A new fragmentation rearrangement of the N-terminal protected amino acids using ESI-MS/MS.
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.
Zhu
Zhen-Tai
ZT
Department of Chemistry, The Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, PR China.
Li
Yan-Mei
YM
Guo
Yan-Ting
YT
Sun
Ming
M
Zhao
Yu-Fen
YF
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
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010446:Peptide Fragments; D010748:Phosphopeptides