Direct evidence for the ring opening of monosaccharide anions in the gas phase: photodissociation of aldohexoses and aldohexoses derived from disaccharides using variable-wavelength infrared irradiation in the carbonyl stretch region

Brown, Darin J.; Stefan, Sarah E.; Berden, Giel; Steill, Jeffrey D.; Oomens, Jos; Eyler, John R.; Bendiak, Brad

doi:10.1016/j.carres.2011.06.018

Cited by 23 publications

(22 citation statements)

References 62 publications

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“…Direct evidence of the ring opening of monosaccharide anions in the gas phase has been demonstrated by Brown et al in 2011. 66 Therefore, different Na + complexed maltotriose ions could be formed with different collision cross-sectional areas and it is not unexpected to have more than one mobility peak detected. Figures 3e and3f are the corresponding MS/MS spectra for mobility peaks 1 and 2 in Figure 3b by selecting the compounds with drift time windows of 31–31.5 ms and 32–32.5 ms on DTIMS respectively and applying the same CE (53 V) in the trap cell of the Synapt G2.…”

Section: Resultsmentioning

confidence: 99%

Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)²

Bendiak

Siems

et al. 2013

Anal. Chem.

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A high resolution ion mobility spectrometer was interfaced to a Synapt G2 high definition mass spectrometer (HDMS) to produce IMMS-IMMS analysis. The hybrid instrument contained an electro-spray ionization source, two ion gates, an ambient pressure linear ion mobility drift tube, a quadrupole mass filter, a traveling wave ion mobility spectrometer (TWIMS) and a time of flight mass spectrometer. The dual gate drift tube ion mobility spectrometer (DTIMS) could be used to acquire traditional IMS spectra, but also could selectively transfer specific mobility selected precursor ions to the Synapt G2 HDMS for mass filtration (quadrupole). The mobility and mass selected ions could then be introduced into a collision cell for fragmentation followed by mobility separation of the fragment ions with the traveling wave ion mobility spectrometer. These mobility separated fragment ions are finally mass analyzed using a time-of-flight mass spectrometer. This results in an IMMS-IMMS analysis and provides a method to evaluate the isomeric heterogeneity of precursor ions by both DTIMS and TWIMS, to acquire a mobility-selected and mass-filtered fragmentation pattern and to additionally obtain traveling wave ion mobility spectra of the corresponding product ions. This new IMMS2 instrument enables the structural diversity of carbohydrates to be studied in greater detail. The physical separation of isomeric oligosaccharide mixtures was achieved by both DTIMS and TWIMS, with DTIMS demonstrating higher resolving power (70~80) than TWIMS (30~40). Mobility selected MS/MS spectra were obtained, and TWIMS evaluation of product ions showed that isomeric forms of fragment ions existed for identical m/z values.

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Section: Resultsmentioning

confidence: 99%

Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)²

Bendiak

Siems

et al. 2013

Anal. Chem.

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“…The deprotonation process induced by O 2 –∙ is expected to occur at the most acidic site of the hexoses, presumably the anomeric ‐OH on C 1 for Glc and the ‐OH groups on C 4 for Gal, while the acidities of the ‐OH groups on C 1 , C 2 and C 4 are close for Man . The gas‐phase acidities of hexoses could also be affected due to possible ring‐opening process of their anions . Nevertheless, the negative‐ion APCI‐QTOF‐MS spectra of Man and Gal did not show significant differences.…”

Section: Resultsmentioning

confidence: 99%

“…[30,31] The gas-phase acidities of hexoses could also be affected due to possible ring-opening process of their anions. [32] Nevertheless, the negative-ion APCI-QTOF-MS spectra of Man and Gal did not show significant differences. The [M À H]ions from Man and Gal were selected as precursor ions for further MS 2 experiments.…”

Section: Differentiation Of Glc Man and Galmentioning

confidence: 91%

Differentiation of underivatized monosaccharides by atmospheric pressure chemical ionization quadrupole time‐of‐flight mass spectrometry

Zhu

Song

Bartmess

2012

Rapid Comm Mass Spectrometry

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“…Also, the rate at which the open‐chain and cyclic forms may interconvert in the gas phase could be dependent upon the energy input into the precursor ion, which differs among different disaccharide linkages. An open‐chain carbonyl form has been shown to exist in varying proportions for different monosaccharides in the gas phase using variable‐wavelength infrared photodissociation in the carbonyl stretch region . Thus, the proportions of different configurations for the glycosyl‐glycolaldehydes derived from disaccharide dissociation could depend on kinetic barriers to achieving a true thermodynamic equilibrium among configurations in the gas phase.…”

Section: Resultsmentioning

confidence: 99%

Ion mobility mass spectrometry analysis of isomeric disaccharide precursor, product and cluster ions

Bendiak

Siems

et al. 2013

Rapid Comm Mass Spectrometry

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RATIONALE Carbohydrates are highly variable in structure owing to differences in their anomeric configurations, monomer stereochemistry, inter-residue linkage positions and general branching features. The separation of carbohydrate isomers poses a great challenge for current analytical techniques. METHODS The isomeric heterogeneity of disaccharide ions and monosaccharideglycolaldehyde product ions evaluated using electrospray traveling wave ion mobility mass spectrometry (Synapt G2 high definition mass spectrometer) in both positive and negative ion modes investigation. RESULTS The separation of isomeric disaccharide ions was observed but not fully achieved based on their mobility profiles. The mobilities of isomeric product ions, the monosaccharide-glycolaldehydes, derived from different disaccharide isomers were measured. Multiple mobility peaks were observed for both monosaccharide-glycolaldehyde cations and anions, indicating that there was more than one structural configuration in the gas phase as verified by NMR in solution. More importantly, the mobility patterns for isomeric monosaccharide-glycolaldehyde product ions were different, which enabled partial characterization of their respective disaccharide ions. Abundant disaccharide cluster ions were also observed. The Results showed that a majority of isomeric cluster ions had different drift times and, moreover, more than one mobility peak was detected for a number of specific cluster ions. CONCLUSIONS It is demonstrated that ion mobility mass spectrometry is an advantageous method to assess the isomeric heterogeneity of carbohydrate compounds. It is capable of differentiating different types of carbohydrate ions having identical m/z values as well as multiple structural configurations of single compounds.

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Direct evidence for the ring opening of monosaccharide anions in the gas phase: photodissociation of aldohexoses and aldohexoses derived from disaccharides using variable-wavelength infrared irradiation in the carbonyl stretch region

Cited by 23 publications

References 62 publications

Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)²

Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)²

Differentiation of underivatized monosaccharides by atmospheric pressure chemical ionization quadrupole time‐of‐flight mass spectrometry

Ion mobility mass spectrometry analysis of isomeric disaccharide precursor, product and cluster ions

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Direct evidence for the ring opening of monosaccharide anions in the gas phase: photodissociation of aldohexoses and aldohexoses derived from disaccharides using variable-wavelength infrared irradiation in the carbonyl stretch region

Cited by 23 publications

References 62 publications

Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)2

Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)2

Differentiation of underivatized monosaccharides by atmospheric pressure chemical ionization quadrupole time‐of‐flight mass spectrometry

Ion mobility mass spectrometry analysis of isomeric disaccharide precursor, product and cluster ions

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Product

Resources

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Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)²

Carbohydrate Structure Characterization by Tandem Ion Mobility Mass Spectrometry (IMMS)²