Determination of Branched β-Cyclodextrin–Prostaglandin Complexes Using Electrospray Ionization Mass Spectrometry

Yamane, Naoe; Tozuka, Zenzaburo; Okada, Yasuyo; Honda, Chie; Nishi, Yuki; Tanimoto, Toshiko

doi:10.1271/bbb.80233

Cited by 3 publications

(1 citation statement)

References 33 publications

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“…Electrospray ionization mass spectrometry (ESI–MS) has been intensively applied as a rapid and powerful analytical tool to screen for host–guest complexes. − However, the specific mass-to-charge ratios ( m / z ) of the detected species may serve to quickly determine their stoichiometries , but these observations alone do not provide any structural information. Compared with the generally accepted conceptions regarding CD complexation in solution, the nature of such host–guest complexes in the gas phase remains ambiguous or even controversial.…”

Section: Introductionmentioning

confidence: 99%

Intrinsic Properties of α-Cyclodextrin Complexes with Benzoate Derivatives in the Gas Phase: An Experimental and Theoretical Study

Couzijn

Zhang

2012

J. Phys. Chem. B

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The noncovalent interactions in host-guest complexes of α-cyclodextrin (α-CD) with a series of benzoic acid derivatives (RBA) were investigated by electrospray ionization tandem mass spectrometry and density functional theory (DFT) calculations. The 1:1 stoichiometry of the anionic host-guest complexes was unequivocally confirmed by their mass-to-charge ratios (m/z) and isotope patterns. Collision-induced dissociation experiments revealed exclusive fragmentation into [α-CD](-) and neutral RBA and afforded the gas-phase kinetic stability trend [α-CD·3,5-diMeBA](-) < [α-CD·3-MeBA](-) < [α-CD·BA](-) < [α-CD·3-OHBA](-) < [α-CD·3,5-diOHBA](-). This trend follows that of the gas-phase basicities of the guest anions used, indicating that host-guest pairs with more comparable basicities form more stable complexes. DFT calculations at the M06-L/6-31+G(d,p) level of theory provided detailed structural assignments and further elucidated the experimental observations, suggesting that the anionic [α-CD·RBA](-) inclusion complexes are favored over the nonspecific complexes in the gas phase and that hydrogen bonding constitutes the primary host-guest interaction. Additionally, the results provide an estimated gas-phase basicity ΔG(0) = 325-327 kcal mol(-1) for [α-CD](-).

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Section: Introductionmentioning

confidence: 99%

Intrinsic Properties of α-Cyclodextrin Complexes with Benzoate Derivatives in the Gas Phase: An Experimental and Theoretical Study

Couzijn

Zhang

2012

J. Phys. Chem. B

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Current literature in mass spectrometry

2009

J. Mass Spectrom.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Determination of Branched β-Cyclodextrin–Prostaglandin Complexes Using Electrospray Ionization Mass Spectrometry

Cited by 3 publications

References 33 publications

Intrinsic Properties of α-Cyclodextrin Complexes with Benzoate Derivatives in the Gas Phase: An Experimental and Theoretical Study

Intrinsic Properties of α-Cyclodextrin Complexes with Benzoate Derivatives in the Gas Phase: An Experimental and Theoretical Study

Current literature in mass spectrometry

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

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