Structure elucidation of the first sex-inducing pheromone of a diatom
Klapper, F.A.; Kiel, C.; Bellstedt, P.; Vyverman, W.; Pohnert, G. (2023). Structure elucidation of the first sex-inducing pheromone of a diatom. Angew. Chem. 62(43): e202307165. https://dx.doi.org/10.1002/anie.202307165
In: Angewandte Chemie. Wiley: Weinheim. ISSN 1433-7851; e-ISSN 1521-3773
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| Keywords |
Bacillariophyceae [WoRMS]; Seminavis robusta D.B.Danielidis & D.G.Mann, 2002 [WoRMS]
Marine/Coastal |
| Author keywords |
Cell Cycle Arrest; Diatoms; Marine Biofilms; Peptide Sex Pheromone; Structure Elucidation |
| Authors | | Top |
- Klapper, F.A.
- Kiel, C.
- Bellstedt, P.
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- Vyverman, W., more
- Pohnert, G.
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| Abstract |
Diatoms are abundant unicellular microalgae, responsible for ≈20 % of global photosynthetic CO2 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 MSn 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.
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