Synthesis and  C  2 ‐symmetric structure of a cyclotetrapeptide composed of anthranilic acid and leucine | Zendy

Akazome Motohiro | Zendy; Enzu Masashi | Zendy; Takagi Koji | Zendy; Matsumoto Shoji | Zendy

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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.

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