Total Synthesis and Antimicrobial Activity of a Natural Cycloheptapeptide of Marine Origin

Abstract

The present study deals with the first total synthesis of the proline-rich cyclopolypeptide stylisin 2 via a solution phase technique by coupling of the Boc-l-Pro-l-Ile-l-Pro-OH tripeptide unit with the l-Phe-l-Pro-l-Pro-l-Tyr-OMe tetrapeptide unit, followed by cyclization of the resulting linear heptapeptide fragment. The chemical structure of the finally synthesized peptide was elucidated by FTIR, 1H/13C-NMR and FAB MS spectral data, as well as elemental analyses. The newly synthesized peptide was subjected to antimicrobial screening against eight pathogenic microbes and found to exhibit potent antimicrobial activity against Pseudomonas aeruginosa, Klebsiella pneumoniae and Candida albicans, in addition to moderate antidermatophyte activity against pathogenic Trichophyton mentagrophytes and Microsporum audouinii when compared to standard drugs—gatifloxacin and griseofulvin.

Keywords

• marine natural product
• stylisin 2
• Stylissa caribica
• peptide synthesis
• antimicrobial activity