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Scripps Research team wins global race to achieve landmark synthesis of perplexing natural product
Date:1/12/2010

LA JOLLA, CAJanuary 12, 2010In 1993 researchers discovered a chemical compound in a sponge off Palau, an island nation in the Pacific Ocean, that has shown anticancer, antibacterial, and antifungal pharmaceutical promise. But that wasn't its greatest allure, at least not for chemists.

This compound, called Palau'amine, is so chemically complex that finding a way to produce it in the laboratory became the most hotly pursued synthetic chemistry goal in modern history. Groups around the globe dedicated millions to the challenge, but it is a team of scientists from The Scripps Research Institute that has finally completed the quest.

Anonymous reviewers of the team's paper describing the achievement, which will be published as the cover article of an upcoming edition of the international journal Angewandte Chemie, called the work variously "a masterpiece," "spectacular," "a landmark," and "a spectacular synthetic achievement including unprecedented and previously 'unthinkable' transformations."

An Exquisite Target

Synthesizing Palau'amine is a daunting task because of two main features. First, it has a molecular framework with inner connections so bizarre that chemists have been taught in graduate school that they can't exist in nature. The most striking feature is a combination of two carbon rings sprinkled with nitrogen atoms that bond in a way that puts phenomenal strain on the molecule.

"It's so contorted that you wouldn't expect it to be possible," says Scripps Research chemist Phil Baran, Ph.D., who led the team that made the breakthrough.

To add to the fun, Palau'amine is exceedingly fragile. For instance it falls apart if exposed to the wrong pH level. All told, developing a synthesis method proved to be the chemical equivalent of a treasure hunt through booby-trapped terrain where one false move sends the quarry up in smoke.

Baran's lab had been working on the Palau'amine challenge
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Contact: Keith McKeown
kmckeown@scripps.edu
858-784-8134
Scripps Research Institute
Source:Eurekalert

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