title: Chiroptical properties of streptorubin B: the synergy between theory and experiment.
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.
authors: Department of Chemistry, REQUIMTE/LAQV, Faculty of Sciences and Technology, Universidade NOVA de Lisboa, Caparica, Portugal.
authors: Marta S
authors: MS
authors: Andrade
authors: Department of Chemistry, REQUIMTE/LAQV, Faculty of Sciences and Technology, Universidade NOVA de Lisboa, Caparica, Portugal.
authors: Vanessa S
authors: VS
authors: Silva
authors: Department of Chemistry, REQUIMTE/LAQV, Faculty of Sciences and Technology, Universidade NOVA de Lisboa, Caparica, Portugal.
authors: Ana M
authors: AM
authors: Lourenço
authors: Department of Chemistry, REQUIMTE/LAQV, Faculty of Sciences and Technology, Universidade NOVA de Lisboa, Caparica, Portugal.
authors: Ana M
authors: AM
authors: Lobo
authors: Department of Chemistry, Imperial College London, South Kensington Campus, Exhibition Road, London, UK.
authors: Henry S
authors: HS
authors: Rzepa
mesh_terms: D002942:Circular Dichroism; D019281:Dimerization; D008958:Models, Molecular; D008968:Molecular Conformation; D009904:Optical Rotation; D011353:Prodigiosin / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C528939:streptorubin B; D011353:Prodigiosin
keywords: ECD; ORP; TDDFT calculations; VCD; atropisomers; chiroptical properties; prodigiosins; pseudoenantiomers; streptorubin B