Cylindrocyclophane Biosynthesis Involves Functionalization of an Unactivated Carbon Center

The cylindrocyclophanes are a family of natural products that share a remarkable paracyclophane carbon scaffold. Using genome sequencing and bioinformatic analyses, we have discovered a biosynthetic gene cluster involved in the assembly of cylindrocyclophane F. Through a combination of in vitro enzy...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-11, Vol.134 (45), p.18518-18521
Main Authors: Nakamura, Hitomi, Hamer, Hilary A, Sirasani, Gopal, Balskus, Emily P
Format: Article
Language:English
Subjects:
Carbon - chemistry
Carbon - metabolism
Computational Biology
Molecular Structure
Polycyclic Aromatic Hydrocarbons - chemistry
Polycyclic Aromatic Hydrocarbons - metabolism
Polyketide Synthases - metabolism
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Summary:The cylindrocyclophanes are a family of natural products that share a remarkable paracyclophane carbon scaffold. Using genome sequencing and bioinformatic analyses, we have discovered a biosynthetic gene cluster involved in the assembly of cylindrocyclophane F. Through a combination of in vitro enzyme characterization and feeding studies, we confirm the connection between this gene cluster and cylindrocyclophane production, elucidate the chemical events involved in initiating and terminating an unusual type I polyketide synthase assembly line, and discover that macrocycle assembly involves functionalization of an unactivated carbon center.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja308318p