Full Text Available
Note: Clicking the button above will open the full text document at the original institutional repository in a new window.
Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme
Dissertation (MSc)--University of Pretoria, 1992.
Saved in:
| Other Authors: | |
|---|---|
| Format: | Thesis |
| Language: | English |
| Published: |
University of Pretoria
2022
|
| Subjects: | |
| Tags: |
No Tags, Be the first to tag this record!
|
| _version_ | 1867613662805491712 |
|---|---|
| access_status_str | Open Access |
| author2 | Vleggaar, Robert |
| author_browse | Vleggaar, Robert |
| author_facet | Vleggaar, Robert |
| collection | Thesis |
| dc_rights_str_mv | © 2020 University of Pretoria. All rights reserved. The copyright in this work vests in the University of Pretoria. No part of this work may be reproduced or transmitted in any form or by any means, without the prior written permission of the University of Pretoria. |
| description | Dissertation (MSc)--University of Pretoria, 1992. |
| format | Thesis |
| id | oai:repository.up.ac.za:2263/85348 |
| institution | University of Pretoria (South Africa) |
| language | English |
| last_indexed | 2026-06-10T12:39:43.129Z |
| license_str | Other — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UPSpace — University of Pretoria Institutional Repository |
| publishDate | 2022 |
| publishDateRange | 2022 |
| publishDateSort | 2022 |
| publisher | University of Pretoria |
| publisherStr | University of Pretoria |
| record_format | dspace |
| source_str | UPSpace — University of Pretoria Institutional Repository |
| spelling | oai:repository.up.ac.za:2263/85348 Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme Vleggaar, Robert Horak, R.M. Boer, Annarie UCTD Stereochemical Fumonisins Metabolites Fusarium moniliforme Dissertation (MSc)--University of Pretoria, 1992. Fusarium moniliforme, a common fungal contaminant of maize, has been implicated as the causative agent in human oesophageal cancer in the Transkei as well as equine leukoencephalomalacia in horses worldwide. Previous studies established that the fumonisins, a family of structurally related mycotoxins isolated from cultures of F. moniliforme, are the diesters of propane- 1 ,2,3-tricarboxylic acid and either 2-acetylamino- or 2-amino-1 2, 1 6-dimethyl- 3 ,5, 10, 14, 15-pentahydroxyicosane as well as in each case the C-10 deoxy analogue. In all cases both the C-14 and C-1 5 hydroxy groups are involved in ester formation. In the present study the mode of linkage of the propane-1,2,3-tricarboxylic acid groups to the C-14 and C-1 5 hydroxy groups in the fumonisin molecule was studied by selective reduction of the ester functionalities with sodium borohydride and subsequent characterization of the lactone. In this way it was established that in each case a terminal carboxy group of propane-1 ,2,3-tricarboxylic acid is involved in the ester linkage. The relative configuration of the different chiral centres present in the fumonisins was deduced from proton-proton coupling constants and proton-proton n.O.e. studies on 2,2-dimethyl-1 ,3-dioxolane, 1 ,3-dioxane, 2,2-dimethyl-1 ,3-dioxane and 2-oxazolidinone derivatives. The absolute configuration of the C-10 and C-5 chiral centres was determined by the method of Horeau. Oxidative cleavage of the C-14-C-15 dial moiety and comparison of the a-methyl-p-nitrobenzylamide derivative of the 2-methylhexanoic acid formed with a standard, established the absolute configuration at C-1 6. The stereochemical studies established the absolute configuration of fumonisin 8 1 as (2S,3S,5R, 1 OR, 12S, 14S, 15R, 16R)-1, 1 '-[14, 15-(2-amino-3,5, 1 0-trihydroxy-12, 16- dimethylicosandiyl)] di-(2,3-dihydrogen propane-1 ,2 ,3-tricarboxylate). Geology MSc Unrestricted 2022-05-17T11:20:21Z 2022-05-17T11:20:21Z 6/8/2021 1992 Dissertation * https://repository.up.ac.za/handle/2263/85348 en © 2020 University of Pretoria. All rights reserved. The copyright in this work vests in the University of Pretoria. No part of this work may be reproduced or transmitted in any form or by any means, without the prior written permission of the University of Pretoria. application/pdf University of Pretoria |
| spellingShingle | UCTD Stereochemical Fumonisins Metabolites Fusarium moniliforme Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme |
| title | Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme |
| title_full | Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme |
| title_fullStr | Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme |
| title_full_unstemmed | Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme |
| title_short | Stereochemical studies on the fumonisins, metabolites of fusarium moniliforme |
| title_sort | stereochemical studies on the fumonisins metabolites of fusarium moniliforme |
| topic | UCTD Stereochemical Fumonisins Metabolites Fusarium moniliforme |
| url | https://repository.up.ac.za/handle/2263/85348 |