Collisional spectroscopy approaches in the characterization of 7‐α‐ and 7‐β‐hydroxycholesterol

Favretto, Donata; Guidugli, Federico; Seraglia, Roberta; Traldi, Pietro; Ursini, Fulvio; Sevanian, Alex

doi:10.1002/rcm.1290050507

Cited by 11 publications

(6 citation statements)

References 14 publications

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“…The ERMS, where the supplementary dipolar r.f. voltage applied to end cap electrodes was varied, has been used to study the binding affinities of noncovalently associated ions and to differentiate structurally isomeric ions 17, 18, 22, 34–43. We have recently reported that one of the projections such as an energy‐resolved projection of ERMS and the parameters obtained from the projection after obtaining regression curves are useful in distinguishing structurally isomeric oligosaccharides 22.…”

Section: Resultsmentioning

confidence: 99%

“…The importance of the ERMS has been recognized and it is applied to investigate the structures of ions and noncovalently associated ions 34–43. Based on our results that ERMS can be analyzed quantitatively,22 we applied the method to a series of trisaccharides consisting of all possible combinations of anomers,33 and describe herein a quantitative analysis of CID spectra, especially energy‐resolved spectra and the relationship between an anomeric configuration and some parameters related to the dissociation energies of individual glycosidic linkages.…”

Section: Introductionmentioning

confidence: 99%

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Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

et al. 2007

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The majority of structural investigations of oligosaccharides based on mass spectrometry use naturally occurring oligosaccharides, which do not allow extracting any common feature associated with anomeric structures and linkage positions. In order to address the issue to find such characteristics possibly contained in oligosaccharide structure, a synthetic combinatorial trisaccharide library was analyzed. The trisaccharides used in the analysis consisted of L-fucose, D-galactose and D-glucose, in which individual glycosidic linkages existed in either alpha- or beta-anomers. The analysis of energy-resolved mass spectra (ERMS) and the scattered plot analysis of some parameters obtained from ERMS for a series of trisaccharides revealed that lower activation energy was required for the dissociation of alpha-glycosides of these sugars compared to those of the corresponding beta-anomers. It is suggested that this finding may be useful in structural analysis of natural oligosaccharides.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

et al. 2007

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“…Energy-resolved mass spectrometry (ERMS) has been used to investigate the structures of ions and noncovalently associated ions [31][32][33][34][35][36][37][38][39][40]. We have analyzed isomeric oligosaccharides based on ERMS and shown that (1) the primary glycosidic linkage is more stable than the secondary glycoside linkage; and (2) ␣-glyco-␣ sides are more labile than ␤-glycosides, through inves-␤ tigation of malto (␣1¡4)-, ¡ ¡ isomalto (␣1¡6)-, and cello (␤1¡4)-oligosaccharid ¡ ¡ e [26] and trisaccharide libraries with the ␣/␤-Fuc-(1 ␤ ¡6)-␣/␤-Gal-(1 ␤ ¡6)-␣/␤-Glc-octyl ␤ sequence [27].…”

Section: Erms Analysismentioning

confidence: 99%

Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry

Daikoku

Ako

Kato

et al. 2007

J. Am. Soc. Mass Spectrom.

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Glycans, a family of compounds often attached to proteins and ceramides, are diverse molecules involved in a wide range of biological functions. Their structural analysis is necessary and is often carried out at the microscale level. Methods based on mass spectrometry are therefore used, although they do not provide information regarding isomeric structures often found in glycan structures. If one finds "factors" characteristic of a certain isomer, this information can be used to elucidate an unknown oligosaccharide sequence. One potential technique is to use energy-resolved mass spectrometry (ERMS) that has been used to distinguish a pair of isomeric compounds. Thus, compounds in a combinatorial library might be effectively used for this purpose. We analyzed a set of 16 isomeric disaccharides, the structures of which consisted of all possible combinations of anomeric configurations and interglycosidic linkage positions. All of the compounds were distinguished based on ERMS where normal collision-induced dissociation could distinguish only seven compounds. Furthermore, it was shown that ␣-glycosidic linkages of fucose were more reactive than the ␣ ␤-isomers and the secondary glycosides were more reactive than the primary . The structural characteristics of oligosaccharides are quite different from those of other biopolymers such as nucleic acids and peptides. The diversity is generated from sequential combination in the latter two types of polymers, whereas anomers, ring size, linkage position, branching, and sequence are factors in the case of oligosaccharides [2]. Furthermore, the regulatory mechanisms for oligosaccharides still need to be clarified and synthesis, which is not template dependent, thus creates further molecular diversity called glycoforms. Despite the difficulties encountered in structural determination, there are reports on how glycosylation as a type of posttranslational modification (PTM) of protein affects glycoprotein secretion [3,4].

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“…In such cases, a method utilizing quadrupole ion trap mass spectrometry (QIT-MS) is effective. For this reason, QIT-MS has been used to resolve kinetic energy by obtaining a plot of the absolute abundance of precursor and product ions versus the amplitude of radio frequency (rf) applied on end cap electrodes (energy-resolved mass spectrum, ERMS). ,− Recent advances in QIT-MS equipment allowed us to obtain CID spectra at MS n . We recognized the importance of the ERMS at different stages of MS n for confirming the quantitativeness of the technique, which will be useful for the structural determination of a wide range of isomeric compounds …”

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Analysis of Energy-Resolved Mass Spectra at MSⁿ in a Pursuit To Characterize Structural Isomers of Oligosaccharides

et al. 2006

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Analyses of energy-resolved mass spectra (ERMS) of structural isomeric oligosaccharides were carried out under collision-induced dissociation conditions at different stages of MSn. Quantitative analyses of energy-resolved curves revealed that these curves can be used to distinguish anomeric configurations and such analysis can be made regardless of the stages of MSn. Furthermore, parameters obtained from the sigmoidal shaped curves obtained for ERMS were found to be used as the structural descriptors after statistical analysis. An important finding is that analyses of these descriptors depend on neither the m/z values nor the height factors.

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Collisional spectroscopy approaches in the characterization of 7‐α‐ and 7‐β‐hydroxycholesterol

Cited by 11 publications

References 14 publications

Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry

Analysis of Energy-Resolved Mass Spectra at MSⁿ in a Pursuit To Characterize Structural Isomers of Oligosaccharides

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Collisional spectroscopy approaches in the characterization of 7‐α‐ and 7‐β‐hydroxycholesterol

Cited by 11 publications

References 14 publications

Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

Anomeric information obtained from a series of synthetic trisaccharides using energy resolved mass spectra

Discrimination of 16 structural isomers of fucosyl galactoside based on energy-resolved mass spectrometry

Analysis of Energy-Resolved Mass Spectra at MSn in a Pursuit To Characterize Structural Isomers of Oligosaccharides

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Analysis of Energy-Resolved Mass Spectra at MSⁿ in a Pursuit To Characterize Structural Isomers of Oligosaccharides