Collision-induced decomposition of sphingomyelins for structural elucidation

Ann, Qinghong; Adams, Jeaneatte

doi:10.1002/bms.1200220504

Cited by 22 publications

(14 citation statements)

References 27 publications

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“…In CID, SM typically produces the charged phosphocholine head group fragment and no other significant fragments [15, 67, 68]. Here, SM provides very similar MAD and CID spectra with the phosphocholine fragment being the dominant product in both cases (Figure 5).…”

Section: Methods and Instrumentationmentioning

confidence: 86%

Radical-induced fragmentation of phospholipid cations using metastable atom-activated dissociation mass spectrometry (MAD-MS)

Deimler

Sander²,

Jackson

2015

International Journal of Mass Spectrometry

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The fragmentation pattern of several protonated 1+ phosphatidylcholines (PCs) were studied using low energy collision induced dissociation (CID) and helium metastable atom-activated dissociation (He-MAD). He-MAD of the protonated compounds produced a dominant phosphocholine head group at m/z 184 as well as typical sn-1 and sn-2 glycerol fragments such as [M+H–Rx-1CHC=O]+ and [M+H-Rx-1CO2H]+. Within the aliphatic chain, He-MAD showed fragments consistent with high-energy collision induced dissociation (HE-CID) and products/pathways consistent with Penning ionization of the 1+ precursor ions to their respective radical dications. These Penning ionization products included both singly and doubly charged radical fragments, and the fragment ions are related to the number and position of double bonds in the acyl chains. Fragments created through HE-CID-like fragmentation followed classic charge remote fragmentation pathways including ladder-like fragmentation along the acyl chain, except for additional or missing peaks due to predictable rearrangement reactions. He-MAD therefore shows utility in being able to effectively fragment singly charged lipids into a variety of useful product ions using both radical and high-energy processes in the confines of a 3D ion trap.

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Section: Methods and Instrumentationmentioning

confidence: 86%

Radical-induced fragmentation of phospholipid cations using metastable atom-activated dissociation mass spectrometry (MAD-MS)

Deimler

Sander²,

Jackson

2015

International Journal of Mass Spectrometry

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show abstract

“…The structural chemist can readily elucidate structures of ceramide derivatives, for example, glycosphingolipids (17) and sphingomyelins (18), by comparing the product ions from ceramide derivatives with those from ceramides (Ann & Adams, 1993b;Ju, Wei & Her, 1994). Low-energy CA of [M Met] ions of sphingomyelin also produces some product ions from charge-remote fragmentation.…”

Section: H Ceramides and Their Derivativesmentioning

confidence: 99%

Applications and mechanisms of charge-remote fragmentation

Cheng

Gross

2000

Mass Spectrom. Rev.

255

119

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“…The same research group also published a nomenclature for product ions of deprotonated precursor ion of (multiply) unsaturated fatty acids for the first time although previous researchers investigated the fragmentation behavior of deprotonated as well as cationized fatty acid precursor ions in detail by high-energy CID [22][23][24][25][26][27][28][29][30][31][32] which was also described in one review [33]. Later on, a product ion nomenclature for ceramides and sphingomyelins, the first one for complex lipids comprising at least of a sphingoid base and one amide-linked fatty acid, was published by Ann and Adams [34][35][36].…”

Section: Introductionmentioning

confidence: 97%