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ACS Chem Biol. 2013 May 17;8(5):877-83. doi: 10.1021/cb300614c. Epub 2013 Feb 22.

Aestuaramides, a natural library of cyanobactin cyclic peptides resulting from isoprene-derived Claisen rearrangements.

Abstract

We report 12 cyanobactin cyclic peptides, the aestuaramides, from the cultivated cyanobacterium Lyngbya aestuarii. We show that aestuaramides are synthesized enzymatically as reverse O-prenylated tyrosine ethers that subsequently undergo a Claisen rearrangement to produce forward C-prenylated tyrosine. These results reveal that a nonenzymatic Claisen rearrangement dictates isoprene regiochemistry in a natural system. They also reveal one of the mechanisms that organisms use to generate structurally diverse compound libraries starting from simple ribosomal peptide pathways (RiPPs).

PMID:
23411099
PMCID:
PMC3657307
DOI:
10.1021/cb300614c
[Indexed for MEDLINE]
Free PMC Article
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