Synthesis and biochemical evaluation of des-vinyl secologanin aglycones with alternate stereochemistry

Bernhardt, P and O'Connor, SE (2009) Synthesis and biochemical evaluation of des-vinyl secologanin aglycones with alternate stereochemistry. Tetrahedron Letters, 50 (51). pp. 7118-7120.

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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
University of East Anglia > Faculty of Science > Research Groups > Synthetic Chemistry
Related URLs:
Depositing User: Rhiannon Harvey
Date Deposited: 21 Mar 2012 14:10
Last Modified: 25 Jul 2018 04:36
URI: https://ueaeprints.uea.ac.uk/id/eprint/38406
DOI: 10.1016/j.tetlet.2009.09.171

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