Journal
ORGANIC LETTERS
Volume 13, Issue 5, Pages 1202-1205Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2000843
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Funding
- BBSRC [BB/G003572/1]
- Cardiff University
- Biotechnology and Biological Sciences Research Council [BB/G003572/1] Funding Source: researchfish
- BBSRC [BB/G003572/1] Funding Source: UKRI
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Trigonal iminium halides of (4aS,7S)-1,4a-dimethyl- and (4aS,7S)-4a-methyl-7-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydroquinolinium ions, aimed to mimic transition states associated with the aristolochene synthase-catalyzed cyclization of (-)-germacrene A to eudesmane cation, were evaluated under standard kinetic steady-state conditions. In the presence of inorganic diphosphate, these analogues were shown to competitively inhibit the enzyme, suggesting a stabilizing role for the diphosphate leaving group in this apparently endothermic transformation.
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