NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A(2)

FEBS Lett. 2000 Nov 17;485(1):76-80. doi: 10.1016/s0014-5793(00)02182-7.


Plipastatins A and B are antifungal antibiotics belonging to a family of lipopeptides capable of inhibiting phospholipase A(2) (PLA(2)) and are biosynthesised under certain circumstances by Bacillus subtilis. U-(15)N plipastatins A and B were obtained from cultures of the strain NCIB 8872 on a Landy medium modified for stable-isotope labelling by the substitution of the L-glutamic acid used as the sole nitrogen source, by (15)NH(4)Cl. These two lipo-decapeptides, lactonised by esterification of the Ile10 C-terminus with the phenolic hydroxyl of Tyr3, differ only by a D-Ala (plipastatin A)/D-Val (plipastatin B) substitution at the position 6. The (1)H- and (15)N-nuclear magnetic resonance (NMR) signals of a 4:6 mixture of plipastatins A and B were unambiguously assigned and their structures in dimethylsulfoxide solution were calculated on the basis of a set of NMR-derived restraints. Plipastatins A and B are well-defined structures in solution stabilised by a type 1 beta-turn comprising residues 6-9 and several other specific hydrogen bonds. The structures afford a first molecular basis for the future studies of their biological activities both in lipidic layers or on PLA(2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Ammonium Chloride / metabolism
  • Antifungal Agents / chemistry*
  • Bacillus subtilis / metabolism*
  • Enzyme Inhibitors / chemistry*
  • Esterification
  • Fatty Acids / biosynthesis
  • Fatty Acids / chemistry*
  • Hydrogen Bonding
  • Isotope Labeling
  • Magnetic Resonance Spectroscopy*
  • Molecular Structure
  • Nitrogen Isotopes
  • Oligopeptides / biosynthesis
  • Oligopeptides / chemistry*
  • Peptides, Cyclic
  • Phospholipases A / antagonists & inhibitors*
  • Sequence Homology
  • Solutions


  • Antifungal Agents
  • Enzyme Inhibitors
  • Fatty Acids
  • Nitrogen Isotopes
  • Oligopeptides
  • Peptides, Cyclic
  • Solutions
  • plipastatin
  • Ammonium Chloride
  • Phospholipases A