New insights into polyene macrolide biosynthesis in Couchioplanes caeruleus

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Title: New insights into polyene macrolide biosynthesis in Couchioplanes caeruleus
Authors: Sheehan, James
Murphy, Cormac D.
Caffrey, Patrick
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Date: 1-May-2017
Abstract: Couchioplanes caeruleus DSM43634 synthesises 67–121C, an aromatic heptaene macrolide that contains a mannosyl-mycosaminyl disaccharide. An improved draft genome sequence was used to obtain the biosynthetic gene cluster for this antifungal. Bioinformatic analysis of the polyketide synthase indicated that extension modules 7 and 8 contain A-type ketoreductase and dehydratase domains. These modules are therefore predicted to form cis double bonds. The deduced stereostructure of the 67–121C macrolactone is identical to that experimentally determined for the partricin subgroup of aromatic heptaenes. Some of these polyenes are N-methylated on the aminoacetophenone moiety. The C. caeruleus AceS protein was shown to methylate 4-aminoacetophenone and esters of 4-aminobenzoate, but not 4-aminobenzoate. This suggests that the substrate specificity of AceS prevents it from interfering with folate biosynthesis. The methyltransferase should be valuable for chemoenzymatic alkylation of compounds that contain aminobenzoyl moieties.
Funding Details: Science Foundation Ireland
University College Dublin
Type of material: Journal Article
Publisher: Royal Society of Chemistry
Journal: Molecular BioSystems
Volume: 13
Issue: 5
Start page: 866
End page: 873
Copyright (published version): 2017 The Royal Society of Chemistry
Keywords: Polyene macrolidesCouchioplanes caeruleus
DOI: 10.1039/c7mb00112f
Language: en
Status of Item: Peer reviewed 2018-03-31T01:00:14Z
Appears in Collections:Biomolecular and Biomedical Science Research Collection

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