Chiroptical Properties of Streptorubin B

The Synergy Between Theory and Experiment

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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. Chirality 27:745-751, 2015. (c) 2015 Wiley Periodicals, Inc.
Original languageEnglish
Pages (from-to)745-751
Number of pages7
JournalChirality
Volume27
Issue number0899-0042
DOIs
Publication statusPublished - Oct 2015

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Keywords

  • prodigiosins
  • streptorubin B
  • atropisomers
  • pseudoenantiomers
  • chiroptical properties
  • ORP
  • ECD
  • VCD
  • TDDFT calculations

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