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Electrospray ionization tandem mass spectrometry differentiation of N-phosphoryl-alpha-, beta- and gamma-amino acids
Qiang, Liming ; Cao, Shuxia ; Zhao, Xiaoyang ; Mao, Xiangju ; Guo, Yanchun ; Liao, Xincheng ; Zhao, Yufen
2010-05-06 ; 2010-05-06
关键词N-phosphoryl amino acids ESI-MS/MS characteristic fragment ions PEPTIDE FORMATION PROTEIN ORIGIN Physics, Atomic, Molecular & Chemical Spectroscopy
中文摘要The fragmentation patterns of N-diisopropyloxyphosphoryl-L-alpha-Ala (DIPP-L-alpha-Ala), N-diisopropyloxyphosphoryl-D-alpha-Ala (DIPP-D-alpha-Ala), N-diisopropyloxyphosphoryi-beta-Ala (DIPP-beta-Ala) and N-diisopropyloxyphosphoryl-gamma-amino butyric acid (DIPP-gamma-Aba) were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS). DIPP-D-alpha-Ala showed the same fragmentation pathways as DIPP-L-alpha-Ala. In the fragmentation of protonated DIPP-beta-Ala, the characteristic fragment ion [M+H - 2C(3)H(6) - H2O - CH2CO](+) appeared and could be used to distinguish beta-Ala from L-alpha-Ala and D-alpha-Ala through tandem mass spectra, even though they possess the same molecular weight. In the fragmentation of protonated DIPP-gamma-Aba, the break of P-N bond occurred and an interesting protonated lactam ion with five-membered ring was generated. Furthermore, in the MS3 spectrum of [M+Na - 2C(3)H(6)](+) ion of DIPP-gamma-Aba, a strong intensity of unique fragment ion, namely lactam-sodium adduct with five-membered ring, was observed, which could be considered as a mark for gamma-amino acids. The stepwise fragmentations of their [M + Na](+) ions and [M - H](-) ions showed that they all underwent a P-N to P-O bond migration through a five-membered or six-membered or even seven-membered ring transition state, respectively, which supported the great affinity of hydroxyl for phosphoryl group. (C) 2007 Elsevier B.V. All rights reserved.
语种英语 ; 英语
出版者ELSEVIER SCIENCE BV ; AMSTERDAM ; PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS
内容类型期刊论文
源URL[http://hdl.handle.net/123456789/13410]  
专题清华大学
推荐引用方式
GB/T 7714
Qiang, Liming,Cao, Shuxia,Zhao, Xiaoyang,et al. Electrospray ionization tandem mass spectrometry differentiation of N-phosphoryl-alpha-, beta- and gamma-amino acids[J],2010, 2010.
APA Qiang, Liming.,Cao, Shuxia.,Zhao, Xiaoyang.,Mao, Xiangju.,Guo, Yanchun.,...&Zhao, Yufen.(2010).Electrospray ionization tandem mass spectrometry differentiation of N-phosphoryl-alpha-, beta- and gamma-amino acids..
MLA Qiang, Liming,et al."Electrospray ionization tandem mass spectrometry differentiation of N-phosphoryl-alpha-, beta- and gamma-amino acids".(2010).
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