Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii

Hang Li; Cameron L.M. Gilchrist; Heather J. Lacey; Andrew Crombie; Daniel Vuong; John I. Pitt; Ernest Lacey; Yit Heng Chooi; Andrew M. Piggott

doi:10.1021/acs.orglett.8b04042

Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii

Hang Li, Cameron L.M. Gilchrist, Heather J. Lacey, Andrew Crombie, Daniel Vuong, John I. Pitt, Ernest Lacey, Yit Heng Chooi, Andrew M. Piggott

School of Molecular Sciences

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37 Citations (Scopus)

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Abstract

The burnettramic acids are a new class of antibiotics from an Australian fungus Aspergillus burnettii. The rare bolaamphiphilic scaffold consists of β-d-mannose linked to a pyrrolizidinedione unit via a 26-carbon chain. The most abundant metabolite displayed potent in vitro antifungal activity. Comparative genomics identified the hybrid PKS-NRPS bua gene cluster, which was verified by heterologous pathway reconstitution in Aspergillus nidulans.

Original language	English
Pages (from-to)	1287-1291
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.8b04042
Publication status	Published - 1 Mar 2019

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10.1021/acs.orglett.8b04042

Li et al., 2019 Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettiiAccepted author manuscript, 5.38 MB

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Li, H., Gilchrist, C. L. M., Lacey, H. J., Crombie, A., Vuong, D., Pitt, J. I., Lacey, E., Chooi, Y. H., & Piggott, A. M. (2019). Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii. Organic Letters, 21(5), 1287-1291. https://doi.org/10.1021/acs.orglett.8b04042

@article{10dedd2f56e7448a8ec4842252142a9c,

title = "Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii",

abstract = "The burnettramic acids are a new class of antibiotics from an Australian fungus Aspergillus burnettii. The rare bolaamphiphilic scaffold consists of β-d-mannose linked to a pyrrolizidinedione unit via a 26-carbon chain. The most abundant metabolite displayed potent in vitro antifungal activity. Comparative genomics identified the hybrid PKS-NRPS bua gene cluster, which was verified by heterologous pathway reconstitution in Aspergillus nidulans.",

author = "Hang Li and Gilchrist, {Cameron L.M.} and Lacey, {Heather J.} and Andrew Crombie and Daniel Vuong and Pitt, {John I.} and Ernest Lacey and Chooi, {Yit Heng} and Piggott, {Andrew M.}",

year = "2019",

month = mar,

day = "1",

doi = "10.1021/acs.orglett.8b04042",

language = "English",

volume = "21",

pages = "1287--1291",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "Rubber Division of the American Chemical Society",

number = "5",

}

Li, H, Gilchrist, CLM, Lacey, HJ, Crombie, A, Vuong, D, Pitt, JI, Lacey, E, Chooi, YH & Piggott, AM 2019, 'Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii', Organic Letters, vol. 21, no. 5, pp. 1287-1291. https://doi.org/10.1021/acs.orglett.8b04042

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AU - Li, Hang

AU - Gilchrist, Cameron L.M.

AU - Lacey, Heather J.

AU - Crombie, Andrew

AU - Vuong, Daniel

AU - Pitt, John I.

AU - Lacey, Ernest

AU - Chooi, Yit Heng

AU - Piggott, Andrew M.

PY - 2019/3/1

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N2 - The burnettramic acids are a new class of antibiotics from an Australian fungus Aspergillus burnettii. The rare bolaamphiphilic scaffold consists of β-d-mannose linked to a pyrrolizidinedione unit via a 26-carbon chain. The most abundant metabolite displayed potent in vitro antifungal activity. Comparative genomics identified the hybrid PKS-NRPS bua gene cluster, which was verified by heterologous pathway reconstitution in Aspergillus nidulans.

AB - The burnettramic acids are a new class of antibiotics from an Australian fungus Aspergillus burnettii. The rare bolaamphiphilic scaffold consists of β-d-mannose linked to a pyrrolizidinedione unit via a 26-carbon chain. The most abundant metabolite displayed potent in vitro antifungal activity. Comparative genomics identified the hybrid PKS-NRPS bua gene cluster, which was verified by heterologous pathway reconstitution in Aspergillus nidulans.

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JO - Organic Letters

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SN - 1523-7052

IS - 5

ER -

Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii

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Uncovering the Hidden Secondary Metabolite Biosynthetic Potential of Fungi

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Discovery and Heterologous Biosynthesis of the Burnettramic Acids: Rare PKS-NRPS-Derived Bolaamphiphilic Pyrrolizidinediones from an Australian Fungus, Aspergillus burnettii

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Uncovering the Hidden Secondary Metabolite Biosynthetic Potential of Fungi

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