Cyanobacterial antimetabolite 7-deoxy-sedoheptulose blocks the shikimate pathway to inhibit the growth of prototrophic organisms

Klaus Brilisauer, Johanna Rapp, Pascal Rath, Anna Schöllhorn, Lisa Bleul, Elisabeth Weiß, Mark Stahl, Stephanie Grond () and Karl Forchhammer ()
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Klaus Brilisauer: Eberhard Karls Universität Tübingen
Johanna Rapp: Eberhard Karls Universität Tübingen
Pascal Rath: Eberhard Karls Universität Tübingen
Anna Schöllhorn: Eberhard Karls Universität Tübingen
Lisa Bleul: Eberhard Karls Universität Tübingen
Elisabeth Weiß: Eberhard Karls Universität Tübingen
Mark Stahl: Eberhard Karls Universität Tübingen
Stephanie Grond: Eberhard Karls Universität Tübingen
Karl Forchhammer: Eberhard Karls Universität Tübingen

Nature Communications, 2019, vol. 10, issue 1, 1-11

Abstract: Abstract Antimetabolites are small molecules that inhibit enzymes by mimicking physiological substrates. We report the discovery and structural elucidation of the antimetabolite 7-deoxy-sedoheptulose (7dSh). This unusual sugar inhibits the growth of various prototrophic organisms, including species of cyanobacteria, Saccharomyces, and Arabidopsis. We isolate bioactive 7dSh from culture supernatants of the cyanobacterium Synechococcus elongatus. A chemoenzymatic synthesis of 7dSh using S. elongatus transketolase as catalyst and 5-deoxy-d-ribose as substrate allows antimicrobial and herbicidal bioprofiling. Organisms treated with 7dSh accumulate 3-deoxy-d-arabino-heptulosonate 7-phosphate, which indicates that the molecular target is 3-dehydroquinate synthase, a key enzyme of the shikimate pathway, which is absent in humans and animals. The herbicidal activity of 7dSh is in the low micromolar range. No cytotoxic effects on mammalian cells have been observed. We propose that the in vivo inhibition of the shikimate pathway makes 7dSh a natural antimicrobial and herbicidal agent.

Date: 2019
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DOI: 10.1038/s41467-019-08476-8

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