In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine

Joseph Banoub; Paul Boullanger; Dominique Lafont; Alejandro Cohen; Anas El Aneed; Elizabeth Rowlands

doi:10.1016/j.jasms.2005.01.003

In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine

Joseph Banoub, Paul Boullanger, Dominique Lafont, Alejandro Cohen, Anas El Aneed, Elizabeth Rowlands

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

In this communication, the structural analysis of six synthetic O-Linked amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine was performed by electrospray ionization mass spectrometry in the positive ion mode, with a QqTOF-MS/MS hybrid instrument. The MS/MS analyses provided evidence for the "in situ" formation, in the collision cell of the tandem mass spectrometer, of an unexpected and unique [C-glycoside]⁺ product ion, resulting from an ion-molecule reaction between the N-acetyl-D-glucosamine oxonium ion and the neutral cholesta-3,5-diene molecule. Quasi MS³ analysis of this ion resulted in the dissociation of the precursor [C-glycoside]⁺ ion, which produced the expected third generation N-acetyl-D-glucosamine oxonium and the protonated cholesta-3,5-diene product ions.

Original language	English
Pages (from-to)	565-570
Number of pages	6
Journal	Journal of the American Society for Mass Spectrometry
Volume	16
Issue number	4
DOIs	https://doi.org/10.1016/j.jasms.2005.01.003
Publication status	Published - Apr 2005
Externally published	Yes

Bibliographical note

Funding Information:
JB acknowledges the financial support of the Natural Sciences and Engineering Research Council of Canada for a Discovery Grant, and Applied Biosystems for generously providing extra ionization sources necessary for ESI-QqTOF-MS experiments.

ASJC Scopus Subject Areas

Structural Biology
Spectroscopy

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10.1016/j.jasms.2005.01.003

Cite this

Banoub, J., Boullanger, P., Lafont, D., Cohen, A., El Aneed, A., & Rowlands, E. (2005). In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine. Journal of the American Society for Mass Spectrometry, 16(4), 565-570. https://doi.org/10.1016/j.jasms.2005.01.003

In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine. / Banoub, Joseph; Boullanger, Paul; Lafont, Dominique et al.
In: Journal of the American Society for Mass Spectrometry, Vol. 16, No. 4, 04.2005, p. 565-570.

Research output: Contribution to journal › Article › peer-review

Banoub, J, Boullanger, P, Lafont, D, Cohen, A, El Aneed, A & Rowlands, E 2005, 'In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine', Journal of the American Society for Mass Spectrometry, vol. 16, no. 4, pp. 565-570. https://doi.org/10.1016/j.jasms.2005.01.003

Banoub J, Boullanger P, Lafont D, Cohen A, El Aneed A, Rowlands E. In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine. Journal of the American Society for Mass Spectrometry. 2005 Apr;16(4):565-570. doi: 10.1016/j.jasms.2005.01.003

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abstract = "In this communication, the structural analysis of six synthetic O-Linked amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine was performed by electrospray ionization mass spectrometry in the positive ion mode, with a QqTOF-MS/MS hybrid instrument. The MS/MS analyses provided evidence for the {"}in situ{"} formation, in the collision cell of the tandem mass spectrometer, of an unexpected and unique [C-glycoside]+ product ion, resulting from an ion-molecule reaction between the N-acetyl-D-glucosamine oxonium ion and the neutral cholesta-3,5-diene molecule. Quasi MS3 analysis of this ion resulted in the dissociation of the precursor [C-glycoside]+ ion, which produced the expected third generation N-acetyl-D-glucosamine oxonium and the protonated cholesta-3,5-diene product ions.",

author = "Joseph Banoub and Paul Boullanger and Dominique Lafont and Alejandro Cohen and {El Aneed}, Anas and Elizabeth Rowlands",

note = "Funding Information: JB acknowledges the financial support of the Natural Sciences and Engineering Research Council of Canada for a Discovery Grant, and Applied Biosystems for generously providing extra ionization sources necessary for ESI-QqTOF-MS experiments.",

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AU - Cohen, Alejandro

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In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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