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Mimicking Dimethylallyltryptophan Synthase: Experimental Evidence for a Biosynthetic Cope Rearrangement Process
Author(s) -
Schwarzer Darius D.,
Gritsch Philipp J.,
Gaich Tanja
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201203586
Subject(s) - atp synthase , sigmatropic reaction , cope rearrangement , chemistry , enzyme , nucleus , indole test , stereochemistry , biosynthesis , transformation (genetics) , biochemistry , biology , microbiology and biotechnology , gene
Easy to cope with : Experimental evidence was found to support an enzymatic [3,3]‐sigmatropic rearrangement catalyzed by dimethylallyltryptophan (DMAT) synthase (see scheme). A bio‐inspired system showed the feasibility of Cope rearrangement to the C‐4 position of the indole nucleus. The tricyclic benzo[ cd ]indole core of welwitindolinones and dragmacidin E was synthesized using this transformation.