Mimicking Dimethylallyltryptophan Synthase: Experimental Evidence for a Biosynthetic Cope Rearrangement Process | Zendy

Schwarzer Darius D. | Zendy; Gritsch Philipp J. | Zendy; Gaich Tanja | Zendy

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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.

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