Practical preparation of unsaturated very-long-chain fatty acids (VLCFAs) and very-long-chain alkene pollinator attractants.

Autor: Bohman B; School of Molecular Sciences, University of Western Australia, Perth, Australia. bjorn.bohman@slu.se.; Department of Plant Protection Biology, Swedish University of Agricultural Sciences, Lomma, Sweden. bjorn.bohman@slu.se., Bersch AJ; Department of Plant Evolutionary Biology, Institute of Biology, University of Hohenheim, Stuttgart, Germany., Flematti GR; School of Molecular Sciences, University of Western Australia, Perth, Australia., Schlüter PM; Department of Plant Evolutionary Biology, Institute of Biology, University of Hohenheim, Stuttgart, Germany.
Jazyk: angličtina
Zdroj: Scientific reports [Sci Rep] 2024 Aug 24; Vol. 14 (1), pp. 19694. Date of Electronic Publication: 2024 Aug 24.
DOI: 10.1038/s41598-024-70598-x
Abstrakt: To prepare very-long-chain fatty acids and alkenes (VLCFAs and VLC alkenes) that are known pollinator attractants for sexually deceptive orchids, and biosynthetic precursors thereof, we applied a methodology allowing us to prepare monounsaturated VLCFAs with chain lengths up to 28 carbons and VLC alkenes up to 31 carbons. We implemented a coupling reaction between commercially available terminal alkynes and bromoalkanoic acids to prepare VLCFAs, allowing the products to be formed in two steps. For VLC alkenes, with many alkyltriphenylphosphonium bromides commercially available, we applied a Wittig reaction approach to prepare (Z)-configured monoenes in a single step. Using practical methods not requiring special reagents or equipment, we obtained 11 VLCFAs in > 90% isomeric purity, and 17 VLC alkenes in > 97% isomeric purity. Such general and accessible synthetic methods are essential for chemical ecology and biochemistry research to aid researchers in unambiguously identifying isolated semiochemicals and their precursors.
(© 2024. The Author(s).)
Databáze: MEDLINE
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