Thiarubrine A antiviral antifungal ( Candida albicans ) - - PowerPoint PPT Presentation

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Naturally occurring alkynes (+)-Laurencin isolated from red algae Laurencia glandulifera Burton, J.W.; Clark, J.S.; Derrer, S.; Stork, TC.; Bendall, J.G.; Holmes, AB.; J. Am. Chem. Soc. 1997 , 119 , 7483. Thiarubrine A antiviral

SLIDE 1

Naturally occurring alkynes

(+)-Laurencin isolated from red algae Laurencia glandulifera Burton, J.W.; Clark, J.S.; Derrer, S.; Stork, TC.; Bendall, J.G.; Holmes, AB.; J. Am. Chem. Soc. 1997, 119, 7483.

SLIDE 2

Thiarubrine A antiviral antifungal (Candida albicans) antibacterial Masato Koreeda, M.; Yang, W. J. Am. Chem. Soc. 1994, 116, 10793.

SLIDE 3

Enediynes

Share a common (Z)-1,5-diyn-3-ene moiety
Target minor groove or AT-rich DNA & intercalate
“Triggered” by an extended conjugate addition
Result of pulling trigger is a diradical
Diradical leads to SS and DS DNA cuts

Thiarubrine A antiviral antifungal ( Candida albicans ) - - PowerPoint PPT Presentation

Naturally occurring alkynes

(+)-Laurencin isolated from red algae Laurencia glandulifera Burton, J.W.; Clark, J.S.; Derrer, S.; Stork, TC.; Bendall, J.G.; Holmes, AB.; J. Am. Chem. Soc. 1997, 119, 7483.

Thiarubrine A antiviral antifungal (Candida albicans) antibacterial Masato Koreeda, M.; Yang, W. J. Am. Chem. Soc. 1994, 116, 10793.

Enediynes

NCZ diradical

Nicolaou, K.C.; Dai, W.-M. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1530.