Carcinogenic Fried Foods: An ab initio computational study of a model decarboxylated Schiff base of Asparagine as a precursor in carcinogenic acrylamide formation

Frank Y. Gao, Amro H. Dodin, Harun Mustafaa, Natalie J. Galant, Imre G. Csizmadia

Abstract


Ab initio computations at the B3LYP/6-31G(d,p) level of theory have been performed on a model of a decarboxylated Schiff Base of Asparagine. Potential Energy Surfaces (PES) scans across two dihedrals, ψ and ϕ, of the endo and exo isomers of a sample molecule were performed. Stabilization is seen in [s, s] conformer of the exo isomer due to hydrogen bonding between opposing carbonyl and amine groups, whereas the endo isomer sees rapid destabilization in the same conformation due to steric strain between the carbonyl oxygen and the terminal methylene group. However, there was no notable free energy difference between the minimum energy conformers of the endo and exo isomers although the endo isomer was slightly energetically favored. The work presented here lays the groundwork for further studies into decarboxylated Schiff Bases from reactions with various sugars. This in turn allows for further investigation of mechanisms of formation, providing a basis for comparison of proposed pathways.

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