem·Kristina Vlahoviček-KahlinaIvanka Jerić
Apr 18, 2014·Chemical Communications : Chem Comm·David A ChaplinSebastian H B Kroll
May 17, 2014·Organic & Biomolecular Chemistry·Sarah J PikeJonathan Clayden
Sep 3, 2014·The Journal of Organic Chemistry·Makoto ObaMasakazu Tanaka
Nov 7, 2012·The Journal of Physical Chemistry. B·Jordi CasanovasCarlos Alemán

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