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Synthesis and a Preliminary DNA Binding Study of Hybrids of the Carbohydrate Domain of Calicheamicin γ and the Aglycone of Daunorubicin: Calichearubicins A and B

1996; Wiley; Volume: 35; Issue: 23-24 Linguagem: Inglês

10.1002/anie.199627971

1521-3773

Kristopher M. Depew, Steven M. Zeman, Serge H. Boyer, Derek J. Denhart, Norihiro Ikemoto, Samuel J. Danishefsky, Donald M. Crothers,

Synthetic Organic Chemistry Methods

In calichearubicin B (1) the aglycon of daunorubicin and the carbohydrate domain of calicheamicin γ are linked by a spacer (calichearubicin A lacks this spacer). The aglycone serves as an anthracycline-like intercalator, while the carbohydrate portion binds to the minor groove of DNA. Thus calichearubicin B exhibits properties of both parent compounds.