External chirality-triggered helicity control promoted by introducing a beta-Ala residue into the N-terminus of chiral peptides

Biomacromolecules
Yoshihito Inai, Hisatoshi Komori

Abstract

The noncovalent chiral domino effect (NCDE), defined as chiral interaction upon an N-terminus of a 3(10)-helical peptide, will provide a unique method for structural control of a peptide helix through the use of external chirality. On the other hand, the NCDE has not been considered to be effective for the helicity control of peptides strongly favoring a one-handed screw sense. We here aim to promote the NCDE on peptide helicity using two types of nonapeptides: H-beta-Ala-Delta(Z)Phe-Aib-Delta(Z)Phe-X-(Delta(Z)Phe-Aib)(2)-OCH(3) [Delta(Z)Phe = alpha,beta-didehydrophenylalanine, Aib = alpha-aminoisobutyric acid], where X as the single chirality is L-leucine (1) or L-phenylalanine (2). NMR, IR, and CD spectroscopy as well as energy calculation revealed that both peptides alone form a right-handed 3(10)-helix. The original CD amplitudes or signs in chloroform, irrespective of a strong screw-sense preference in the central chirality, responded sensitively to external chiral information. Namely added Boc-L-amino acid stabilized the original right-handed helix, while the corresponding d-isomer destabilized it or transformed it into a left-handed helix. These peptides were also shown to bind more favorably to an L-isomer from the race...Continue Reading

References

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Citations

Feb 3, 2015·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marco CrismaClaudio Toniolo
Sep 5, 2017·Chemistry : a European Journal·Ewa Rudzińska-Szostak, Łukasz Berlicki
Apr 1, 2015·Chemical Science·Bryden A F Le BaillyJonathan Clayden
May 1, 2007·The Journal of Organic Chemistry·Hisatoshi Komori, Yoshihito Inai
Mar 1, 2011·Journal of the American Chemical Society·Jordi SolàJonathan Clayden

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