Synthesis and C(2) -symmetric structure of a cyclotetrapeptide composed of anthranilic acid and leucine |
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| Authors: | Akazome Motohiro Enzu Masashi Takagi Koji Matsumoto Shoji |
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| Affiliation: | Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Inageku, Chiba, Japan. akazome@faculty.chiba-u.jp |
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| Abstract: | A chiral cyclotetrapeptide (1) was synthesized from 2-nitrobenzoic acid and leucine. A single-crystal X-ray of the compound revealed a C(2) -symmetric bowl-shaped structure. The cyclic compound had a unique hydrogen-bonding network composed of three-centered hydrogen bonds and bifurcated hydrogen bonds between NH and CO of anthranilic residue. The NMR spectra and molecular modeling of 1 also suggested the chiral bowl structure. |
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| Keywords: | bowl‐shaped structure coupling reagents hydrogen bond conformation X‐ray crystallographic analysis molecular mechanics |
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