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Inhibition of (+)-Aristolochene Synthase with Iminium Salts Resembling Eudesmane Cation

Faraldos, Juan A. and Allemann, Rudolf Konrad 2011. Inhibition of (+)-Aristolochene Synthase with Iminium Salts Resembling Eudesmane Cation. Organic Letters 13 (5) , pp. 1202-1205. 10.1021/ol2000843

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Abstract

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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Cardiff Catalysis Institute (CCI)
Chemistry
Subjects: Q Science > QD Chemistry
Publisher: ACS
ISSN: 1523-7060
Funders: BBSRC
Last Modified: 04 Jun 2017 02:57
URI: http://orca.cf.ac.uk/id/eprint/14504

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