Abstract
Modern mass spectrometry, including electrospray and MALDI, is applied for analysis and structure elucidation of carbohydrates. Cyclic oligosaccharides isolated from different sources (bacteria and plants) have been known for decades and some of them (cyclodextrins and their derivatives) are widely used in drug design, as food additives, in the construction of nanomaterials, etc. The peculiarities of the first- and second-order mass spectra of cyclic oligosaccharides (natural, synthetic and their derivatives and modifications: cyclodextrins, cycloglucans, cyclofructans, cyclooligoglucosamines, etc.) are discussed in this minireview.
Highlights
How to correlate MS peaks intensities registered for ions in the gas phase and concentrations of non-charged molecules existing in the solution which is injected into the electrospray ionization (ESI) ion source? There are many disclaimers in literature cautioning readers to avoid the so-called “mass spectrometric fanaticism”, for example, that it was reported for CD—Trp complexation: all non-1:1 ions observed in ESI MS “are of electrostatic rather than hydrophobic nature” [24]
Note that a synthesis of the derivatives resulted in inversion of the C-2 and C-3 configurations, so the glucopyranose residue transformed into 3-amino-3-deoxyaltropyranose unit, one can believe that the change of stereochemistry had an apparently negligible effect on tandem mass spectra
The methods of activation are restricted by CID (ESI MS) and LID (MALDI MS), for example, no studies in ECD of multiply charged positive ions of cyclic CDs were carried out
Summary
Due to the presence of hydrophobic cavities in CD molecules, these macrocycles and their derivatives are capable to form host-guest inclusion complexes with many organic substances [4,5] This opens possibilities for versatile applications of CDs, for example, for drug delivery of pharmaceutical formulations [5,6], construction of nanomaterials, sugar-based surfactants and food ingredients, preparations for controlled release of fragrances and aromas ([1] and references therein). Soft ionization methods (primarily, ESI and MALDI) make possible to transfer heavy, polar molecules into the gas phase This achievement has opened a way for complementary, mass spectrometric approaches [8] for gas-phase studies of macrocycles First- and Second-Order Mass Spectra of Cyclic Oligosaccharides and Their Derivatives
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have