Funding for this work from NIH (GM052964) and a Ruth L. Kirschstein National Research Service Award (NIH/NCI T32 CA009523) is gratefully acknowledged. We thank J. J. LaClair and M. Burkart for help with fluorescence spectra, B. Morinaka and Y. Su (UCSD) for NMR and HRMS measurements, respectively. We are grateful to J. Pawlik (UNC Wilmington), and the captain and crew of the RV Cape Hatteras for logistical support during collecting expeditions and in-field assays.
Pyrrole Aminoimidazole Alkaloid Metabiosynthesis with Marine Sponges Agelas conifera and Stylissa caribica†
Article first published online: 4 APR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 20, pages 4877–4881, May 14, 2012
How to Cite
Stout, E. P., Wang, Y.-G., Romo, D. and Molinski, T. F. (2012), Pyrrole Aminoimidazole Alkaloid Metabiosynthesis with Marine Sponges Agelas conifera and Stylissa caribica. Angew. Chem. Int. Ed., 51: 4877–4881. doi: 10.1002/anie.201108119
- Issue published online: 8 MAY 2012
- Article first published online: 4 APR 2012
- Manuscript Revised: 3 FEB 2012
- Manuscript Received: 18 NOV 2011
- NIH. Grant Numbers: GM052964, NIH/NCI T32 CA009523
- electron transfer;
- natural products
Game-SET-match: Pyrrole aminoimidazole alkaloids (PAIs) are metabiosynthesized from chlorinated analogues of oroidin by cell-free enzyme preparations from PAI-producing sponges. Evidence and implications for the biosynthesis of PAIs include putative single-electron transfers (SETs) that promote CC bond-forming reactions of precursors.