NDLI: Dehydrogenation and dehalogenation of amines in MALDI-TOF MS investigated by isotopic labeling.

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Dehydrogenation and dehalogenation of amines in MALDI-TOF MS investigated by isotopic labeling.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Kang, Chuanqing Zhou, Yihan Du, Zhijun Bian, Zheng Wang, Jianwei Qiu, Xuepeng Gao, Lianxun Sun, Yuequan
Description	Country affiliation: China Author Affiliation: Kang C ( State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, 130022, China.)
Abstract	Secondary and tertiary amines have been reported to form [M-H](+) that correspond to dehydrogenation in matrix-assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF MS). In this investigation, we studied the dehydrogenation of amines in MALDI-TOF MS by isotopic labeling. Aliphatic amines were labeled with deuterium on the methylene of an N-benzyl group, which resulted in the formation of [M-D](+) and [M-H](+) ions by dedeuteration and dehydrogenation, respectively. This method revealed the proton that was removed. The spectra of most tertiary amines with an N-benzyl group showed high-intensity [M-D](+) and [M-H](+) ion peaks, whereas those of secondary amines showed low-intensity ion peaks. Ratios between the peak intensities of [M-D](+) and [M-H](+) greater than 1 suggested chemoselective dehydrogenation at the N-benzyl groups. The presence of an electron donor group on the N-benzyl groups enhanced the selectivity. The dehalogenation of amines with an N-(4-halobenzyl) group was also observed alongside dehydrogenation. The amino ions from dehalogenation can undergo second dehydrogenation. These results provide the first direct evidence about the position at which dehydrogenation of an amine occurs and the first example of dehalogenation of haloaromatic compounds in MALDI-TOF MS. These results should be helpful in the structural identification and elucidation of synthetic and natural molecules.
File Format	HTM / HTML
ISSN	10765174
Issue Number	12
Volume Number	48
e-ISSN	10969888
Journal	Journal of Mass Spectrometry
Language	English
Publisher	Wiley
Publisher Date	2013-12-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Spectroscopy Discipline Chemistry Techniques Amines Chemistry Spectrometry, Mass, Matrix-assisted Laser Desorption-ionization Methods Halogenation Hydrogenation Ions Isotope Labeling Protons Journal Article Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Spectroscopy Medicine

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