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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| Authors: | Makoto Oba Naomi Kawabe Hiroomi Takazaki Yosuke Demizu Mitsunobu Doi Masaaki Kurihara Hiroshi Suemune Masakazu Tanaka |
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| Affiliation: | 1. Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan;2. Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan;3. Division of Organic Chemistry, National Institute of Health Sciences, Tokyo 158-8501, Japan;4. Osaka University of Pharmaceutical Sciences, Osaka 569-1094, Japan |
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| 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. |
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| Keywords: | Amino acids Chirality Conformation analysis Helical structures Peptides |
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