Pyrrole Aminoimidazole Alkaloid Metabiosynthesis with Marine Sponges Agelas conifera and Stylissa caribica

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 CC...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 51; no. 20; pp. 4877 - 4881
Main Authors:	Stout, E. Paige, Wang, Yong-Gang, Romo, Daniel, Molinski, Tadeusz F.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 14-05-2012 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Edition:	International ed. in English
Subjects:	Agelas - chemistry Agelas - metabolism alkaloids Alkaloids - biosynthesis Alkaloids - chemical synthesis Animals biosynthesis electron transfer Imidazoles - chemical synthesis Imidazoles - metabolism metabiosynthesis natural products Porifera - chemistry Porifera - metabolism Pyrroles - chemical synthesis Pyrroles - metabolism
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Summary:	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 CC bond‐forming reactions of precursors.
Bibliography:	NIH - No. GM052964; No. NIH/NCI T32 CA009523 ark:/67375/WNG-XJG7XLM3-T ArticleID:ANIE201108119 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. istex:C7631907B2A5FA1997193EFD8114BDD645782D23 RV 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 Cape Hatteras for logistical support during collecting expeditions and in‐field assays. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201108119