Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/57336

TitleN-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors
Author(s)Fernandes, Maria José G.
Gonçalves, M. Sameiro T.
Costa, Susana P. G.
KeywordsPhototriggers
Caging groups
Neurotransmitters
Serotonin
Pyrene
Photolysis
Issue date2018
PublisherElsevier
JournalDyes and Pigments
CitationM. J. G. Fernandes, M. S. T. Gonçalves, S. P. G. Costa, “N-Pyrenylmethoxycarbonyl phototriggers for the release of serotonin, tryptamine and their biosynthetic precursors”, Dyes Pigments, 2018, 151, 356-362.
Abstract(s)An evaluation of the pyrenylmethoxycarbonyl group as a photolabile protecting group for the amino function, using neuroactive amines and amino acids as models, was carried out. 1-Hydroxymethylpyrene was reacted with serotonin and tryptamine and their corresponding amino acid precursors, L-5-hydroxytrypthophan and L-trypthophan, in the presence of N,N′-carbonyldiimidazole as carbonylating agent. Photolysis studies were carried out under irradiation at different wavelengths (250, 300, 350 and 419 nm), monitored by HPLC/UV and 1H NMR, and it was found that the carbamate bond between the active molecule and the pyrenylmethyl unit cleaved readily in short irradiation times. The results obtained at 350 nm irradiation are promising for practical purposes (4–20 min).
TypeArticle
URIhttp://hdl.handle.net/1822/57336
DOI10.1016/j.dyepig.2018.01.021
ISSN0143-7208
Publisher versionhttps://www.sciencedirect.com/science/article/abs/pii/S014372081732140X
Peer-Reviewedyes
AccessRestricted access (UMinho)
Appears in Collections:CDQuim - Artigos (Papers)

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