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Synthesis and C 2 ‐symmetric structure of a cyclotetrapeptide composed of anthranilic acid and leucine
Author(s) -
Akazome Motohiro,
Enzu Masashi,
Takagi Koji,
Matsumoto Shoji
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20972
Subject(s) - chemistry , hydrogen bond , anthranilic acid , chirality (physics) , crystal structure , crystallography , stereochemistry , leucine , residue (chemistry) , molecule , amino acid , organic chemistry , chiral symmetry , biochemistry , physics , quantum mechanics , nambu–jona lasinio model , quark
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. Chirality, 2011. © 2011 Wiley‐Liss, Inc.