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Peptide foldamers composed of six-membered ring α,α-disubstituted α-amino acids with two changeable chiral acetal moieties


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Title: Peptide foldamers composed of six-membered ring α,α-disubstituted α-amino acids with two changeable chiral acetal moieties
Authors: Tanda, Kazuhiro / Eto, Ryo / Kato, Kazuya / Oba, Makoto / Ueda, Atsushi / Suemune, Hiroshi / Doi, Mitsunobu / Demizu, Yosuke / Kurihara, Masaaki / Tanaka, Masakazu
Issue Date: 10-Jun-2015
Publisher: Elsevier Ltd
Citation: Tetrahedron, 71(23), pp.3909-3914; 2015
Abstract: Chiral cyclic α,α-disubstituted α-amino acids with four chiral centers at their acetal moieties were synthesized. An X-ray crystallographic analysis of homo-chiral tripeptide with (2R,3R)-butane-2,3-diol acetal moieties revealed that the tripeptide formed both (P) and (M) helical structures, and all peptide main-chain N(i)-H were intramolecularly hydrogen-bonded with the side-chain acetal -O- of the same amino acid residues (i). The effect of the four chiral centers in the amino acid residue on the peptide backbone helical-screw control was very weak.
Keywords: Conformation / Foldamer / Helix / Peptides / α,α-disubstituted α-amino acid
URI: http://hdl.handle.net/10069/35480
ISSN: 00404020
DOI: 10.1016/j.tet.2015.04.031
Rights: © 2015 Elsevier Ltd. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International 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/10069/35480

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