title: A new fragmentation rearrangement of the N-terminal protected amino acids using ESI-MS/MS.
abstract: A novel fragmentation rearrangement reaction with a carboxyl oxygen negative charge migration was observed in the N-terminal protected amino acids including Fmoc-protected phosphoserine. phosphothroenine, and phosphotyrosine and their analogues using the electrospray ionization tandem mass spectrometry (ESI-MS/MS). The possible mechanism of a five-membered ring transition state was proposed and supported by the further experiments. It was found that the tendency of the rearrangement was determined by the blocking status of its C-terminal and the reaction was proved to be independent of the N-terminal and side-chain protecting groups of the amino acids.
authors.affiliation: Department of Chemistry, The Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, PR China.
authors.forename: Zhen-Tai
authors.initials: ZT
authors.lastname: Zhu
authors.forename: Yan-Mei
authors.initials: YM
authors.lastname: Li
authors.forename: Yan-Ting
authors.initials: YT
authors.lastname: Guo
authors.forename: Ming
authors.initials: M
authors.lastname: Sun
authors.forename: Yu-Fen
authors.initials: YF
authors.lastname: Zhao
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism; D005449:Fluorenes / Q000737:chemistry; D010446:Peptide Fragments / Q000737:chemistry* / Q000378:metabolism; D010748:Phosphopeptides / Q000737:chemistry* / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010446:Peptide Fragments; D010748:Phosphopeptides