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Issue 9, 2014
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Uncovering the origin of Z-configured double bonds in polyketides: intermediate E-double bond formation during borrelidin biosynthesis

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Abstract

Formation of Z-configured double bonds in reduced polyketides is uncommon and their origins have not been extensively studied. To investigate the origin of the Z-configured double bond in the macrolide borrelidin, the recombinant dehydratase domains BorDH2 and BorDH3 were assayed with a synthetic analogue of the predicted tetraketide substrate. The configuration of the dehydrated products was determined to be E in both cases by comparison to synthetic standards. Detailed NMR spectroscopic analysis of the biosynthetic intermediate pre-borrelidin confirmed the E,E-configuration of the full-length polyketide synthase product. In contrast to a previously-proposed hypothesis, our results show that in this case the Z-configured double bond is not formed via dehydration from a 3 L-configured precursor, but rather as the result of a later isomerization process.

Graphical abstract: Uncovering the origin of Z-configured double bonds in polyketides: intermediate E-double bond formation during borrelidin biosynthesis

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Publication details

The article was received on 25 Mar 2014, accepted on 17 Jun 2014 and first published on 30 Jun 2014


Article type: Edge Article
DOI: 10.1039/C4SC00883A
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Citation: Chem. Sci., 2014,5, 3563-3567

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    Uncovering the origin of Z-configured double bonds in polyketides: intermediate E-double bond formation during borrelidin biosynthesis

    N. Kandziora, J. N. Andexer, S. J. Moss, B. Wilkinson, P. F. Leadlay and F. Hahn, Chem. Sci., 2014, 5, 3563
    DOI: 10.1039/C4SC00883A

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