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Promising anti-TB compound finally can be synthesized with ease

BUFFALO, N.Y. -- An efficient new strategy for synthesizing a natural marine product, which shows promising anti-tuberculosis activity but cannot be efficiently synthesized using conventional chemistry, is being reported by University at Buffalo organic chemists online on Feb. 10 in Angewandte Chemie International Edition.

The UB researchers' method synthesizes the compound in days rather than months, requires fewer steps and is capable of producing gram quantities.

The UB chemists describe the direct synthesis in the laboratory of the natural product isolated from the Pseudopterogorgia corals. They now are applying the synthesis method to other members of this class of compounds called diterpenes, some of which also have activity against TB and are potential anti-inflammatory and anticancer agents.

"We're poised now to make them all and to develop new analogs as potential medications," said Huw Davies, Ph.D., Larkin Professor of Organic Chemistry at UB and co-author.

Once thought to be nearly eliminated, tuberculosis is again among the world's most-deadly infectious diseases, killing between 2 million and 3 million people each year.

Its reemergence has been triggered partly by AIDS, which makes an individual 30 times more likely to develop TB, and by multidrug resistance caused by difficulties in getting patients to comply with long treatment regimens.

Davies explained that the family of marine compounds called diterpenes was discovered and demonstrated to have anti-TB activity in 2000, but as with most natural products, so little could be extracted from the marine organism that full biological evaluation was not possible.

To circumvent the problem, chemists have concentrated their efforts on producing the compounds in the laboratory.

Davies explained that the compounds have proven remarkably difficult to synthesize not because they're so complex, but because
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Contact: Ellen Goldbaum
goldbaum@buffalo.edu
716-645-5000 x1415
University at Buffalo
10-Feb-2005


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