Heronamides A-C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp A biosynthetic case for synchronized tandem electrocyclization

Raju, Ritesh, Piggott, Andrew M., Conte, Melissa M. and Capon, Robert J. (2010) Heronamides A-C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp A biosynthetic case for synchronized tandem electrocyclization. Organic & Biomolecular Chemistry, 8 20: 4682-4689. doi:10.1039/c0ob00267d


Author Raju, Ritesh
Piggott, Andrew M.
Conte, Melissa M.
Capon, Robert J.
Title Heronamides A-C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp A biosynthetic case for synchronized tandem electrocyclization
Journal name Organic & Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2010-10-01
Year available 2011
Sub-type Article (original research)
DOI 10.1039/c0ob00267d
Open Access Status Not Open Access
Volume 8
Issue 20
Start page 4682
End page 4689
Total pages 8
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2011
Language eng
Formatted abstract
A Streptomyces sp. isolated from a shallow water sediment sample collected off Heron Island,
Australia, afforded three new polyketide macrolactams, heronamides A–C (1–3). Structures were assigned to the heronamides on the basis of detailed spectroscopic analysis, chemical derivatization and biosynthetic considerations. A plausible biosynthetic pathway is proposed in which key carbocyclic ring transformations proceed via an unprecedented synchronized tandem electrocyclization. This biosynthesis provides a framework for the assignment of complete relative configurations across all heronamides, and inspires an attractive biomimetic strategy for future total syntheses. Heronamide C elicits a dramatic and reversible non-cytotoxic effect on mammalian cell morphology.
© The Royal Society of Chemistry 2010
Keyword Macrocyclic Lactam
Actinomycete
Vicenistatin
Elucidation
Cyclamenol
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Received 16th June 2010, Accepted 22nd July 2010

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
Institute for Molecular Bioscience - Publications
 
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Created: Sun, 17 Oct 2010, 10:04:27 EST