Mechanism of photooxidation of folic acid sensitized by unconjugated pterins
- Autores
- Dántola, María Laura; Denofrio, María Paula; Zurbano, Beatriz N.; Giménez, Carlos Sebastián; Ogilby, Peter R.; Lorente, Carolina; Thomas, Andrés Héctor
- Año de publicación
- 2010
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Folic acid, or pteroyl-L-glutamic acid (PteGlu), is a precursor of coenzymes involved in the metabolism of nucleotides and amino acids. PteGlu is composed of three moieties: a 6-methylpterin (Mep) residue, a p-aminobenzoic acid (PABA) residue, and a glutamic acid (Glu) residue. Accumulated evidence indicates that photolysis of PteGlu leads to increased risk of several pathologies. Thus, a study of PteGlu photodegradation can have significant ramifications. When an air-equilibrated aqueous solution of PteGlu is exposed to UV-A radiation, the rate of the degradation increases with irradiation time. The mechanism involved in this “auto-photo-catalytic” effect was investigated in aqueous solutions using a variety of tools. Whereas PteGlu is photostable under anaerobic conditions, it is converted into 6-formylpterin (Fop) and p-aminobenzoyl-L-glutamic acid (PABA-Glu) in the presence of oxygen. As the reaction proceeds and enough Fop accumulates in the solution, a photosensitized electron-transfer process starts, where Fop photoinduces the oxidation of PteGlu to Fop, and H₂O₂ is formed. This process also takes place with other pterins as photosensitizers. The results are discussed with the context of previous mechanisms for processes photosensitized by pterins, and their biological implications are evaluated.
Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas - Materia
-
Ciencias Exactas
Química
folic acid
photooxidation
pterins - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- http://creativecommons.org/licenses/by/4.0/
- Repositorio
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/144468
Ver los metadatos del registro completo
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Mechanism of photooxidation of folic acid sensitized by unconjugated pterinsDántola, María LauraDenofrio, María PaulaZurbano, Beatriz N.Giménez, Carlos SebastiánOgilby, Peter R.Lorente, CarolinaThomas, Andrés HéctorCiencias ExactasQuímicafolic acidphotooxidationpterinsFolic acid, or pteroyl-L-glutamic acid (PteGlu), is a precursor of coenzymes involved in the metabolism of nucleotides and amino acids. PteGlu is composed of three moieties: a 6-methylpterin (Mep) residue, a p-aminobenzoic acid (PABA) residue, and a glutamic acid (Glu) residue. Accumulated evidence indicates that photolysis of PteGlu leads to increased risk of several pathologies. Thus, a study of PteGlu photodegradation can have significant ramifications. When an air-equilibrated aqueous solution of PteGlu is exposed to UV-A radiation, the rate of the degradation increases with irradiation time. The mechanism involved in this “auto-photo-catalytic” effect was investigated in aqueous solutions using a variety of tools. Whereas PteGlu is photostable under anaerobic conditions, it is converted into 6-formylpterin (Fop) and p-aminobenzoyl-L-glutamic acid (PABA-Glu) in the presence of oxygen. As the reaction proceeds and enough Fop accumulates in the solution, a photosensitized electron-transfer process starts, where Fop photoinduces the oxidation of PteGlu to Fop, and H₂O₂ is formed. This process also takes place with other pterins as photosensitizers. The results are discussed with the context of previous mechanisms for processes photosensitized by pterins, and their biological implications are evaluated.Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas2010-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf1604-1612http://sedici.unlp.edu.ar/handle/10915/144468enginfo:eu-repo/semantics/altIdentifier/issn/1474-9092info:eu-repo/semantics/altIdentifier/issn/1474-905Xinfo:eu-repo/semantics/altIdentifier/doi/10.1039/c0pp00210kinfo:eu-repo/semantics/altIdentifier/pmid/20922252info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-03T11:04:24Zoai:sedici.unlp.edu.ar:10915/144468Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-03 11:04:24.489SEDICI (UNLP) - Universidad Nacional de La Platafalse |
dc.title.none.fl_str_mv |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins |
title |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins |
