Collision-Induced Dissociation Mass Spectrometry: A Powerful Tool for Natural Product Structure Elucidation

Johnson, Andrew R.; Carlson, Erin E.

doi:10.1021/acs.analchem.5b01543

Cited by 99 publications

(70 citation statements)

References 102 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The characteristic c n ions and their formation pathways presented in this work will surely enrich the mass spectrum interpretation protocols and be of benefit to the critically evaluation of key results from protein identification by de novo sequencing. Furthermore, the proposed mechanism is not only in accordance with the previous findings on such amide compounds but also compliments findings with countless other natural products having similar structural characteristics . When compared with the charge‐directed fragmentation reactions, less attention is paid to charge‐remote pathways.…”

Section: Resultsmentioning

confidence: 99%

Investigation of c ions formed by N‐terminally charged peptides upon collision‐induced dissociation

et al. 2016

View full text Add to dashboard Cite

Peptide fragments such as b and y sequence ions generated upon low-energy collision-induced dissociation have been routinely used for tandem mass spectrometry (MS/MS)-based peptide/protein identification. The underlying formation mechanisms have been studied extensively and described within the literature. As a result, the 'mobile proton model' and 'pathways in competition model' have been built to interpret a majority of peptide fragmentation behavior. However, unusual peptide fragments which involve unfamiliar fragmentation pathways or various rearrangement reactions occasionally appear in MS/MS spectra, resulting in confused MS/MS interpretations. In this work, a series of unfamiliar c ions are detected in MS/MS spectra of the model peptides having an N-terminal Arg or deuterohemin group upon low-energy collision-induced dissociation process. Both the protonated Arg and deuterohemin group play an important role in retention of a positive charge at the N-terminus that is remote from the cleavage sites. According to previous reports and our studies involving amino acid substitutions and hydrogen-deuterium exchange, we propose a McLafferty-type rearrangement via charge-remote fragmentation as the potential mechanism to explain the formation of c ions from precursor peptide ions or unconventional b ions. Density functional theory calculations are also employed in order to elucidate the proposed fragmentation mechanisms. Copyright © 2016 John Wiley & Sons, Ltd.

show abstract

Section: Resultsmentioning

confidence: 99%

Investigation of c ions formed by N‐terminally charged peptides upon collision‐induced dissociation

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Various ion activation modes exist in tandem mass spectrometry. Nevertheless, collision‐induced dissociation (CID), including higher energy collisional dissociation (HCD, in orbitrap instruments) is by far the most widespread technique for the analysis of small molecules . Therefore, this ion activation/fragmentation technique will be used in the examples discussed in this review.…”

Section: Introductionmentioning

confidence: 99%

A tutorial in small molecule identification via electrospray ionization‐mass spectrometry: The practical art of structural elucidation

Vijlder

Valkenborg

Lemière

et al. 2017

Mass Spectrometry Reviews

185

134

View full text Add to dashboard Cite

The identification of unknown molecules has been one of the cornerstone applications of mass spectrometry for decades. This tutorial reviews the basics of the interpretation of electrospray ionization‐based MS and MS/MS spectra in order to identify small‐molecule analytes (typically below 2000 Da). Most of what is discussed in this tutorial also applies to other atmospheric pressure ionization methods like atmospheric pressure chemical/photoionization. We focus primarily on the fundamental steps of MS‐based structural elucidation of individual unknown compounds, rather than describing strategies for large‐scale identification in complex samples. We critically discuss topics like the detection of protonated and deprotonated ions ([M + H]+ and [M − H]−) as well as other adduct ions, the determination of the molecular formula, and provide some basic rules on the interpretation of product ion spectra. Our tutorial focuses primarily on the fundamental steps of MS‐based structural elucidation of individual unknown compounds (eg, contaminants in chemical production, pharmacological alteration of drugs), rather than describing strategies for large‐scale identification in complex samples. This tutorial also discusses strategies to obtain useful orthogonal information (UV/Vis, H/D exchange, chemical derivatization, etc) and offers an overview of the different informatics tools and approaches that can be used for structural elucidation of small molecules. It is primarily intended for beginning mass spectrometrists and researchers from other mass spectrometry sub‐disciplines that want to get acquainted with structural elucidation are interested in some practical tips and tricks.

show abstract

“…Fragments are formed from these slow‐heating techniques via the lowest energy dissociation pathways. The application of the vibrational excitation‐based ion activation methods in the structural elucidation of NPs has been widely studied and was reviewed previously …”

Section: Introductionmentioning

confidence: 99%

Electron‐ion reaction‐based dissociation: A powerful ion activation method for the elucidation of natural product structures

Chen

Wang

Wong

et al. 2018

Mass Spectrometry Reviews

View full text Add to dashboard Cite

The structural elucidation of natural products (NPs) remains a challenge due to their structurally diversities and unpredictable functionalities, motifs, and scaffolds. Tandem mass spectrometry (MS/MS) is an effective method that assists the full elucidation of complicated NP structures. Ion activation methods play a key role in determining the fragmentation pathways and the structural information obtained from MS/MS. Electron-ion reaction-based dissociation (ExD) methods, including electron capture dissociation (ECD), electron transfer dissociation (ETD), electron-induced dissociation (EID), and electron detachment dissociation (EDD), can induce the breakage of specific chemical bonds and the generation of distinct fragment ions. This review article provides an overview of the mechanisms, instrumentation, and typical applications related to ExD MS/MS in the structural elucidation of NPs, primarly including lipids, oligosaccharides, glycoconjugates, metabolites, and pharmaceutical drugs. This work aims to reveal the capacity and potential of ExD mass spectrometry in analyzing NPs and consequently helping the NP communities to utilize the modern capabilities of MS/MS in the discovery and evaluation of novel NPs.

show abstract

Collision-Induced Dissociation Mass Spectrometry: A Powerful Tool for Natural Product Structure Elucidation

Cited by 99 publications

References 102 publications

Investigation of c ions formed by N‐terminally charged peptides upon collision‐induced dissociation

Investigation of c ions formed by N‐terminally charged peptides upon collision‐induced dissociation

A tutorial in small molecule identification via electrospray ionization‐mass spectrometry: The practical art of structural elucidation

Electron‐ion reaction‐based dissociation: A powerful ion activation method for the elucidation of natural product structures

Contact Info

Product

Resources

About