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Issue 96, 2015
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Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 – an insight into the biosynthesis of maleidrides

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Abstract

The filamentous fungus Byssochlamys fulva strain IMI 40021 produces (+)-byssochlamic acid 1, its novel dihydroanalogue 2 and four related secondary metabolites. Agnestadrides A, 17 and B, 18 constitute a novel class of seven-membered ring, maleic anhydride-containing (hence termed heptadride) natural products. The putative maleic anhydride precursor 5 for both nonadride and heptadride biosynthesis was isolated as a fermentation product for the first time and its structure confirmed by synthesis. Acid 5 undergoes facile decarboxylation to anhydride 6. The generic term maleidrides is proposed to encompass biosynthetically-related compounds containing maleic anhydride moieties fused to an alicyclic ring, varying in size and substituents.

Graphical abstract: Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 – an insight into the biosynthesis of maleidrides

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Publication details

The article was received on 19 Aug 2015, accepted on 02 Oct 2015 and first published on 02 Oct 2015


Article type: Communication
DOI: 10.1039/C5CC06988B
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Chem. Commun., 2015,51, 17088-17091
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    Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 – an insight into the biosynthesis of maleidrides

    A. J. Szwalbe, K. Williams, D. E. O'Flynn, A. M. Bailey, N. P. Mulholland, J. L. Vincent, C. L. Willis, R. J. Cox and T. J. Simpson, Chem. Commun., 2015, 51, 17088
    DOI: 10.1039/C5CC06988B

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