| Title: | Improved Synthesis for Modular Ascarosides Uncovers Biological Activity |
| Author(s): | Zhang YK; Sanchez-Ayala MA; Sternberg PW; Srinivasan J; Schroeder FC; |
| Address: | "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. Department of Biology and Biotechnology, Worcester Polytechnic Institute , Worcester, Massachusetts 01609, United States" |
| DOI: | 10.1021/acs.orglett.7b01009 |
| ISSN/ISBN: | 1523-7052 (Electronic) 1523-7060 (Print) 1523-7052 (Linking) |
| 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-alpha-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" |
| Keywords: | Animals Caenorhabditis elegans Glycolipids/*chemical synthesis Molecular Structure Pheromones; |
| Notes: | "MedlineZhang, Ying K Sanchez-Ayala, Marco A Sternberg, Paul W Srinivasan, Jagan Schroeder, Frank C eng R01 DC016058/DC/NIDCD NIH HHS/ R01 GM088290/GM/NIGMS NIH HHS/ R01 GM113692/GM/NIGMS NIH HHS/ HHMI/Howard Hughes Medical Institute/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't 2017/05/18 Org Lett. 2017 Jun 2; 19(11):2837-2840. doi: 10.1021/acs.orglett.7b01009. Epub 2017 May 17" |
