Synthesis and C2-symmetric structure of a cyclotetrapeptide composed of anthranilic acid and leucine

✍ Scribed by Motohiro Akazome; Masashi Enzu; Koji Takagi; Shoji Matsumoto

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 598 KB
• Volume: 23
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20972

✦ Synopsis

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. Chirality, 2011. © 2011 Wiley‐Liss, Inc.