A novel synthetic approach to tyrosine dimers based on pterin photosensitization

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 Tyr...

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Detalles Bibliográficos
Autores principales: Reid, Lara Olivia, Castaño, Carolina, Dántola, María Laura, Lhiaubet-Vallet, Virginie, Miranda, Miguel A., Marin, M. Luisa, Thomas, Andrés Héctor
Formato: Articulo Preprint
Lenguaje:Inglés
Publicado: 2017
Materias:
Química
Dityrosine
Oxidation
Cross-linking
Pterin
Photocatalyzed synthesis
Photoinduced electron transfer
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/128209
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-128209
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Dityrosine
Oxidation
Cross-linking
Pterin
Photocatalyzed synthesis
Photoinduced electron transfer
spellingShingle Química
Dityrosine
Oxidation
Cross-linking
Pterin
Photocatalyzed synthesis
Photoinduced electron transfer
Reid, Lara Olivia
Castaño, Carolina
Dántola, María Laura
Lhiaubet-Vallet, Virginie
Miranda, Miguel A.
Marin, M. Luisa
Thomas, Andrés Héctor
A novel synthetic approach to tyrosine dimers based on pterin photosensitization
topic_facet Química
Dityrosine
Oxidation
Cross-linking
Pterin
Photocatalyzed synthesis
Photoinduced electron transfer
description 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.
format Articulo
Preprint
author Reid, Lara Olivia
Castaño, Carolina
Dántola, María Laura
Lhiaubet-Vallet, Virginie
Miranda, Miguel A.
Marin, M. Luisa
Thomas, Andrés Héctor
author_facet Reid, Lara Olivia
Castaño, Carolina
Dántola, María Laura
Lhiaubet-Vallet, Virginie
Miranda, Miguel A.
Marin, M. Luisa
Thomas, Andrés Héctor
author_sort Reid, Lara Olivia
title A novel synthetic approach to tyrosine dimers based on pterin photosensitization
title_short A novel synthetic approach to tyrosine dimers based on pterin photosensitization
title_full A novel synthetic approach to tyrosine dimers based on pterin photosensitization
title_fullStr A novel synthetic approach to tyrosine dimers based on pterin photosensitization
title_full_unstemmed A novel synthetic approach to tyrosine dimers based on pterin photosensitization
title_sort novel synthetic approach to tyrosine dimers based on pterin photosensitization
publishDate 2017
url http://sedici.unlp.edu.ar/handle/10915/128209
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