A Stable Bis-Allyloxycarbonyl Biotin Aldehyde Derivative for Biotinylation Via Reductive Alkylation: Application to the Synthesis of a Biotinylated Doxorubicin Derivative

摘要

A novel, stable, biotion aldehyde derivative is reported in which the biotin moiety is N1, N3-protected by the allyloxycarbonyl group. The derivative is stable to sodium cyanoborohydride mediated reductive alkylation and is cleaved under mild Pd [0] catalysis. This novel biotin aldehyde should have wide application in avidin- and streptavidin-based detection systems and bioassays. The derivative is utilized in the synthesis of a biotinylated doxorubicin analogue that retains topoisomerase activity.