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NMR structure of antibiotics plipastatins A and B from Bacillus subtilis inhibitors of phospholipase A2

L. Volpon,F. Besson,J. Lancelin

Published 2000 in FEBS Letters

ABSTRACT

Plipastatins A and B are antifungal antibiotics belonging to a family of lipopeptides capable of inhibiting phospholipase A2 (PLA2) and are biosynthesised under certain circumstances by Bacillus subtilis. U‐15N 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 15NH4Cl. 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 1H‐ and 15N‐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 β‐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 PLA2.

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