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Synthesis

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February 26, 2018 | A version of this story appeared in Volume 96, Issue 9

 

Letters to the editor

Palytoxin

We read with interest Emma Hiolski’s article entitled “Palytoxin: The danger hidden in tropical aquariums” that described palytoxin as the Mount Everest of chemistry due to its remarkable chemical complexity (Jan. 8, page 12). As detailed, professor Kishi’s synthesis in the ’90s was in no doubt a tremendous accomplishment in assembling its structure, having a backbone of 115 carbon atoms!

What was overlooked by the author was an equally important history that is sadly often downplayed in the chemical literature in favor of chemical synthesis, and that has to do with the discovery and characterization of the natural product itself; palytoxin in this case during the ’70s and early ’80s. That work was led by the late Richard E. Moore of the University of Hawaii, who reported its structure and stereochemistry in two [Journal of the American Chemical Society] articles in 1981 and 1982 (DOI: 10.1021/ja00399a093 and DOI: 10.1021/ja00377a064). That work was the culmination of over a decade of research of incredible ingenuity at a time when chromatography, NMR, and other modern conveniences that we take for granted today were nonexistent or in their infancy. Additional discovery work by professor Daisuke Uemura from Shizuoka University at the time amplified the structure of palytoxin and its derivatives (Tetrahedron Lett. 1981, DOI: 10.1016/S0040-4039(01)90551-9). It was this collection of discovery work that made it possible for Kishi and others to finally assign a chemical structure to the name and fascinating history of palytoxin.

So let’s not forget about the incredible chemists who illuminate for us the chemical faces of nature’s molecules that continue to inspire us in many scientific disciplines.

Bradley Moore (son of Richard E. Moore)
La Jolla, Calif.

William Fenical
Del Mar, Calif.


Corrections:

Jan. 29, page 10: In the science brief on a possible technique to search for extraterrestrial life, the pair of gases given as the atmospheric disequilibrium on Earth was incorrect. They should be methane and oxygen.

Feb. 12, page 14: In a news story about NIGMS’s decision to stop funding a predoctoral fellowship, the number of fellowships should have been 85 since 2015, not per year. The NSF fellowships mentioned in the story are also available in the early years of graduate school, not just before students enter graduate school.

Feb. 19, page 20: In the feature story on vaccines against drugs of abuse, the reference for the oxycodone vaccine entry in the table is incorrect. It is PLOS One 2014, DOI: 10.1371/journal.pone.0096547.

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