This work was financially supported by the BMBF GenoMik program and by a Humboldt research fellowship to A.S. We are grateful to Dr. P. Krastel, Novartis, for the kind gift of the benastatin producer. We thank A. Perner and F. A. Gollmick for MS and NMR measurements, respectively.
Geminal Bismethylation Prevents Polyketide Oxidation and Dimerization in the Benastatin Pathway†
Article first published online: 9 AUG 2007
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 37, pages 7035–7038, September 17, 2007
How to Cite
Schenk, A., Xu, Z., Pfeiffer, C., Steinbeck, C. and Hertweck, C. (2007), Geminal Bismethylation Prevents Polyketide Oxidation and Dimerization in the Benastatin Pathway. Angew. Chem. Int. Ed., 46: 7035–7038. doi: 10.1002/anie.200702033
- Issue published online: 11 SEP 2007
- Article first published online: 9 AUG 2007
- Manuscript Received: 8 MAY 2007
- natural products;
A 'gem' of an enzyme: Geminal enzymatic bismethylation in the biosynthetic pathway leading to the cytotoxic polyketide benastatin blocks the highly reactive benzylic position of an anthrone-type intermediate. In a mutant lacking the C-methyl transferase, quinones and structurally intriguing meso and rac dimers (see calculated structure) are formed, which were elucidated by a combination of spectroscopy and computational simulations.