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Scripps research team achieves critical step to opening elusive class of compounds to drug discovery
Date:11/6/2011

et compound. Creating each increasingly complex molecule along that line is an inefficient process that often requires numerous extra steps to prevent unwanted reactions or to correct other chemical complications. "It's like trying to convert a Toyota Corolla into a Ferrari instead of just building a Ferrari," said Baran.

To build the Ferrari, Baran and his team are taking a different route. In 2009, the researchers showed that by using an unconventional scheme they could produce a simpler relative of Taxol called eudesmane. They analyzed this target and then created what Baran calls a retrosynthesis pyramid. This is a diagram with the target compound at the top and lower levels filled with molecules that could theoretically be modified to reach the level above them. Such a pyramid reveals not a set linear path, but a variety of path options open to chemical exploration.

With taxanes and related compounds there are two main phases in production, the cyclase phase and oxidase phase. Working up the bottom half of the pyramid involves mostly well-understood chemistry. During this cyclase phase, researchers construct a chemical scaffolding that Baran likens to a Christmas tree to which ornaments must then be attached. The ornaments are primarily reactive oxygen molecules and this "decoration," or oxidation, phase is the most challenging.

The eudesmane synthesis was something like decorating the Charlie Brown Christmas tree, while a completed Taxol production could be compared to the lighting of the famous multi-story Rockefeller Center tree.

In the new paper, Baran's group reports erecting that Rockefeller tree and adding the first few ornaments -- a molecule called taxadiene. "It's a Herculean task," said Baran of Taxol synthesis, "What we're doing here is merely part one."

A conventional taxadiene synthesis is inefficient and involves 26 steps to produce. The Baran group's method involves just 10 steps to produce many
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Contact: Mika Ono
mikaono@scripps.edu
858-784-2052
Scripps Research Institute
Source:Eurekalert  

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