Computational Modeling of the Optical Rotation of Amino Acids: An 'in Silico' Experiment for Physical Chemistry.

A computational experiment that investigates the optical activity of the amino acid valine has been developed for an upper-level undergraduate physical chemistry laboratory course. Hybrid density functional theory calculations were carried out for valine to confirm the rule that adding a strong acid to a solution of an amino acid in the L configuration renders the optical rotation more positive. Correspondingly, if the optical rotation becomes more negative, the amino acid is of the D configuration. The students employed the open-source molecular editor Avogadro to build the molecules, conduct conformer searches, and calculate the energies of the conformers with a molecular mechanics force field. Subsequent geometry optimizations and optical rotation calculations were performed with a quantum chemistry program, using the WebMO graphical interface. The role of the solvent in stabilizing the zwitterionic form of an amino acid was investigated. [ABSTRACT FROM AUTHOR]