Synthetic diversification of natural products: semi-synthesis and evaluation of triazole jadomycins

Growth of Streptomyces venezuelae ISP5230 with O-propargyl-L-serine led to the efficient production of an alkyne-containing jadomycin. The installed alkyne functionality provided a uniquely reactive handle within the natural product and was subsequently reacted with a series of azides to afford an eight-member library of jadomycin triazoles. The compounds were evaluated for their DNA cleavage, antibacterial and cytotoxic properties.