Origin and characterization of cyclodepsipeptides: Comprehensive structural approaches with focus on mass spectrometry analysis of alkali‐cationized molecular species
Résumé
Abstract Cyclodepsipeptides (CDPs) represent a huge family of chemically and structurally diverse molecules with a wide ability for molecular interactions. CDPs are cyclic peptide‐related natural products made up of both proteinogenic and nonproteinogenic amino acids linked by amide and ester bonds. The combined use of different analytical methods is required to accurately determine their integral structures including stereochemistry, thus allowing deeper insights into their often‐intriguing bioactivities and their possible usefulness. Our goal is to present the various methods developed to accurately characterize CDPs. Presently, Marfey's method and NMR (nuclear magnetic resonance) are still considered the best for characterizing CDP configuration. Nevertheless, electrospray‐high resolution tandem mass spectrometry (ESI‐HRMS/MS) is of great value for efficiently resolving CDP's composition and sequences. For instance, recent data shows that the fragmentation of cationized CDPs (e.g., [M + Li] + and [M + Na] + ) leads to selective cleavage of ester bonds and specific cationized product ions ( b series) useful to get unprecedented sequence information. Thus, after a brief presentation of their structure, biological functions, and biosynthesis, we also provide a historic overview of these various analytical approaches as well as their advantages and limitations with a special emphasis on the emergence of methods based on HRMS/MS through recent fundamental works and applications.
Mots clés
amino acid
atmospheric pressure chemical ionization
atmospheric pressure ionization
quadrupole instrument
covalent bond cleavage
cyclodepsipeptide
chemical ionization
collision induced dissociation
charge solvated
desorption chemical ionization
desorption electrospray ionization
electron ionization
electron induced dissociation
energy resolved mass spectrometry
fast atom bombardment
gas chromatography
infrared laser desorption
liquid chromatography
liquid-liquid extraction
lowmass cut-off
metastable atom-activated dissociations
matrix assisted laser desorption ionization
multiple reaction monitoring
tandem mass spectrometry
mass spectrometry
nuclear magnetic resonance
non-ribosomal peptides synthesases
surface induced dissociation
stable isotope dilution analysis
secondary ion mass spectrometry
solid phase extraction
total ion current
time of flight
MS/MS
linear ion trap
limit of detection
QUECHERS
alkali-cationized molecule
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