What molecule am I?
(R)-Dysidazirine is a natural product that Tadeusz F. Molinski and Chris M. Ireland* at the University of Utah (Salt Lake City) discovered in 1988 in the marine sponge Dysidea fragilis. The 2H-azirine ring occurs in nature only in D. fragilis, congeners from a different sponge, and azirinomycin1, an antibiotic that researchers at Merck (Rahway, NJ) obtained in 1970 by culturing the bacterium Streptomyces aureus.
Remarkably, despite its exceptionally high ring strain, the α,β-unsaturated 2H-azirine ring is stable in the absence of nucleophiles. The 1H NMR spectrum of a sample stored at –20 °C for 12 years remained unchanged, but the molecule had partially racemized.
Franklin Davis*, G. Venkat Reddy, and Hu Liu at Temple University (Philadelphia) reported the synthesis of optically pure (R)-dysidazirine in 1995. The data for the synthetic compound and natural product perfectly matched. except for the specific rotation. Apparently, the natural (R)-dysidazirine was only 89% optically pure.
Dysidazirine exhibits potent in vitro antifungal activity against the pathogenic yeast Candida albicans. It also inhibits cultured HCT-116 human colon cancer cells.
No hazard information on (R)-dysidazirine is available.
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