Synthesis and characterization of long chain pterin derivatives: O vs. N substitution.

VIGNONE M.; WALALAWELA N.; GHAGORE C.; BONESI S. M.; THOMAS A.; GREER A.

Tampa

Congreso; ASP Conference 2016; 2016

ASP Conference 2016

We describe a synthetic process for the NandOalkylationof 2aminopteridin4(3H)one(pterin) by nucleophilic substitution (SN2). A decane chain wasintroduced either at N or O of the amide leading to two new alkylated pterins. Dialkylation of both N and O amide pterin sites was not observed. However,two adducts from Naminecondensation of dimethylformamide (DMF) were obtained as byproductssince DMF was used as solvent. The new pterinderivatives were characterized by NMR and mass spectrometry, and also absorption and emission spectra, fluorescence lifetime and singlet oxygenproduction were measured. The use of pH changes and comparison to the Nmethylatedpterin (2amino3methylpteridin4(3H)one),which exists in theketo form lacking the acidic NH, was key to assessing the alkylation at N and O positions in the new pterins. Unlike typical pterins, our new long chainpterins show lipophilic solubility, making them potential fluorescent probes in cell membranes.