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Production, isolation and characterization of [Leu4]- and [Ile4]surfactins from Bacillus subtilis

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Summary

Bacillus subtilis coproduces several surfactin variants that are powerful biosurfactants and have potential applications in biology and industry. A single amino acid substitution in the heptapeptide moiety of surfactins strongly modifies their properties. To better establish structure-activity relationships and to search new variants with enhanced properties, Bacillus subtilis was grown into two modified culture media. Two new variants were isolated by chromatographic methods and studied by NMR spectroscopy. As planned, modifications consisted in the substitution of the l-valine residue at the fourth position by a more hydrophobic residue, i.e., leucine or isoleucine. These [Leu4]- and [Ile4]surfactins have a higher affinity for hydrophobic solvents and a twice improved surfactant power. Structure-property correlations were confirmed by analysis of the hydrophobic residue distribution in the three-dimensional model of the structure of surfactin in solution.

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Abbreviations

DMSO:

dimethylsulfoxide

1D, 2D, 3D:

one-, two-, three-dimensional

TLC:

thin layer chromatography

CMC:

critical micellar concentration

NMR:

nuclear magnetic resonance

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Authors and Affiliations

  1. Centre de Biophysique Moléculaire (CNRS), F-45071, Orléans, France

    Jean-Marc Bonmatin, Henri Labbé, Régine Maget-Dana & Marius Ptak

  2. Université d'Orléans, F-45071, Orléans, France

    Jean-Marc Bonmatin, Henri Labbé, Régine Maget-Dana & Marius Ptak

  3. Laboratoire de Biochimie Analytique et Synthèse Bioorganique, Université Claude Bernard Lyon 1, F-69622, Villeurbanne, France

    Isabelle Grangemard & Françoise Peypoux

  4. Laboratoire de Biochimie Microbienne, Université Claude Bernard Lyon 1, F-69622, Villeurbanne, France

    Georges Michel

Authors
  1. Jean-Marc Bonmatin
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  2. Henri Labbé
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  3. Isabelle Grangemard
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  4. Françoise Peypoux
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  5. Régine Maget-Dana
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  6. Marius Ptak
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  7. Georges Michel
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Bonmatin, JM., Labbé, H., Grangemard, I. et al. Production, isolation and characterization of [Leu4]- and [Ile4]surfactins from Bacillus subtilis . Lett Pept Sci 2, 41–47 (1995). https://doi.org/10.1007/BF00122922

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  • DOI: https://doi.org/10.1007/BF00122922

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