Abstract
The determination of the predominant tautomeric form of folate in solution is addressed theoretically and experimentally. DFT and atomistic molecular dynamics simulations are used to compare the most stable tautomers of folate. B3LYP/6–311+G(d) model chemistry shows that the lactam form of folate FA-N3 is the most energetically favorable tautomer. The lactam FA-N1 differs by about 2.5 kcal/mol. The conformation of the molecule does not influence markedly the energy ordering of the tautomers. Molecular dynamics results for the two lactams in saline outline similar behavior of the two molecules and flexible docking predicts comparable interactions with the folate receptor-α (FR-α). 1H NMR spectra of folic acid in water and DMSO also identify the lactam tautomers as present in the solutions. Both 1H and 13C chemical shifts show fast exchange of protons between the N1 and N3 positions of pterin.
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