Chiroptical properties of streptorubin B: the synergy between theory and experiment
Marta S Andrade1, Vanessa S Silva1, Ana M Lourenço1
1Department of Chemistry, REQUIMTE/LAQV, Faculty of Sciences and Technology, Universidade NOVA de Lisboa, Caparica, Portugal.
Abstract:
Analysis of the calculated and measured optical rotation (OR) together with other calculated chiroptical properties such as electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of the prodigiosin alkaloid streptorubin B shows that these are dominated by the pseudoenantiomeric atropisomers anti-(S)-streptorubin B (1A) and syn-(S)-streptorubin (1B). Atropisomerism is a dynamic phenomenon with a potentially nonequilibrium population of isomers, and accordingly the measured chiroptical responses may vary with time, concentration, temperature, and the anion of the salts used. Streptorubin also has the potential to form stacked homodimers for which the optical rotations measured at 589 nm can vary greatly due to the presence of ECD-active electronic transitions in this region.
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