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

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

doi:10.1039/C5CC06988B

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

Agnieszka J. Szwalbe, Katherine Williams, Daniel E O'Flynn, Andy M Bailey, Nicholas P. Mulholland, Jason L. Vincent, Chris L Willis, Russell J Cox^*, Thomas J Simpson

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

32 Citations (Scopus)

468 Downloads (Pure)

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.

Original language	English
Pages (from-to)	17088-17091
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	96
Early online date	2 Oct 2015
DOIs	https://doi.org/10.1039/C5CC06988B
Publication status	Published - 14 Dec 2015

Research Groups and Themes

BCS and TECS CDTs
Bristol BioDesign Institute
Organic & Biological

Keywords

synthetic biology

Access to Document

10.1039/C5CC06988B

Full-text PDF (final published version)
This is the final published version of the article (version of record). It first appeared online via RSC at http://pubs.rsc.org/en/Content/ArticleLanding/2015/CC/C5CC06988B. Please refer to any applicable terms of use of the publisher.
Final published version, 1.47 MBLicence: CC BY
Supplementary Information PDF
This is the final published version of the article (version of record). It first appeared online via RSC at http://pubs.rsc.org/en/Content/ArticleLanding/2015/CC/C5CC06988B. Please refer to any applicable terms of use of the publisher.
Final published version, 1.04 MBLicence: CC BY

Handle.net

Persistent link

Cite this

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

@article{a2eefd35eabd4523a37f44f0dc43185e,

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.",

keywords = "synthetic biology",

author = "Szwalbe, \{Agnieszka J.\} and Katherine Williams and O'Flynn, \{Daniel E\} and Bailey, \{Andy M\} and Mulholland, \{Nicholas P.\} and Vincent, \{Jason L.\} and Willis, \{Chris L\} and Cox, \{Russell J\} and Simpson, \{Thomas J\}",

year = "2015",

month = dec,

day = "14",

doi = "10.1039/C5CC06988B",

language = "English",

volume = "51",

pages = "17088--17091",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "96",

}

Szwalbe, AJ, Williams, K, O'Flynn, DE, Bailey, AM, Mulholland, NP, Vincent, JL, Willis, CL, Cox, RJ & Simpson, TJ 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, vol. 51, no. 96, pp. 17088-17091. https://doi.org/10.1039/C5CC06988B

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, Vol. 51, No. 96, 14.12.2015, p. 17088-17091.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 – an insight into the biosynthesis of maleidrides

AU - Szwalbe, Agnieszka J.

AU - Williams, Katherine

AU - O'Flynn, Daniel E

AU - Bailey, Andy M

AU - Mulholland, Nicholas P.

AU - Vincent, Jason L.

AU - Willis, Chris L

AU - Cox, Russell J

AU - Simpson, Thomas J

PY - 2015/12/14

Y1 - 2015/12/14

N2 - 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.

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.

KW - synthetic biology

UR - https://www.scopus.com/pages/publications/84947998698

U2 - 10.1039/C5CC06988B

DO - 10.1039/C5CC06988B

M3 - Article (Academic Journal)

C2 - 26452099

AN - SCOPUS:84947998698

SN - 1359-7345

VL - 51

SP - 17088

EP - 17091

JO - Chemical Communications

JF - Chemical Communications

IS - 96

ER -

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

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Understanding Programming in Highly Reducing Iterative Fungal Polyketide Synthases - a Structural and Mechanistic Approach

Dr Andy M Bailey

Cite this

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

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Understanding Programming in Highly Reducing Iterative Fungal Polyketide Synthases - a Structural and Mechanistic Approach

Profiles

Dr Andy M Bailey

Cite this