Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-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-<i>p</i>-menthane (<b>1</b>), taken as a representative...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-03-01
|
| Series: | Biomolecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2218-273X/12/3/421 |
| _version_ | 1797472641357971456 |
|---|---|
| author | Giulia Marsico Umberto Calice Patrizia Scafato Sandra Belviso Antonio Evidente Stefano Superchi |
| author_facet | Giulia Marsico Umberto Calice Patrizia Scafato Sandra Belviso Antonio Evidente Stefano Superchi |
| author_sort | Giulia Marsico |
| collection | DOAJ |
| description | 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-<i>p</i>-menthane (<b>1</b>), 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. |
| first_indexed | 2024-03-09T20:05:15Z |
| format | Article |
| id | doaj.art-dabb86d4a1d1494e8719ce2576d58db4 |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-03-09T20:05:15Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-dabb86d4a1d1494e8719ce2576d58db42023-11-24T00:35:43ZengMDPI AGBiomolecules2218-273X2022-03-0112342110.3390/biom12030421Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-menthane as a Case StudyGiulia Marsico0Umberto Calice1Patrizia Scafato2Sandra Belviso3Antonio Evidente4Stefano Superchi5Department of Sciences, University of Basilicata, Via dell’Ateneo Lucano 10, 85100 Potenza, ItalyDepartment of Sciences, University of Basilicata, Via dell’Ateneo Lucano 10, 85100 Potenza, ItalyDepartment of Sciences, University of Basilicata, Via dell’Ateneo Lucano 10, 85100 Potenza, ItalyDepartment of Sciences, University of Basilicata, Via dell’Ateneo Lucano 10, 85100 Potenza, ItalyDepartment of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte Sant’Angelo, Via Cintia 4, 80126 Napoli, ItalyDepartment of Sciences, University of Basilicata, Via dell’Ateneo Lucano 10, 85100 Potenza, ItalyIn 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-<i>p</i>-menthane (<b>1</b>), 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.https://www.mdpi.com/2218-273X/12/3/421hydroxy menthanechiral natural productsabsolute configurationbiphenylschiroptical probeselectronic circular dichroism |
| spellingShingle | Giulia Marsico Umberto Calice Patrizia Scafato Sandra Belviso Antonio Evidente Stefano Superchi Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-menthane as a Case Study Biomolecules hydroxy menthane chiral natural products absolute configuration biphenyls chiroptical probes electronic circular dichroism |
| title | Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-menthane as a Case Study |
| title_full | Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-menthane as a Case Study |
| title_fullStr | Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-menthane as a Case Study |
| title_full_unstemmed | Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-menthane as a Case Study |
| title_short | Computational Approaches and Use of Chiroptical Probes in the Absolute Configuration Assignment to Natural Products by ECD Spectroscopy: A 1,2,3-Trihydroxy-<i>p</i>-menthane as a Case Study |
| title_sort | computational approaches and use of chiroptical probes in the absolute configuration assignment to natural products by ecd spectroscopy a 1 2 3 trihydroxy i p i menthane as a case study |
| topic | hydroxy menthane chiral natural products absolute configuration biphenyls chiroptical probes electronic circular dichroism |
| url | https://www.mdpi.com/2218-273X/12/3/421 |
| work_keys_str_mv | AT giuliamarsico computationalapproachesanduseofchiropticalprobesintheabsoluteconfigurationassignmenttonaturalproductsbyecdspectroscopya123trihydroxyipimenthaneasacasestudy AT umbertocalice computationalapproachesanduseofchiropticalprobesintheabsoluteconfigurationassignmenttonaturalproductsbyecdspectroscopya123trihydroxyipimenthaneasacasestudy AT patriziascafato computationalapproachesanduseofchiropticalprobesintheabsoluteconfigurationassignmenttonaturalproductsbyecdspectroscopya123trihydroxyipimenthaneasacasestudy AT sandrabelviso computationalapproachesanduseofchiropticalprobesintheabsoluteconfigurationassignmenttonaturalproductsbyecdspectroscopya123trihydroxyipimenthaneasacasestudy AT antonioevidente computationalapproachesanduseofchiropticalprobesintheabsoluteconfigurationassignmenttonaturalproductsbyecdspectroscopya123trihydroxyipimenthaneasacasestudy AT stefanosuperchi computationalapproachesanduseofchiropticalprobesintheabsoluteconfigurationassignmenttonaturalproductsbyecdspectroscopya123trihydroxyipimenthaneasacasestudy |