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Intramolecular transacylation: fragmentation of protonated molecules via ion-neutral complexes in mass spectrometry.
Rapid Commun Mass Spectrom. 2009 Jul; 23(13):1970-6.RC

Abstract

An intramolecular transacylation reaction was observed in the mass spectrometry of molecules containing both benzoyl and carboxymethyl groups on an aromatic heterocyclic core. The reaction is triggered by a dissociative protonation on the heterocyclic ring at the atom (carbon or nitrogen) that bonds to the benzoyl group, leading to an intermediate ion-neutral complex. The incipient benzoyl cation in the complex migrates to attack the carboxyl group of the neutral partner at the carbonyl or hydroxyl oxygen under thermodynamic or kinetic control, respectively. Elimination of benzoic acid followed by loss of carbon monoxide takes place as a result of the transacylation.

Authors+Show Affiliations

Drug Metabolism and Pharmacokinetics, Genelabs Technologies, Inc., 505 Penobscot Drive, Redwood City, CA 94063, USA. Yaping.5.Tu@gsk.comNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Evaluation Study
Journal Article

Language

eng

PubMed ID

19504483

Citation

Tu, Ya-Ping, et al. "Intramolecular Transacylation: Fragmentation of Protonated Molecules Via Ion-neutral Complexes in Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 23, no. 13, 2009, pp. 1970-6.
Tu YP, Huang Y, Atsriku C, et al. Intramolecular transacylation: fragmentation of protonated molecules via ion-neutral complexes in mass spectrometry. Rapid Commun Mass Spectrom. 2009;23(13):1970-6.
Tu, Y. P., Huang, Y., Atsriku, C., You, Y., & Cunniff, J. (2009). Intramolecular transacylation: fragmentation of protonated molecules via ion-neutral complexes in mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 23(13), 1970-6. https://doi.org/10.1002/rcm.4108
Tu YP, et al. Intramolecular Transacylation: Fragmentation of Protonated Molecules Via Ion-neutral Complexes in Mass Spectrometry. Rapid Commun Mass Spectrom. 2009;23(13):1970-6. PubMed PMID: 19504483.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Intramolecular transacylation: fragmentation of protonated molecules via ion-neutral complexes in mass spectrometry. AU - Tu,Ya-Ping, AU - Huang,Yingying, AU - Atsriku,Christian, AU - You,You, AU - Cunniff,Jack, PY - 2009/6/9/entrez PY - 2009/6/9/pubmed PY - 2009/8/14/medline SP - 1970 EP - 6 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 23 IS - 13 N2 - An intramolecular transacylation reaction was observed in the mass spectrometry of molecules containing both benzoyl and carboxymethyl groups on an aromatic heterocyclic core. The reaction is triggered by a dissociative protonation on the heterocyclic ring at the atom (carbon or nitrogen) that bonds to the benzoyl group, leading to an intermediate ion-neutral complex. The incipient benzoyl cation in the complex migrates to attack the carboxyl group of the neutral partner at the carbonyl or hydroxyl oxygen under thermodynamic or kinetic control, respectively. Elimination of benzoic acid followed by loss of carbon monoxide takes place as a result of the transacylation. SN - 1097-0231 UR - https://www.unboundmedicine.com/medline/citation/19504483/Intramolecular_transacylation:_fragmentation_of_protonated_molecules_via_ion_neutral_complexes_in_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.4108 DB - PRIME DP - Unbound Medicine ER -