CIHIDECAR   12529
CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Unidad Ejecutora - UE
artículos
Título:
Synthesis, Characterization and Photocleavage of Bis-decyl Pteroic Acid: A Folate Derivative with Affinity to Biomembranes†
Autor/es:
FONSECA, JOSÉ LUIS; ERRA-BALSELLS, ROSA; GREER, ALEXANDER; VIGNONI, MARIANA; PETROSELLI, GABRIELA; BONESI, SERGIO M.; THOMAS, ANDRÉS H.; SOSA, M. JOSÉ; QUINDT, MATÍAS I.; GREER, EDYTA M.
Revista:
PHOTOCHEMISTRY AND PHOTOBIOLOGY
Editorial:
WILEY-BLACKWELL PUBLISHING, INC
Referencias:
Año: 2022 vol. 20 p. 1 - 12
ISSN:
0031-8655
Resumen:
Here, we provide mechanistic insight to the photocleavage of a compound in the folate family, namely pteroic acid. A bis-decyl chain derivative of pteroic acid was synthesized, structurally characterized, and photochemically investigated. We showed that, like folic acid, pteroic acid and the decylated derivative undergo a photocleavage reaction in the presence of H2O, while no reaction was observed in methanol solution. Furthermore, density functional theory calculations were carried out to predict relative stabilities of hypothetical mono-, bis-, and tris-decylated pteroic acid derivatives to help rationalize the regioselectivity of the bis-decyl pteroic acid product. Additionally, the lipophilicity of the bis-decyl pteroic acid appears to confer a hydrophobic property enabling an interaction with biomembranes.