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  • Title: Controlling the helical screw sense of peptides with C-terminal L-valine.
    Author: Demizu Y, Yamagata N, Sato Y, Doi M, Tanaka M, Okuda H, Kurihara M.
    Journal: J Pept Sci; 2010 Mar; 16(3):153-8. PubMed ID: 20127855.
    Abstract:
    One chiral L-valine (L-Val) was inserted into the C-terminal position of achiral peptide segments constructed from alpha-aminoisobutyric acid (Aib) and alpha,beta-dehydrophenylalanine (Delta(Z)Phe) residues. The IR, (1)H NMR and CD spectra indicated that the dominant conformations of the pentapeptide Boc-Aib-DeltaPhe-(Aib)(2)-L-Val-NH-Bn (3) and the hexapeptide Boc-Aib-DeltaPhe-(Aib)(3)-L-Val-NH-Bn (4) in solution were both right-handed (P) 3(10)-helical structures. X-ray crystallographic analyses of 3 and 4 revealed that only a right-handed (P) 3(10)-helical structure was present in their crystalline states. The conformation of 4 was also studied by molecular-mechanics calculations.
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