Characterisation of the tyrocidine and gramicidin fractions of the TYROTHRICIN (cas 1404-88-2) complex from Bacillus brevis using liquid chromatography and mass spectrometry☆

Add time:09/07/2019    Source:sciencedirect.com

The TYROTHRICIN (cas 1404-88-2) peptide complex, isolated from the fermentation broth of Bacillus brevis, is comprised of a basic fraction of cyclic decapeptides (the tyrocidines) and a neutral fraction composed of linear peptides (the gramicidins). Previously, five cyclic compounds (tyrocidines A–E) had been characterised by classical chemical procedures, and an additional five by M. Barber, D.J. Bell, M.R. Morris, L.W. Tetler, J.J. Monaghan, W.E. Morden, B.W. Bycroft and B.N. Green, Int. J. Mass Spectrom. Ion Processes, 122 (1992) 143-150, who employed tandem mass spectrometric analysis of the crude mixture, together with an interpretative strategy based upon mass shifts related to simple amino acid substitutions. In the present work, initial profiling of the tyrothricin complex, using reverse phase liquid chromatography (HPLC) coupled directly to tandem mass spectrometry via an ionspray interface, showed that the mixture is extremely complex. Semi-preparative HPLC provided 32 fractions, some of which were still mixtures, amenable to analysis by tandem mass spectrometry using the doubly-protonated peptide precursors produced by ionspray ionisation. In this way the 10 previously known tyrocidines were confirmed, and structures of an additional 18 cyclic variants established with only minor uncertainties (e.g. present techniques could not distinguish Ile from Leu). Six linear gramicidins were known previously, and were confirmed in the present work. In addition, three previously unknown variants, of the Val1 -gramicidins A,B and C, were discovered, in which the ethanolamide residue at the C-terminus is replaced by a propanolamide residue.

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