Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies on the β-Turn of Peptides. VIII. β-Turn Preferences of N-Acetyltetrapeptide Methylamides Related to the β-Turn Part of Gramicidin S
Kazuki SatoTsutomu HigashijimaRika SugawaraUkon Nagai
Author information

1983 Volume 56 Issue 12 Pages 3699-3702


N-Acetyl-L-Leu–X–L-Pro–L-Val methylamides (IIa: X=D-Ala, IIb: X=Gly, IIc: X=L-Ala) were synthesized and subjected to CD and 1H NMR measurements to study the β-turn preferences of these peptides. Temperature dependences of L-Val4–NH proton chemical shifts in CD3OH solution were in the order of IIa<IIb<IIc, suggesting that the populations of the β-turn conformer with 4→1 hydrogen bonding were in the order of IIa>IIb>IIc. This order of β-turn preferences coincides with the order of the magnitudes of the Cotton effects in the CD spectra of the chromophoric derivatives, N-(2,4-dinitrophenyl)tetrapeptide p-nitroanilides, having the same sequences. This agreement supports the validity of the chiroptical method to study turn tendency of tetrapeptide sequences using chromophoric derivatives reported previously.

Information related to the author

This article cannot obtain the latest cited-by information.

© The Chemical Society of Japan
Previous article Next article