Chemical and enzymatic oxidative coupling of 5-hydroxy-N,N-dimethyltryptamine with amines.
Journal of medicinal chemistry July 1, 1987 DOI: 10.1021/jm00390a020
Summary
A remarkable fluorescent adduct was created through the oxidative coupling of serotonin derivatives with amino compounds. Specifically, bufotenine was oxidized using manganese dioxide and human ceruloplasmin, leading to a successful reaction with dansylcadaverine and dansyllysine. This process resulted in a unique fused oxazole structure, enhancing our understanding of serotoninergic receptor labeling. The findings illustrate innovative methods for manipulating serotonin derivatives, potentially paving the way for advancements in neuropharmacology and receptor studies.
Abstract
As part of a program aiming to obtain a covalent labeling of serotoninergic receptors we have studied the oxidative coupling of serotonin derivatives with amino compounds. The oxidation of bufotenine (2) by MnO2 and human ceruloplasmin followed by the Michael type addition with dansylcadaverine and dansyllysine gave a fluorescent adduct identified as fused oxazole structure 4.