A liquid chromatography-mass spectrometric method for the detection of cyclic β-amino fatty acid lipopeptides

Journal of Chromatography. a
Petra UrajováPavel Hrouzek

Abstract

Bacterial lipopeptides, which contain β-amino fatty acids, are an abundant group of bacterial secondary metabolites exhibiting antifungal and/or cytotoxic properties. Here we have developed an LC-HRMS/MS method for the selective detection of β-amino fatty acid containing cyclic lipopeptides. The method was optimized using the lipopeptides iturin A and puwainaphycin F, which contain fatty acids of similar length but differ in the amino acid composition of the peptide cycle. Fragmentation energies of 10-55eV were used to obtain the amino acid composition of the peptide macrocycle. However, fragmentation energies of 90-130eV were used to obtain an intense fragment specific for the β-amino fatty acid (CnH2n+2N(+)). The method allowed the number of carbons and consequently the length of the β-amino fatty acid to be estimated. We identified 21 puwainaphycin variants differing in fatty acid chain in the crude extract of cyanobacterium Cylindrospermum alatosporum using this method. Analogously 11 iturin A variants were detected. The retention time of the lipopeptide variants showed a near perfect linear dependence (R(2)=0.9995) on the length of the fatty acid chain in linear separation gradient which simplified the detection of minor v...Continue Reading

References

Jan 1, 1977·Biochemical Society Transactions·L DelcambeG Michel
Nov 11, 1999·Proceedings of the National Academy of Sciences of the United States of America·E H DuitmanJ Vater
Jul 24, 2004·Chemistry & Biology·Jason Micklefield
Jun 1, 2005·Journal of Natural Products·Torsten NeuhofHans von Döhren
Jun 16, 2006·FEMS Microbiology Reviews·Martin Welker, Hans von Döhren
Apr 17, 2007·Journal of Natural Products·Tianying AnKathleen S Rein
Jun 11, 2010·Analytical and Bioanalytical Chemistry·J KohoutekL Bláha
May 13, 2011·Current Drug Targets·George E ChlipalaJimmy Orjala
Jul 31, 2012·Biochimica Et Biophysica Acta·Linn OftedalLars Herfindal
Apr 20, 2014·Proceedings of the National Academy of Sciences of the United States of America·Johanna VestolaKaarina Sivonen
Jun 14, 2014·Proceedings of the National Academy of Sciences of the United States of America·Hao WangKaarina Sivonen
Oct 18, 2015·Proceedings of the National Academy of Sciences of the United States of America·Tania K ShishidoKaarina Sivonen

❮ Previous
Next ❯

Citations

Dec 15, 2016·Bioanalysis·Jana ZemenováJaroslav Kuneš
Dec 7, 2018·Applied and Environmental Microbiology·Jan MarešPavel Hrouzek
Jun 20, 2021·Physiologia Plantarum·David P FewerLars Herfindal

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.