13023-73-9Relevant academic research and scientific papers
Synthetic Evidence of the Amadori-Type Alkylation of Biogenic Amines by the Neurotoxic Metabolite Dopegal
J?rgensen, Steen Ingemann,Tromp, Dorette S.,Van Maarseveen, Jan H.,Vilím, Jan,Wanner, Martin J.,Zuidinga, Ed
, (2020)
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.
Synthesis of a Biochemically Important Aldehyde, 3,4-Dihydroxyphenylglycolaldehyde
Li, Shu Wen,Elliot, William H.,Burke, William J.
, p. 337 - 342 (1994)
3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL) is an important precursor of the major brain metabolites of noradrenaline, 3,4-dihydroxyphenylglycol, and 3-methoxy-4-hydroxyphenylglycol.Methods for the synthesis of DOPEGAL have been developed.The α-hydroxy an
Convenient syntheses of biogenic aldehydes, 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde
Narayanan, Jayan,Hayakawa, Yoshio,Fan, Junfa,Kirk, Kenneth L.
, p. 191 - 197 (2007/10/03)
The title compounds were prepared from a common precursor, a bis-THP-protected dihydroxyphenylacetic acid methyl ester. Key steps are the introduction of the α-hydroxyl group by Davis oxaziridine reagent and formation of the aldehydes by DIBALH ester reduction.
