info:eu-repo/semantics/article
A novel synthetic approach to tyrosine dimers based on pterin photosensitization
Fecha
2017-12Registro en:
Reid, Lara Olivia; Castaño Espinal, Diana Carolina; Dantola, Maria Laura; Lhiaubet Vallet, Virginie; Miranda, Miguel A.; et al.; A novel synthetic approach to tyrosine dimers based on pterin photosensitization; Elsevier; Dyes and Pigments; 147; 12-2017; 67-74
0143-7208
CONICET Digital
CONICET
Autor
Reid, Lara Olivia
Castaño Espinal, Diana Carolina
Dantola, Maria Laura
Lhiaubet Vallet, Virginie
Miranda, Miguel A.
Luisa Marin, M.
Thomas, Andrés Héctor
Resumen
Oxidative damage to proteins leads to a variety of modifications that are markers of pathogenesis. One of the most important modifications is the dityrosine (Tyr2) cross-link, resulting from an oxidative covalent bond between two tyrosines (Tyr). An optimized methodology for preparation of pure Tyr2 is important to investigate in detail its physicochemical properties and reactivity. Pterin (Ptr), the parent and unsubstituted compound of oxidized pterins, is able to photosensitize the cross-linking of free tyrosine (Tyr) and tyrosine residues of peptides and proteins through a photoinduced electron transfer mechanism. We have optimized a simple, one-step photocatalyzed formation of Tyr2, using Ptr as photocatalyst. Our procedure is carried out in aqueous solutions under UV-A radiation for few minutes. The purification of Tyr2 is performed by reverse-phase chromatography. The obtained highly pure solution is used to fully characterize the Tyr2 (exact mass and 1H, 1H-1H COSY; DEPT; HSQC and HMBC NMR experiments) and to deeper study its fluorescence properties.