Phalloidin
chemical compound
Phalloidin belongs to a class of toxins called phallotoxins, which are found in mushrooms of the genus Amanita. It is a rigid bicyclic heptapeptide that is lethal after a few days when injected into the bloodstream. The major symptom of phalloidin poisoning is acute hunger due to the destruction of liver cells. It functions by binding and stabilizing filamentous actin (F-actin) and effectively prevents the depolymerization of actin fibers. Due to its tight and selective binding to F-actin, derivatives of phalloidin containing fluorescent tags are used widely in microscopy to visualize F-actin in biomedical research.
Discovery and background
Phalloidin was one of the first cyclic peptides to be discovered. It was isolated from the death cap mushroom and crystallized by Feodor Lynen and Ulrich Wieland in 1937. Its structure is unusual in that it contains a cysteine-tryptophan linkage to form a bicyclic heptapeptide. This linkage had not been characterized before and makes the structure elucidation of phalloidin significantly more difficult. They determined the presence of the sulfur atom using UV spectroscopy and found that this ring structure had a slightly shifted wavelength.
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This entry incorporates text from “Phalloidin” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.