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Grangemard, I ; Peypoux, F ; Wallach, J ; Das, BC ; Labbe, H ; Caille, A ; Genest, M ; Maget-Dana, R ; Ptak, M ; Bonmatin, JM

Lipopeptides with improved properties : Structure by NMR, purification by HPLC and structure-activity relationships of new isoleucyl-rich surfactins

Journal of Peptide Science 3 (2) 145-154

par Administrateur - publié le

Abstract :

The biosynthesis of bacterial isoleucyl-rich surfactins was controlled by supplementation of L-isoleucine to the culture medium. Two new variants, the [Ile4,7]- and [Ile2,4,7]surfactins, were thus produced by Bacillus subtilis and their separation was achieved by reverse-phase HPLC. Amino acids of the heptapeptide moiety were analysed by chemical methods, and the lipid moiety was identified to B-hydroxy anteiso pentadecanoic acid by combined GC/MS. Sequences were established on the basis of two-dimensional NMR data. Because conformational parameters issuing from NMR spectra suggested that the cyclic backbone fold was globally conserved in the new variants, structure-activity relationships were discussed in details on the basis of the three-dimensional model of surfactin in solution.