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Noncovalent association phenomena of 2,5-dihydroxybenzoic acid with cyclic and linear oligosaccharides. A matrix-assisted laser desorption/ionization time-of-flight mass spectrometric and X-ray crystallographic study

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Journal of the American Society for Mass Spectrometry

Abstract

D-Glucose and 19 glucose derivatives were investigated by positive and negative ion matrix assisted laser desorption/ionization time-of-flight mass spectrometry using 2,5-dihydroxybenzoic acid (DHB) as the matrix. The set of substrates includes oligomers of amylose and cellulose, native α-, β-, and γ-cyclodextrin, and chemically modified β- and γ-cyclodextrins. These analytes were chosen to modulate molecular weight, polarity, and capability of establishing noncovalent interactions with guest molecules. In the negative-ion mode, the DHB matrix gave rise to charged multicomponent adducts of type [M + DHB − H]− (M = oligosaccharide) selectively for those analytes matching the following conditions: (i) underivatized chemical structure and (ii) number of glucose units ≥4. In the positive-ion polarity, only some amylose and cellulose derivatives and methylated β-cyclodextrins provided small amount of cationized adducts with the matrix of type [M + DHB + X]+ (X = Na or K), along with ubiquitous [M + X]+ ions. The results are discussed by taking into account analyte-matrix association phenomena, such as hydrogen bond and inclusion phenomena, as a function of the molecular structure of the analyte. The conclusions derived by mass spectrometric data are compared with the X-ray diffraction data obtained on a single crystal of the 1:1 α-cyclodextrin — DHB noncovalent adduct.

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  1. Dipartimento di Chimica del Politecnico and C.N.R.-Centro Studi sulle Sostanze Organiche Naturali, Milano, Italy

    Andrea Mele & Luciana Malpezzi

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  1. Andrea Mele
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  2. Luciana Malpezzi
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Correspondence to Andrea Mele.

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Mele, A., Malpezzi, L. Noncovalent association phenomena of 2,5-dihydroxybenzoic acid with cyclic and linear oligosaccharides. A matrix-assisted laser desorption/ionization time-of-flight mass spectrometric and X-ray crystallographic study. J Am Soc Mass Spectrom 11, 228–236 (2000). https://doi.org/10.1016/S1044-0305(99)00143-9

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  • DOI: https://doi.org/10.1016/S1044-0305(99)00143-9

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