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Helical l-Leu-Based Peptides Having Chiral Five-Membered Carbocyclic Ring Amino Acids with an Ethylene Acetal Moiety


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Title: Helical l-Leu-Based Peptides Having Chiral Five-Membered Carbocyclic Ring Amino Acids with an Ethylene Acetal Moiety
Authors: Koba, Yurie / Ueda, Atsushi / Oba, Makoto / Doi, Mitsunobu / Demizu, Yosuke / Kurihara, Masaaki / Tanaka, Masakazu
Issue Date: 11-Sep-2017
Publisher: Wiley-VCH Verlag GmbH & Co.
Citation: ChemistrySelect, 2(26), pp.8108-8114; 2017
Abstract: l–Leu-based heteropeptides having (R)- or (S)-chiral five-membered carbocyclic ring amino acids (Ac5c3EG) with an ethylene acetal moiety were prepared. A conformational analysis using FT-IR absorption, 1H NMR, and circular dichroism (CD) spectra revealed that l–Leu-based hexapeptides and nonapeptides having (R)- or (S)-Ac5c3EG formed right-handed (P) helical structures in solution. An X-ray crystallographic analysis of nonapeptides 5 a and 5 b showed similar right-handed (P) α-helical structures, without an intramolecular hydrogen bond of the peptide N–H⋅⋅⋅–O– (acetal) type.
Keywords: amino acids / conformation analysis / helical structures / peptides
URI: http://hdl.handle.net/10069/38332
ISSN: 23656549
DOI: 10.1002/slct.201700832
Rights: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: ChemistrySelect, 2(26), pp.8108-8114; 2017, which has been published in final form at http://dx.doi.org/10.1002/slct.201700832. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/38332

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