Van't Hoff Institute for Molecular Sciences , University of Amsterdam , Science Park 904 , 1098 XH Amsterdam , The Netherlands.
J Org Chem. 2020 Jan 17;85(2):1202-1207. doi: 10.1021/acs.joc.9b01948. Epub 2019 Dec 30.
The neurotransmitter metabolite 3,4-dihydroxy-phenylglycolaldehyde (dopegal) damages neurons and the myocardium by protein cross-linking, resulting in conglomerations and cell death. We investigated this process on a synthetic scale, leading to the discovery of an Amadori-type rearrangement of dopegal in the reaction with several amino acids and neuropeptides. This alkylation also occurs with neurotransmitters, suggesting an influence of dopegal on neurochemical processes. The rearrangement occurs readily under physiological conditions.
神经递质代谢产物 3,4-二羟基苯乙二醇醛（dopegal）通过蛋白质交联损伤神经元和心肌，导致聚集和细胞死亡。我们在合成规模上研究了这个过程，发现 dopegal 与几种氨基酸和神经肽反应时发生了 Amadori 型重排。这种烷基化也发生在神经递质中，表明 dopegal 对神经化学过程有影响。这种重排很容易在生理条件下发生。
