Structure Elucidation of the First Sex‐Inducing Pheromone of a Diatom

Diatoms are abundant unicellular microalgae, responsible for ≈20 % of global photosynthetic CO 2 fixation. Nevertheless, we know little about fundamental aspects of their biology, such as their sexual reproduction. Pheromone‐mediated chemical communication is crucial for successful mating. An attrac...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-10, Vol.62 (43), p.e202307165-e202307165
Main Authors: Klapper, Franziska A., Kiel, Christine, Bellstedt, Peter, Vyverman, Wim, Pohnert, Georg
Format: Article
Language:English
Subjects:
Attraction
Carbon dioxide
Carbon dioxide fixation
Cell cycle
Chemical communication
Hydroxyproline
Marine microorganisms
Mating behavior
Metabolites
Metabolomics
Negative ions
NMR
Nuclear magnetic resonance
Pheromones
Priming
Sex
Sexual behavior
Sexual reproduction
Synchronism
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Summary:Diatoms are abundant unicellular microalgae, responsible for ≈20 % of global photosynthetic CO 2 fixation. Nevertheless, we know little about fundamental aspects of their biology, such as their sexual reproduction. Pheromone‐mediated chemical communication is crucial for successful mating. An attraction pheromone was identified in the diatom Seminavis robusta , but metabolites priming cells for sex and synchronizing search and mating behavior remained elusive. These sex‐inducing pheromones (SIP) induce cell cycle arrest and trigger the production of the attraction pheromone. Here we describe the challenging structure elucidation of an S. robusta SIP. Guided by metabolomics, a candidate metabolite was identified and elucidated by labeling experiments, NMR, ESI MS n analyses, and chemical transformations. The use of negative ion mode MS was essential to decipher the unprecedented hydroxyproline and β‐sulfated aspartate‐containing cyclic heptapeptide that acts in femtomolar concentrations.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202307165