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ToolsBernhardt, Peter and O'Connor, Sarah E. (2009) Synthesis and biochemical evaluation of des-vinyl secologanin aglycones with alternate stereochemistry. Tetrahedron Letters, 50 (51). pp. 7118-7120.
Full text not available from this repository.Abstract
Based on the X-ray structure of the enzyme strictosidine synthase, the glucose moiety of the seco-iridoid glucoside, secologanin, appears to be the key for orienting the substrate. We hypothesized that removing the glucose moiety would allow alternate stereoisomers of secologanin to be turned over. A convenient synthesis to prepare stereoisomers of des-vinyl secologanin is presented. The choice of protective group was the key to access this series of compounds. The analogs were assayed with strictosidine synthase and, interestingly, both the natural 2,4-trans diastereomer and the unnatural 2,4-cis diastereomer are turned over. The trans/cis selectivity increases with increased acetal substituent size. The results add to our understanding of how strictosidine synthase discriminates among stereoisomers.
| Item Type: | Article |
|---|---|
| Faculty \ School: | Faculty of Science > School of Chemistry |
| UEA Research Groups: | Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) |
| Depositing User: | Rhiannon Harvey |
| Date Deposited: | 21 Mar 2012 14:10 |
| Last Modified: | 11 Mar 2024 00:42 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/38406 |
| DOI: | 10.1016/j.tetlet.2009.09.171 |
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