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Conformational studies on peptides having chiral five-membered ring amino acid with two azido or triazole functional groups within the sequence of Aib residues


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Title: Conformational studies on peptides having chiral five-membered ring amino acid with two azido or triazole functional groups within the sequence of Aib residues
Authors: Oba, Makoto / Kawabe, Naomi / Takazaki, Hiroomi / Demizu, Yosuke / Doi, Mitsunobu / Kurihara, Masaaki / Suemune, Hiroshi / Tanaka, Masakazu
Issue Date: 18-Nov-2014
Publisher: Elsevier Limited
Citation: Tetrahedron, 70(46), pp.8900-8907; 2014
Abstract: The chiral cyclic α,α-disubstituted α-amino acid, (3R,4R)-1-amino-3,4-diazido-1-cyclopentanecarboxylic acid [(R,R)-Ac5cdN3], was introduced into achiral α-aminoisobutyric acid (Aib) peptides. The azido groups of (R,R)-Ac5cdN3 in the peptides were efficiently converted into 1,2,3-triazole functional groups. FTIR, 1H NMR, and CD spectra revealed that the dominant conformations of all peptides in solution were 310-helical structures without controlling the helical-screw sense. X-ray crystallographic analyses of peptides containing (R,R)-Ac5cdN3 showed that both the right-handed (P) and left-handed (M) 310-helical structures were present in the crystal state.
Keywords: Amino acids / Chirality / Conformation analysis / Helical structures Peptides
URI: http://hdl.handle.net/10069/35165
ISSN: 00404020
DOI: 10.1016/j.tet.2014.09.086
Rights: © 2014 Elsevier Ltd. / NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, 70, 46, (2014)
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/35165

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