Boyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University , Ithaca, New York 14853, United States.
Howard Hughes Medical Institute and Division of Biology, California Institute of Technology , Pasadena, California 91125, United States.
Org Lett. 2017 Jun 2;19(11):2837-2840. doi: 10.1021/acs.orglett.7b01009. Epub 2017 May 17.
A versatile synthesis of modular ascarosides, a family of signaling molecules from Caenorhabditis elegans and other nematodes, via hydrogenolysis of a cyclic sulfate derived from methyl-α-l-rhamnopyranoside is reported. The route enables selective introduction of different side chains at the 1, 2, and 4 positions of the sugar, as demonstrated for ascarosides from C. elegans and Pristionchus pacificus. Bioassays with synthetic samples of 4'-tigloyl ascaroside mbas#3 revealed its role as an avoidance or dispersal signal.
本文报道了一种通过氢化衍生自甲基-α-l-鼠李吡喃糖苷的环状硫酸盐，从而实现模块化ascarosides（一种来自秀丽隐杆线虫和其他线虫的信号分子家族）的多功能合成。该路线能够在糖的 1、2 和 4 位选择性地引入不同的侧链，如来自秀丽隐杆线虫和太平洋色矛线虫的ascarosides 所示。对合成的 4'-tigloyl ascaroside mbas#3 的生物测定表明，它作为一种回避或扩散信号的作用。
