β-Turn analogues in model αβ-hybrid peptides: structural characterization of peptides containing β(2,2)Ac6c and β(3,3)Ac6c residues

Chemistry, an Asian Journal
Krishnayan BasuroyP Balaram

Abstract

The effect of gem-dialkyl substituents on the backbone conformations of β-amino acid residues in peptides has been investigated by using four model peptides: Boc-Xxx-β(2,2)Ac(6)c(1-aminomethylcyclohexanecarboxylic acid)-NHMe (Xxx = Leu (1), Phe (2); Boc = tert-butyloxycarbonyl) and Boc-Xxx-β(3,3)Ac(6)c(1-aminocyclohexaneacetic acid)-NHMe (Xxx = Leu (3), Phe (4)). Tetrasubstituted carbon atoms restrict the ranges of stereochemically allowed conformations about flanking single bonds. The crystal structure of Boc-Leu-β(2,2)Ac(6)c-NHMe (1) established a C(11) hydrogen-bonded turn in the αβ-hybrid sequence. The observed torsion angles (α(ϕ≈-60°, ψ≈-30°), β(ϕ≈-90°, θ≈60°, ψ≈-90°)) corresponded to a C(11) helical turn, which was a backbone-expanded analogue of the type III β turn in αα sequences. The crystal structure of the peptide Boc-Phe-β(3,3)Ac(6)c-NHMe (4) established a C(11) hydrogen-bonded turn with distinctly different backbone torsion angles (α(ϕ≈-60°, ψ≈120°), β(ϕ≈60°, θ≈60°, ψ≈-60°)), which corresponded to a backbone-expanded analogue of the type II β turn observed in αα sequences. In peptide 4, the two molecules in the asymmetric unit adopted backbone torsion angles of opposite signs. In one of the molecules, the Phe resi...Continue Reading

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Citations

Jan 16, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marta SlupskaAleksandra Misicka
Nov 22, 2014·Chemistry : a European Journal·Iván García-GonzálezJesús M Peregrina
Mar 17, 2016·Journal of Biomolecular Structure & Dynamics·Yousuf SameenaIsrael V M V Enoch
Apr 26, 2017·Chemistry : a European Journal·Naiem Ahmad WaniRajkishor Rai
May 6, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Héloise BoulletPhilippe Karoyan
Nov 13, 2012·Organic & Biomolecular Chemistry·Sophie Thétiot-LaurentValérie Alezra

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