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The application of nuclear magnetic resonance in the structural elucidation of natural products
Includes bibliographical references.
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| Main Author: | |
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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
| Published: |
Department of Chemistry
2015
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| _version_ | 1867613303171186688 |
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| access_status_str | Open Access |
| author | Nair, Margie May |
| author2 | Jackson, Graham Ellis |
| author_browse | Jackson, Graham Ellis Nair, Margie May |
| author_facet | Jackson, Graham Ellis Nair, Margie May |
| author_sort | Nair, Margie May |
| collection | Thesis |
| description | Includes bibliographical references. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/16004 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:33:59.204Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2015 |
| publishDateRange | 2015 |
| publishDateSort | 2015 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/16004 The application of nuclear magnetic resonance in the structural elucidation of natural products Nair, Margie May Jackson, Graham Ellis Chemistry Includes bibliographical references. Multipulse Nuclear Magnetic Resonance (NMR) techniques were investigated via structural assignment of various natural products. The natural products chosen for investigation of 2D NMR spectroscopy as a structural tool were the opium alkaloids codeine and papaverine, the diterpenoid alkaloids delphinine and aconitine and the triterpenoid derivatives of cucurbitaceae. One dimensional NMR spectroscopy viz 1H, 13C and Distortionless Enhancement by Polarisation Transfer (DEPT) spectroscopy was initially applied to obtain a level of indication of the complexity of the structural problem solving. Various multipulse techniques were chosen depending on the sample quantity available, the sensitivity of the technique, the information provided and its applicabilty in the field of natural products. Both homonuclear scalar and dipolar correlation as well as short and long range heteronuclear correlation was investigated. The homonuclear Correlation Spectroscopy (COSY) experiment which revealed scalar 1H-1H scalar correlations was adequate for the structural assignment. The Heteronuclear Multiple Quantum Coherence (HMQC) experiment offered greater sensitivity on small sample quantities whilst the long range Heteronuclear Correlation (HETCOR) and Heteronuclear Multiple Bond Coherence (HMBC) experiments were essential for complete assignment of the quaternary groups. The stereochemical designation of some of the compounds was confirmed using the Rotating Frame Overhauser Enhancement Spectroscopy (ROESY) experiment which proved to be a more applicable pulse sequence for the natural products under investigation. The 1H and 13C assignments of these derivatives and the experimental approach used to obtain this data was compared to that present in the literature. The results indicate that apart from offering tremendous versatility depending on the special attributes of the compound, two dimensional NMR techniques are imperative for the unambiguous structural assignment of natural products. 2015-12-28T06:11:09Z 2015-12-28T06:11:09Z 1994 Master Thesis Masters MSc http://hdl.handle.net/11427/16004 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Nair, Margie May The application of nuclear magnetic resonance in the structural elucidation of natural products |
| thesis_degree_str | Master's |
| title | The application of nuclear magnetic resonance in the structural elucidation of natural products |
| title_full | The application of nuclear magnetic resonance in the structural elucidation of natural products |
| title_fullStr | The application of nuclear magnetic resonance in the structural elucidation of natural products |
| title_full_unstemmed | The application of nuclear magnetic resonance in the structural elucidation of natural products |
| title_short | The application of nuclear magnetic resonance in the structural elucidation of natural products |
| title_sort | application of nuclear magnetic resonance in the structural elucidation of natural products |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/16004 |
| work_keys_str_mv | AT nairmargiemay theapplicationofnuclearmagneticresonanceinthestructuralelucidationofnaturalproducts AT nairmargiemay applicationofnuclearmagneticresonanceinthestructuralelucidationofnaturalproducts |