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5-Deoxyadenosine Salvage by Promiscuous Enzyme Activity leads to Bioactive Deoxy-Sugar Synthesis in Synechococcus elongatus

View ORCID ProfileJohanna Rapp, Pascal Rath, Joachim Kilian, View ORCID ProfileKlaus Brilisauer, View ORCID ProfileStephanie Grond, View ORCID ProfileKarl Forchhammer
doi: https://doi.org/10.1101/2020.12.30.424818
Johanna Rapp
aInterfaculty Institute of Microbiology and Infection Medicine, Microbiology/Organismic Interactions, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany
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  • ORCID record for Johanna Rapp
Pascal Rath
bInstitute of Organic Chemistry, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
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Joachim Kilian
cCenter for Plant Molecular Biology, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 32, 72076 Tübingen, Germany
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Klaus Brilisauer
aInterfaculty Institute of Microbiology and Infection Medicine, Microbiology/Organismic Interactions, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany
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Stephanie Grond
bInstitute of Organic Chemistry, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
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Karl Forchhammer
aInterfaculty Institute of Microbiology and Infection Medicine, Microbiology/Organismic Interactions, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 28, 72076 Tübingen, Germany
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  • For correspondence: karl.forchhammer@uni-tuebingen.de
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Abstract

7-Deoxysedoheptulose is an unusual deoxy-sugar, which acts as antimetabolite of the shikimate pathway thereby exhibiting antimicrobial and herbicidal activity. It is produced by the unicellular cyanobacterium Synechococcus elongatus PCC 7942, which has a small, stream-lined genome, assumed to be free from gene clusters for secondary metabolite synthesis. In this study, we identified the pathway for the synthesis of 7-deoxysedoheptulose. It originates from 5-deoxyadenosine, a toxic byproduct of radical S-adenosylmethionine (SAM) enzymes, present in all domains of life. Thereby we identified a novel 5-deoxyadenosine salvage pathway, which first leads to the synthesis and excretion of 5-deoxyribose and subsequently of 7-deoxysedoheptulose. Remarkably, all reaction steps are conducted by promiscuous enzymes. This is a unique example for the synthesis of a bioactive compound without involving a specific gene cluster. This challenges the view on bioactive molecule synthesis by extending the range of possible compounds beyond the options predicted from secondary metabolite gene clusters.

Competing Interest Statement

The authors have declared no competing interest.

  • Abbreviations

    SAM
    S-Adenosylmethionine
    MTA
    Methylthioadenosine
    5dAdo
    5-Deoxyadenosine
    MSP
    Methionine salvage pathway
    5dR
    5-Deoxyribose
    7dSh
    7-Deoxysedoheptulose
    5dR-1P
    5-Deoxyribose 1-phosphate
    5dRu-1P
    5-Deoxyribulose 1-phosphate
    MTRI
    Methylthioribose 1-phosphate isomerase
    MTR
    Methylthioribose
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    Posted December 31, 2020.
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    5-Deoxyadenosine Salvage by Promiscuous Enzyme Activity leads to Bioactive Deoxy-Sugar Synthesis in Synechococcus elongatus
    Johanna Rapp, Pascal Rath, Joachim Kilian, Klaus Brilisauer, Stephanie Grond, Karl Forchhammer
    bioRxiv 2020.12.30.424818; doi: https://doi.org/10.1101/2020.12.30.424818
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    5-Deoxyadenosine Salvage by Promiscuous Enzyme Activity leads to Bioactive Deoxy-Sugar Synthesis in Synechococcus elongatus
    Johanna Rapp, Pascal Rath, Joachim Kilian, Klaus Brilisauer, Stephanie Grond, Karl Forchhammer
    bioRxiv 2020.12.30.424818; doi: https://doi.org/10.1101/2020.12.30.424818

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