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

A new lipophilic folate derivative namelybis-decyl-Pte was synthesized, structurally and photophysically characterized. Decylation of pteroic acid (Pte) occurred at ketoO4 and at thep-aminobenzoic acid carboxylic acid group, pointing to a kinetically-controlled process based on results from DFT calculations. The photochemistry ofbis-decyl-Pte was investigated detecting a photocleavage attributed to a hydrolysis of the methylene bridge, as observed for Pte and folic acid. Moreover, asbis-decyl-Pte is able to interact with lipid membranes, efforts would be focused on investigating the photosensitizing properties of this compound and the photoproducts. AbstractHere, we provide mechanistic insight to the photocleavage of a compound in the folate family, namely pteroic acid. Abis-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 hypotheticalmono-,bis- andtris-decylated pteroic acid derivatives to help rationalize the regioselectivity of thebis-decyl pteroic acid product. Additionally, the lipophilicity of thebis-decyl pteroic acid appears to confer a hydrophobic property enabling an interaction with biomembranes.
Source: Photochemistry and Photobiology - Category: Science Authors: Tags: Special Issue Research Article Source Type: research