Computational studies on tautomers of fluorinated-histidine and fluorinated-imidazole
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Kasireddy, Chandana. 2014. Computational Studies on Tautomers of Fluorinated-Histidine and Fluorinated-Imidazole. -- In Proceedings: 10th Annual Symposium on Graduate Research and Scholarly Projects. Wichita, Ks: Wichita State University, p. 109
Fluorinated amino acids are playing an important role in understanding protein-protein interactions, protein folding and protein structure function. Since histidine contains an imidazole ring, we considered the N1-H and N3-H tautomers of 2F-histidine and 4F-histidine, 2F-imidazole and 4F-imidazole, and calculated free energies and 19F NMR shifts in water and acetonitrile. The calculations were performed by the COSMO solvation model with B3LYP method 6-31++G(d) using Gaussian09 software. The calculations showed that the relative stabilities of the four isomers of fluorohistidine are consistent in both the solvents. The same trend is observed for fluoroimidazole isomers.The 19F NMR calculations showed different chemical shifts from zwitterionic/neutral to protonated forms for N1-H and N3-H tautomers of fluorohistidine and fluoroimidazole.
Presented to the 10th Annual Symposium on Graduate Research and Scholarly Projects (GRASP) held at the Heskett Center, Wichita State University, April 25, 2014.
Research completed at Department of Chemistry, College of Liberal Arts and Sciences