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At Last, An Azinomycin
PAMELA ZURER
The azinomycins--complex molecules produced by soil bacteria--are so unstable that little is known about their chemistry or biological activity. But studies done shortly after the family of compounds was first isolated in 1986 indicated that they possess antitumor activity. That was enough to lure chemists to try to synthesize the fragile molecules.
Chemistry professor Robert S. Coleman and coworkers at Ohio State University have now achieved the first total synthesis of azinomycin A [Angew. Chem. Int. Ed., 40, 1736 (2001)]. The researchers used a modular approach, trying various convergent routes until they finally succeeded.
"When I first saw the structure, I found it hard to believe so many reactive groups could be packed so densely into such a small area," Coleman says. "The more components you introduce, the more difficult each subsequent transformation gets."
Coleman's group hopes to create stable analogs and is investigating how the azinomycins bind covalently to DNA.
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