Synthesis, Characterization, and Photocleavage of Bis ‐Decyl Pteroic Acid: A Folate Derivative with Affinity to Biomembranes

FONSECA, JOSÉ LUIS; SOSA, M. JOSÉ; PETROSELLI, GABRIELA; ERRA-BALSELLS, ROSA; QUINDT, MATÍAS I.; BONESI, SERGIO M.; GREER, ALEXANDER; GREER, EDYTA M.; THOMAS, ANDRÉS H.; VIGNONI, MARIANA

PHOTOCHEMISTRY AND PHOTOBIOLOGY

WILEY-BLACKWELL PUBLISHING, INC

Año: 2022

0031-8655

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.