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J Nat Prod. 2012 Apr 27;75(4):527-30. doi: 10.1021/np300051k. Epub 2012 Mar 28.

De novo synthesis of benzosceptrin C and nagelamide H from 7-15N-oroidin: implications for pyrrole-aminoimidazole alkaloid biosynthesis.

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1
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.

Abstract

De novo synthesis of the natural products benzosceptrin C (7) and nagelamide H (8) was achieved using cell-free enzyme preparations from the marine sponges Agelas sceptrum and Stylissa caribica employing synthetic 7-(15)N-oroidin. These studies provide direct experimental evidence to support the long-standing, but untested, hypothesis that oroidin is a precursor to more complex pyrrole-aminoimidazole alkaloids, such as the sceptrins, benzosceptrins, and nagelamides. In addition, a new nagelamide, didebromonagelamide A (5b), was isolated from S. caribica, representing the first report of a nagelamide-like compound from the Caribbean.

PMID:
22455452
PMCID:
PMC3694594
DOI:
10.1021/np300051k
[Indexed for MEDLINE]
Free PMC Article
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