Email this article Gas-Phase Fragmentation Studies of Biotinylated, Hexaethylene Glycol–Spacered Oligosaccharides—Molecular Probes—Using Electrospray Mass Spectrometry on a Hybrid High-Resolution Mass Spectrometer
- Authors: Chizhov A.O.1, Argunov D.A.1, Gening M.L.1, Sukhova E.V.1, Khatuntseva E.A.1, Karelin A.A.1, Komarova B.S.1, Orekhova M.V.1, Krylov V.B.1, Yasunskii D.V.1, Tsvetkov Y.E.1, Nifantiev N.E.1
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Affiliations:
- Zelinsky Institute of Organic Chemistry
- Issue: Vol 72, No 13 (2017)
- Pages: 1312-1321
- Section: Articles
- URL: https://journals.rcsi.science/1061-9348/article/view/182717
- DOI: https://doi.org/10.1134/S1061934817130044
- ID: 182717
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Abstract
The electrospray ionization high-resolution mass spectra of biotinylated hexaethylene glycol–spacered molecular probes bearing biologically relevant carbohydrate moieties in positive and negative modes were recorded and interpreted. Collisionally induced decay mass spectra (positive mode) revealed different patterns depending on the charge of the parent ion, attached cations (or ions), the composition, and the sequence of carbohydrate fragments. The most intense peaks (two series) originated from the sequential cleavage of glycoside bonds resulting in charge location on the reducing end (Y series observed for all of the test compounds) or nonreducing end (B series). Hexaethylene glycol chain fragmentation giving rise to the cleavage of the C–O bond remote from the biotin moiety was observed. Other fragment ions lighter than the above by a difference of (C2H4O)n were absent or much smaller. Similar fragmentation was found for all of the nonsulfated biotinylated glycosides with the hexaethylene glycol spacer thus demonstrating that this type of fragmentation was characteristic of such molecular probes. Similar cleavages along with biotin moiety decay via the elimination of H2S and H2CS were observed for negative ions in the collisionally induced decay mass spectra of sulfated and neutral molecular probes.
About the authors
A. O. Chizhov
Zelinsky Institute of Organic Chemistry
Author for correspondence.
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
D. A. Argunov
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
M. L. Gening
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
E. V. Sukhova
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
E. A. Khatuntseva
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
A. A. Karelin
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
B. S. Komarova
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
M. V. Orekhova
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
V. B. Krylov
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
D. V. Yasunskii
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
Yu. E. Tsvetkov
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
N. E. Nifantiev
Zelinsky Institute of Organic Chemistry
Email: chizhov@ioc.ac.ru
Russian Federation, Moscow, 119991
