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Helical structures of homo-chiral isotope-labeled α-aminoisobutyric acid peptides

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Title: Helical structures of homo-chiral isotope-labeled α-aminoisobutyric acid peptides
Authors: Ueda, Atsushi / Oba, Makoto / Izumi, Yuki / Sueyoshi, Yasuhito / Doi, Mitsunobu / Demizu, Yosuke / Kurihara, Masaaki / Tanaka, Masakazu
Issue Date: 29-Sep-2016
Publisher: Elsevier Ltd
Citation: Tetrahedron, 72(39), pp.5864-5871; 2016
Abstract: The chiral deuterium- and 13C-isotope-labeled α-aminoisobutyric acids CD3-Aib and 13CH3-Aib were enantioselectively synthesized from L-Ala aldimine using simplified Maruoka chiral phase-transfer catalysts. Homo-chiral (S)-CD3-Aib homopeptides, up to decamers, were prepared. A (R)-CD3-Aib polymer and (S)-13CH3-Aib polymer were also prepared. Conformational studies on homopeptides using CD spectra and an X-ray crystallographic analysis revealed that the preferred conformations were 310-helical structures comprising equal amounts of right-handed (P) and left-handed (M) helical-screw structures. The α-carbon chiral centers induced by the D- or 13C-isotope substitution of Aib were incapable of controlling the helical-screw directions of their oligopeptides and short polymers.
Keywords: Aib / Conformation / Helix / Peptide / α,α-Disubstituted α-amino acid
URI: http://hdl.handle.net/10069/37238
ISSN: 00404020
DOI: 10.1016/j.tet.2016.08.011
Rights: © 2016 Elsevier Ltd. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/37238

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