H-bonding directed one-step synthesis of novel macrocyclic peptides from ε-aminoquinolinecarboxylic acid

✍ Scribed by Fei Li; Quan Gan; Lin Xue; Zhong-ming Wang; Hua Jiang

• Book ID: 104096378
• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 333 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.02.207

✦ Synopsis

Two macrocyclic peptides 1a and 1b were synthesized directly from e-aminoquinolinecarboxylic acid 2a and 2b, respectively. The preorganization of the uncyclized intermediates mediated by hydrogen bonding assisted the cyclization. The structures of 1a and 1b were characterized by 1 H and 13 C NMR spectroscopy and MALDI-TOF MS analysis. Solid state structure of 1a was investigated by single crystal X-ray studies. Their aggregation behaviors in solution were studied by both variable concentration and temperature 1 H NMR experiments.