Biological Investigations of (+)-DanicalipinA Enabled Through Synthesis

被引：31

作者：

Bailey, Adrian M. ^{[1
]}

Wolfrum, Susanne ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 02期

关键词：

biological function; cell membranes; chlorosulfolipids; natural products; total synthesis; CHRYSOPHYTE POTERIOOCHROMONAS-MALHAMENSIS; OCHROMONAS-DANICA; ENANTIOSELECTIVE SYNTHESIS; ABSOLUTE-CONFIGURATION; FLAGELLAR MEMBRANE; OLEFIN METATHESIS; ADRIATIC MUSSELS; CHIRAL ALDEHYDES; ALLYLIC ALCOHOLS; IN-VITRO;

D O I：

10.1002/anie.201509082

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 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 Is 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 (+)-danicalipinA 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.

引用

页码：639 / 643

页数：5

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