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Published June 2, 2017 | Supplemental Material + Accepted Version
Journal Article Open

Improved Synthesis for Modular Ascarosides Uncovers Biological Activity

Abstract

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.

Additional Information

© 2017 American Chemical Society. Received: April 3, 2017; Published: May 17, 2017. This work was supported in part by the NIH (GM113692 and GM088290 to FCS) and the Howard Hughes Medical Institute. We thank Robert J. Micikas (University of Pennsylvania) for helpful comments and Alexander Artyukhin (Boyce Thompson Institute) for assistance with mass spectrometry.

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Accepted Version - nihms877819.pdf

Supplemental Material - ol7b01009_si_001.pdf

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