PubAg

Main content area

Improved Synthesis for Modular Ascarosides Uncovers Biological Activity

Author:
Zhang, Ying K., Sanchez-Ayala, Marco A., Sternberg, Paul W., Srinivasan, Jagan, Schroeder, Frank C.
Source:
Organic letters 2017 v.19 no.11 pp. 2837-2840
ISSN:
1523-7052
Subject:
Caenorhabditis elegans, bioactive properties, bioassays, chemical reactions, chemical structure, organic compounds, sugars, sulfates
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.
Agid:
5792924