Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy
| Autor: | Manuel G. Ricardo, Bernhard Westermann, Markus Schwark, Dayma Llanes, Timo H. J. Niedermeyer |
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| Rok vydání: | 2021 |
| Předmět: |
Coronavirus disease 2019 (COVID-19)
natural products Eagles Metabolite Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) Neurotoxins Catalysis chemistry.chemical_compound Central Nervous System Diseases Animals Neurotoxin Neurologic disease total synthesis Myelin Sheath Myelinopathy biindole-coupling Natural product Bird Diseases Communication Organic Chemistry Total synthesis bromination General Chemistry Communications indole chemistry Biochemistry |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | Aetokthonotoxin has recently been identified as the cyanobacterial neurotoxin causing Vacuolar Myelinopathy, a fatal neurologic disease, spreading through a trophic cascade and affecting birds of prey such as the bald eagle in the USA. Here, we describe the total synthesis of this specialized metabolite. The complex, highly brominated 1,2’‐biindole could be synthesized via a Somei‐type Michael reaction as key step. The optimised sequence yielded the natural product in five steps with an overall yield of 29 %. Heterocyclic chemistry: Synthesizing the eagle murder's weapon. With the identification of the alkaloid Aetokthonotoxin (AETX) as the neurotoxin causing wildlife deaths in the USA, further studies to characterize the biological effects of this natural product are mandatory. These studies will be enabled by a total synthesis of this natural product, which has been achieved in only five steps overall. |
| Databáze: | OpenAIRE |
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