Determination of the amino linkage of the D-Dab residue of the cyclic lipo-octapeptide occidiofungins A-D and the antifungal activity of their analogues.

Recently, the demand for new antifungal drugs has increased due to the presence of antimicrobial resistant bacteria and their side effects. Occidiofungins (Ocfs) are cyclic lipo-octapeptides that possess unusual amino acids and potent antifungal activities. However, the chemical structure of the 2,4-diamino butyric acid (Dab) residue in the backbone of Ocfs has not been clarified thus far. Therefore, we conducted a structural analysis of the tripeptides around the Dab residue in Ocfs using 1H-NMR spectroscopy. We determined that the D-Dab residue in the peptide backbone of Ocfs has an α-amino linkage. Additionally, we found that Ocf A (5) and Bk-1119 have the same chemical structure. Moreover, the analogue possessing D-αDab (13) showed potent antifungal activity against A. oryzae.