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

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Agnieszka J. Szwalbe
  • Katherine Williams
  • Daniel E. O'Flynn
  • Andrew M. Bailey
  • Nicholas P. Mulholland
  • Jason L. Vincent
  • Christine L. Willis
  • Russell J. Cox
  • Thomas J. Simpson

Organisationseinheiten

Externe Organisationen

  • University of Bristol
  • Syngenta
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Details

OriginalspracheEnglisch
Seiten (von - bis)17088-17091
Seitenumfang4
FachzeitschriftChemical communications
Jahrgang51
Ausgabenummer96
PublikationsstatusVeröffentlicht - 1 Jan. 2015

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.

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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. / Szwalbe, Agnieszka J.; Williams, Katherine; O'Flynn, Daniel E. et al.
in: Chemical communications, Jahrgang 51, Nr. 96, 01.01.2015, S. 17088-17091.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Szwalbe, A. J., Williams, K., O'Flynn, D. E., Bailey, A. M., Mulholland, N. P., Vincent, J. L., Willis, C. L., Cox, R. J., & Simpson, T. J. (2015). Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021-an insight into the biosynthesis of maleidrides. Chemical communications, 51(96), 17088-17091. https://doi.org/10.1039/c5cc06988b
Szwalbe AJ, Williams K, O'Flynn DE, Bailey AM, Mulholland NP, Vincent JL et al. Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021-an insight into the biosynthesis of maleidrides. Chemical communications. 2015 Jan 1;51(96):17088-17091. doi: 10.1039/c5cc06988b
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title = "Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021-an insight into the biosynthesis of maleidrides",
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.",
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TY - JOUR

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AU - Szwalbe, Agnieszka J.

AU - Williams, Katherine

AU - O'Flynn, Daniel E.

AU - Bailey, Andrew M.

AU - Mulholland, Nicholas P.

AU - Vincent, Jason L.

AU - Willis, Christine L.

AU - Cox, Russell J.

AU - Simpson, Thomas J.

PY - 2015/1/1

Y1 - 2015/1/1

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AB - 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.

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DO - 10.1039/c5cc06988b

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