Work

Aestuaramides, a Natural Library of Cyanobactin Cyclic Peptides Resulting from Isoprene-Derived Claisen Rearrangements

Year: 2013

Type: article

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).

Source: ACS Chemical Biology

DOI: 10.1021/cb300614c

Authors: John A. McIntosh, Zhenjian Lin, Ma. Diarey B. Tianero, Eric W. Schmidt

Institution: University of Utah

Language: English

Topic: Microbial Natural Products and Biosynthesis

Subfield: Pharmacology

Field: Medicine

Domain: Health Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: G1192692190, Symbiont Models for Natural Product Pathway Manipulation, G635527312, Rapid Screening and Dereplication of Marine Symbiotic Natural Products