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(R)-Metacycloprodigiosin-HCl: Chiroptical properties and structure
Daniela Peixoto1, Elisabete P Ferreira1, Ana M Lourenço1
1Department of Chemistry, REQUIMTE/LAQV & UCIBIO, NOVA University of Lisbon, Caparica, Portugal.
Chirality
|May 11, 2018
Summary
The study reveals that anti-(R)-metacycloprodigiosin-HCl (1b) is the predominant tautomer, supported by computational and experimental data. This finding is crucial for understanding prodigiosin derivatives and their chiroptical properties.
Area of Science:
- Organic Chemistry
- Computational Chemistry
- Spectroscopy
Background:
- Prodigiosins are natural pigments with diverse biological activities.
- (R)-Metacycloprodigiosin exhibits tautomerism, leading to structural complexity.
- Understanding tautomeric forms is key to elucidating structure-activity relationships.
Purpose of the Study:
- To investigate the tautomeric equilibrium and chiroptical properties of (R)-metacycloprodigiosin-HCl.
- To determine the predominant tautomeric form and its conformers.
- To compare computational predictions with experimental spectroscopic data.
Main Methods:
- Density Functional Theory (DFT) calculations at the B3LYP/6-311++G(2d,2p) level.
- Calculation of energetics, electronic circular dichroism (ECD), and specific optical rotation (SOR).
- Measurement of experimental ECD spectra and SOR.
Main Results:
- The anti-(R)-metacycloprodigiosin-HCl (1b) tautomer is energetically favored over the syn form (1a).
- Calculated SOR and ECD spectra for 1b closely match experimental observations.
- Nuclear Overhauser Effect (NOE) data supports the predominance of the anti-tautomer.
Conclusions:
- Anti-(R)-metacycloprodigiosin-HCl (1b) is the predominant tautomer in solution.
- Computational methods accurately predict the chiroptical properties of prodigiosin derivatives.
- The findings provide insights into the structural behavior of prodigiosins and related compounds.
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