Synthesis and diuretic activities of pseudoproline-containing analogues of the insect kinin core pentapeptide

✍ Scribed by Bo Zhang; Junbin Gong; Yinliang Yang; Shouliang Dong

• Book ID: 105360023
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 92 KB
• Volume: 17
• Category: Article
• ISSN: 1075-2617
• DOI: 10.1002/psc.1396

✦ Synopsis

Abstract

C‐2 dimethylated/unmethylated thiazolidine‐4‐carboxylic acid and C‐2 dimethylated oxazolidine‐4‐carboxylic acid were introduced into the insect kinin core pentapeptide in place of Pro^3^, yielding three new analogues. NMR analysis revealed that the peptide bond of Phe^2^‐pseudoproline (ΨPro)^3^ is practically 100% in cis conformation in the case of dimethylated pseudoproline‐containing analogues, about 50% cis for the thiazolidine‐4‐carboxylic acid analogue and about 33% cis for the parent Pro^3^ peptide. The diuretic activities are consistent with the population of cis conformation of the Phe^2^‐ΨPro^3^/Pro^3^ peptide bonds, and the results confirm a cis Phe‐Pro bond as bioactive conformation. Copyright © 2011 European Peptide Society and John Wiley & Sons, Ltd.