Analysis of neutral isomeric low molecular weight carbohydrates using ferrocenyl boronate derivatization and tandem electrospray mass spectrometry
✍ Scribed by Dudley Williams; Mary K. Young
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 170 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0951-4198
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✦ Synopsis
A new analytical technique for small carbohydrates utilizing the cyclic ferrocenyl boronic esters (F c Bors) of several neutral mono-and disaccharides is demonstrated. Distinction between the diastereomers of monoand disaccharides is obtained. Analysis is by tandem electrospray-mass spectrometry (ES-MS) using a modified ion-source that promotes the preformation of ions. Selection of the molecular ion produced during single-electron oxidation of the ferrocene moiety of a specific population of saccharide isomers permits a variety of collisionally induced dissociation (CID) experiments. The resultant MS 2 /MS 3 spectra reflect the ensemble of possible cyclic esters in equilibrium. An array of stable cross pyranose ring fragment ions representing sequential carbon loss as 30 u is observed. Consequently, the system provides an informationrich set of MS n spectra containing large amounts of structural information. Identification of D-glucose (D-Glc), its two commonly found epimers (D-mannose and D-galactose), and the two major L-diastereomers of 6-dideoxymonosaccharides, L-fucose (L-Fuc) and L-rhamnose (L-Rhm), are demonstrated. Selected pairs of disaccharides can be distinguished in terms of their anomeric linkage by reference to their MS 3 spectra.