Abstract
AbstractA total synthesis of the chlorosulfolipid (+)‐danicalipin A has been accomplished in 12 steps and 4.4 % overall yield. The efficient and scalable synthesis enabled in‐depth investigations of the lipid’s biological properties, in particular cytotoxicity towards various mammalian cell lines. Furthermore, the ability of (+)‐danicalipin A to increase the uptake of fluorophores into bacteria and mammalian cells was demonstrated, indicating it may enhance membrane permeability. By comparing (+)‐danicalipin A with racemic 1,14‐docosane disulfate, and the diol precursor of (+)‐danicalipin A, we have shown that both chlorine and sulfate functionalities are necessary for biological activity.
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