Hydroxyl transfer versus cyclization reaction in the gas phase: Sequential loss of NH₃ and CH₂CO from protonated phenylalanine derivatives.

ABSTRACT: Collisional activation of protonated phenylalanine derivatives deamination products leads to hydroxyl skeletal rearrangement versus cyclization reaction, and to form hydroxylbenzyl cation via elimination of CH₂CO. To better clarify this unusual fragmentation reaction, accurate mass measurements experiments, native isotope experiments, multiple-stage mass spectrometry experiments, different substituents experiments, and density functional theory (DFT) calculations were carried out to investigate the dissociation mechanistic pathways of protonated phenylalanine derivatives deamination products. In route 1, a three-membered ring-opening reaction and a 1,3-hydroxyl transfer (from the carbonyl carbon atom to the interposition carbon atom of carbonyl) occurs to form 3-hy

SUBMITTER: Zheng M 

PROVIDER: S-EPMC9868239 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature