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Biosynthetic O-Methylation Protects Cladoniamides from Self-destruction.

TitleBiosynthetic O-Methylation Protects Cladoniamides from Self-destruction.
Publication TypeJournal Article
Year of Publication2013
AuthorsDu, YLing, Ding, T, Ryan, KS
JournalOrganic letters
Volume15
Start Page2538
Pagination2538–2541
Date Published2013 May 2
ISSN1523-7052
Abstract

Bisindole cladoniamides, nanomolar inhibitors of colon cancer cell line HCT-116, contain a rare, indolotryptoline substructure. In this report, the structures of xenocladoniamides A-E (9-13) are described. Compounds 9-13 are generated from a cladoniamide heterologous production system where O-methyltransferase gene claM3 has been inactivated. The results suggest that O-methylation, installed by enzyme ClaM3, is critical to maintaining the structural integrity of the indolotryptoline scaffold. Xenocladoniamides D and E are modestly cytotoxic against colon cancer cell line HCT-116.

DOI10.1021/ol401036f