Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy- p -menthane as a Case Study

In this study, the computational analysis of electronic circular dichroism (ECD) spectra and the employment of biphenyl chiroptical probes were compared in the absolute configuration assignment of (-)-1α,2α,3β-trihydroxy- -menthane ( ), taken as a representative example of a UV-transparent chiral na...

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Bibliographic Details
Published in:Biomolecules (Basel, Switzerland) Switzerland), 2022-03, Vol.12 (3), p.421
Main Authors: Marsico, Giulia, Calice, Umberto, Scafato, Patrizia, Belviso, Sandra, Evidente, Antonio, Superchi, Stefano
Format: Article
Language:English
Subjects:
Absolute configuration
Biological activity
Biological Products
Biphenyl
biphenyls
chiral natural products
chiroptical probes
Chromatography
Circular Dichroism
Complementarity
Computer applications
electronic circular dichroism
Fungi
hydroxy menthane
Metabolites
Natural products
NMR
Nuclear magnetic resonance
p-Menthane
Probes
Spectroscopy
Spectrum analysis
Stereoisomerism
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Summary:In this study, the computational analysis of electronic circular dichroism (ECD) spectra and the employment of biphenyl chiroptical probes were compared in the absolute configuration assignment of (-)-1α,2α,3β-trihydroxy- -menthane ( ), taken as a representative example of a UV-transparent chiral natural product. The usefulness of chiroptical probes in the configurational assignments of natural products and their complementarity to the computational protocols is herein highlighted. The biphenyl probe approach proves to be straightforward, reliable, and suitable for conformationally mobile and ECD silent compounds, not treatable by computational analysis of chiroptical data.
ISSN:2218-273X
2218-273X
DOI:10.3390/biom12030421