Structural and conformational studies of [Ile7] and [Leu7]surfactins from Bacillus subtilis natto

A novel [Ile7]surfactin (1), which showed anti-human immunodeficiency virus activity, has been isolated from Bacillus subtilis natto. Structural and conformational analysis of the peptide backbone of [Ile7]surfactin was conducted by a combination of various two-dimensional (2D) nuclear magnetic resonance (NMR), circular dichroism (CD) spectroscopy and simulated annealing calculations, compared with a known [Leu7]surfactin (2). Both surfactins were shown to exist in different conformational states in both polar and apolar solvents.