Ultraviolet laser desorption ionisation mass spectrometry of selected calixarenes with and without matrix assistance

Linnemayr, Katharina; Allmaier, Günter

doi:10.1255/ejms.32

Cited by 9 publications

(9 citation statements)

References 1 publication

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“…Loss of alkyl groups during MALDI-TOF MS of similar calix [4]resorcinarenes has been reported previously. 9 Fragmentation complicates the determination of a quantitative molecular mass distribution. This is because to calculate the C-HPB-4-tBOC25 molecular mass moments properly the intensity of the fragment ions must be assigned to the corresponding precursor ion without regard to whether the charge resides on the main ion or the lost fragment.…”

Section: Resultsmentioning

confidence: 99%

“…This is because the desorption and/or ionization probabilities for each species may not be equal due to the presence of different numbers of functional groups. 9,10 To overcome this challenge we use a signal intensity calibration technique for polydisperse materials first used by Zhu, Yalcin and Li on mixtures of polystyrenes. 11 From the qualitative method of Zhu et al, a rigorous quantitative method was derived by Guttman et al…”

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confidence: 99%

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Quantitative measurement of the polydispersity in the extent of functionalization of glass‐forming calix[4]resorcinarenes

Wallace

Flynn

Guttman

et al. 2009

Rapid Comm Mass Spectrometry

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The polydispersity in the degree of functionalization for two calix[4]resorcinarenes was determined by measuring quantitatively their molecular mass distribution with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. A mathematical method for polydisperse materials is described that creates a calibration curve to correct the ion signal intensities in the mass spectrum to give a more reliable molecular mass distribution. Correction is required due to various sample preparation and instrumental effects that may produce a systematic mass bias in the number of oligomers measured. This method employs gravimetric mixtures of analytes with different degrees of functionalization. One calix[4]resorcinarene was found to give accurate molecular mass distributions with little correction, while another, having a very similar molecular structure, was found to exhibit strong over-counting of the oligomers having a high degree of functionalization.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Quantitative measurement of the polydispersity in the extent of functionalization of glass‐forming calix[4]resorcinarenes

Wallace

Flynn

Guttman

et al. 2009

Rapid Comm Mass Spectrometry

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“…10,11 However, in most studies MS was used only for the determination of complex stoichiometry or for the confirmation of molecular mass of newly synthesized calixarene derivatives. [12][13][14] More detailed studies on underivatized calix4arenes and those whose phenolic hydroxyl groups were partially or completely substituted with ester or ether groups were performed by MALDI MS. 15 The signal of sodiated molecular ion was dominant in all spectra. The loss of hydroxyl groups was observed for underivatized calixarenes, whereas the most abundant fragment ion in MS/MS spectrum of substituted calixarenes was assigned to the loss of side chains.…”

Section: Introductionmentioning

confidence: 88%

ESI MS/MS Study of Calix[4]arene Derivatives and their Metal Complexes

Benković¹,

Tomišić²,

Frkanec³

et al. 2012

Croat. Chem. Acta

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, Yb 3+ ) were analyzed by ESI MS. The influences of the solvent (acetonitrile, methanol, addition of formic acid or sodium acetate) and the calixarene:cation molar ratio on signal intensities were investigated. Comprehensive MS/MS analyses were performed of all singly and doubly charged ions of 1-3 and their complexes, and fragmentation pathways were proposed. An inductive cleavage was observed during dissociation of protonated ions, while the presence of alkali-metal or lanthanide cations caused homolytic cleavage and formation of radical cations. The results of MS analysis were in accordance with those obtained by other techniques (spectrophotometric, potentiometric, and conductometric titrations). The MS/MS experiments could be used as fast and sensitive method for prediction of relative stabilities of calixarene complexes with metal ions. (doi: 10.5562/cca2125)

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“…77 Gas-phase complexes of calixarenes can be ionized by a number of mass spectrometric methods. 78,79 In Fig. 4 representative calixarene structures are reported.…”

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confidence: 99%

Molecular recognition by mass spectrometry

Tullio¹,

Reale²,

Angelis³

2005

J. Mass Spectrom.

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A recent major advance in the field of mass spectrometry in the biomolecular sciences is represented by the study of the supramolecular interactions among two or more partners in the gas phase. A great deal of chemistry and most of biochemistry concerns molecular interactions taking place in solution. The electrospray technique, which allows direct sampling from solution, and soft ionization of the solute without deposition into the analyte of large amounts of energy, guarantees in many cases the survival of noncovalent bondings and, hence, the direct analysis of the supramolecular complexes present in the condensed phase. The proper preparation of the solution to be studied and also the expert and accurate setting and use of the instrumental parameters are the prerequisites for gaining results as to the specific interactions between, for instance, a protein conformationally modified by its specific metal ion, eventually, and a ligand molecule. The analysis of the charge state of the protein itself and of the modifications of the complex integrity by activating collisions are also methods for studying the biomolecule-molecule interactions. Accordingly, this new mass spectrometric approach to the supramolecular chemistry, which could be also defined as 'supramolecular mass spectrometry', allows the study of ion-protein, protein-protein, protein-ligand and DNA-drug interactions. Chiral recognition can also be performed in the gas phase, studying by electrospray mass spectrometry the fragmentation of diastereomeric complex ions. Not the least, a deep insight can also be obtained into the formation and nature of inclusion complexes like those formed with crown ethers, cyclodextrins and calixarenes as host molecules. All these topics are treated to a certain extent in this special feature article.

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Ultraviolet laser desorption ionisation mass spectrometry of selected calixarenes with and without matrix assistance

Cited by 9 publications

References 1 publication

Quantitative measurement of the polydispersity in the extent of functionalization of glass‐forming calix[4]resorcinarenes

Quantitative measurement of the polydispersity in the extent of functionalization of glass‐forming calix[4]resorcinarenes

ESI MS/MS Study of Calix[4]arene Derivatives and their Metal Complexes

Molecular recognition by mass spectrometry

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