A new fragmentation rearrangement of the N-terminal protected amino acids using ESI-MS/MS.

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2006-12-09
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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.
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Zhu ZT, Li YM, Guo YT, Sun M, Zhao YF. A new fragmentation rearrangement of the N-terminal protected amino acids using ESI-MS/MS. Indian Journal of Biochemistry & Biophysics. 2006 Dec; 43(6): 372-6