3 years ago

Improved Synthesis for Modular Ascarosides Uncovers Biological Activity

Improved Synthesis for Modular Ascarosides Uncovers Biological Activity
Marco A. Sanchez-Ayala, Frank C. Schroeder, Paul W. Sternberg, Ying K. Zhang, Jagan Srinivasan
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01009

DOI: 10.1021/acs.orglett.7b01009

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