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Angew Chem Int Ed Engl

Title:		Modular Chemoenzymatic Synthesis of Terpenes and their Analogues
Author(s):		Johnson LA; Dunbabin A; Benton JCR; Mart RJ; Allemann RK;
Address:		"School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK"
Journal Title:		Angew Chem Int Ed Engl
Year:		2020
Volume:		20200325
Issue:		22
Page Number:		8486 - 8490
DOI:		10.1002/anie.202001744
ISSN/ISBN:		1521-3773 (Electronic) 1433-7851 (Linking)
Abstract:		"Non-natural terpenoids offer potential as pharmaceuticals and agrochemicals. However, their chemical syntheses are often long, complex, and not easily amenable to large-scale production. Herein, we report a modular chemoenzymatic approach to synthesize terpene analogues from diphosphorylated precursors produced in quantitative yields. Through the addition of prenyl transferases, farnesyl diphosphates, (2E,6E)-FDP and (2Z,6Z)-FDP, were isolated in greater than 80 % yields. The synthesis of 14,15-dimethyl-FDP, 12-methyl-FDP, 12-hydroxy-FDP, homo-FDP, and 15-methyl-FDP was also achieved. These modified diphosphates were used with terpene synthases to produce the unnatural sesquiterpenoid semiochemicals (S)-14,15-dimethylgermacrene D and (S)-12-methylgermacrene D as well as dihydroartemisinic aldehyde. This approach is applicable to the synthesis of many non-natural terpenoids, offering a scalable route free from repeated chain extensions and capricious chemical phosphorylation reactions"
Keywords:		"Chemistry Techniques, Synthetic Dimethylallyltranstransferase/*metabolism Phosphorylation Polyisoprenyl Phosphates/chemistry Sesquiterpenes/chemistry Terpenes/*chemical synthesis/*chemistry biocatalysis chemoenzymatic synthesis natural products terpenoids;"
Notes:		"MedlineJohnson, Luke A Dunbabin, Alice Benton, Jennifer C R Mart, Robert J Allemann, Rudolf K eng BB/M006158/1/BB_/Biotechnology and Biological Sciences Research Council/United Kingdom BB/M022463/1/BB_/Biotechnology and Biological Sciences Research Council/United Kingdom BB/N012526/1/BB_/Biotechnology and Biological Sciences Research Council/United Kingdom BB/P009980/1/BB_/Biotechnology and Biological Sciences Research Council/United Kingdom BB/R019681/1/BB_/Biotechnology and Biological Sciences Research Council/United Kingdom Research Support, Non-U.S. Gov't Germany 2020/02/28 Angew Chem Int Ed Engl. 2020 May 25; 59(22):8486-8490. doi: 10.1002/anie.202001744. Epub 2020 Mar 25"