Organic Letters
Organic Letters
4 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

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.