spellingShingle |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins Dántola, María Laura Ciencias Exactas Química folic acid photooxidation pterins |
title_short |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins |
title_full |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins |
title_fullStr |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins |
title_full_unstemmed |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins |
title_sort |
Mechanism of photooxidation of folic acid sensitized by unconjugated pterins |
dc.creator.none.fl_str_mv |
Dántola, María Laura Denofrio, María Paula Zurbano, Beatriz N. Giménez, Carlos Sebastián Ogilby, Peter R. Lorente, Carolina Thomas, Andrés Héctor |
author |
Dántola, María Laura |
author_facet |
Dántola, María Laura Denofrio, María Paula Zurbano, Beatriz N. Giménez, Carlos Sebastián Ogilby, Peter R. Lorente, Carolina Thomas, Andrés Héctor |
author_role |
author |
author2 |
Denofrio, María Paula Zurbano, Beatriz N. Giménez, Carlos Sebastián Ogilby, Peter R. Lorente, Carolina Thomas, Andrés Héctor |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
Ciencias Exactas Química folic acid photooxidation pterins |
topic |
Ciencias Exactas Química folic acid photooxidation pterins |
dc.description.none.fl_txt_mv |
Folic acid, or pteroyl-L-glutamic acid (PteGlu), is a precursor of coenzymes involved in the metabolism of nucleotides and amino acids. PteGlu is composed of three moieties: a 6-methylpterin (Mep) residue, a p-aminobenzoic acid (PABA) residue, and a glutamic acid (Glu) residue. Accumulated evidence indicates that photolysis of PteGlu leads to increased risk of several pathologies. Thus, a study of PteGlu photodegradation can have significant ramifications. When an air-equilibrated aqueous solution of PteGlu is exposed to UV-A radiation, the rate of the degradation increases with irradiation time. The mechanism involved in this “auto-photo-catalytic” effect was investigated in aqueous solutions using a variety of tools. Whereas PteGlu is photostable under anaerobic conditions, it is converted into 6-formylpterin (Fop) and p-aminobenzoyl-L-glutamic acid (PABA-Glu) in the presence of oxygen. As the reaction proceeds and enough Fop accumulates in the solution, a photosensitized electron-transfer process starts, where Fop photoinduces the oxidation of PteGlu to Fop, and H₂O₂ is formed. This process also takes place with other pterins as photosensitizers. The results are discussed with the context of previous mechanisms for processes photosensitized by pterins, and their biological implications are evaluated. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas |
description |
Folic acid, or pteroyl-L-glutamic acid (PteGlu), is a precursor of coenzymes involved in the metabolism of nucleotides and amino acids. PteGlu is composed of three moieties: a 6-methylpterin (Mep) residue, a p-aminobenzoic acid (PABA) residue, and a glutamic acid (Glu) residue. Accumulated evidence indicates that photolysis of PteGlu leads to increased risk of several pathologies. Thus, a study of PteGlu photodegradation can have significant ramifications. When an air-equilibrated aqueous solution of PteGlu is exposed to UV-A radiation, the rate of the degradation increases with irradiation time. The mechanism involved in this “auto-photo-catalytic” effect was investigated in aqueous solutions using a variety of tools. Whereas PteGlu is photostable under anaerobic conditions, it is converted into 6-formylpterin (Fop) and p-aminobenzoyl-L-glutamic acid (PABA-Glu) in the presence of oxygen. As the reaction proceeds and enough Fop accumulates in the solution, a photosensitized electron-transfer process starts, where Fop photoinduces the oxidation of PteGlu to Fop, and H₂O₂ is formed. This process also takes place with other pterins as photosensitizers. The results are discussed with the context of previous mechanisms for processes photosensitized by pterins, and their biological implications are evaluated. |
publishDate |
2010 |
dc.date.none.fl_str_mv |
2010-12 |
dc.type.none.fl_str_mv |
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article |
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http://sedici.unlp.edu.ar/handle/10915/144468 |
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http://sedici.unlp.edu.ar/handle/10915/144468 |
dc.language.none.fl_str_mv |
eng |
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eng |
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