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Improved Synthesis for Modular Ascarosides Uncovers Biological Activity

Zhang, Ying K. and Sanchez-Ayala, Marco A. and Sternberg, Paul W. and Srinivasan, Jagan and Schroeder, Frank C. (2017) Improved Synthesis for Modular Ascarosides Uncovers Biological Activity. Organic Letters, 19 (11). pp. 2837-2840. ISSN 1523-7060. PMCID PMC5533076. https://resolver.caltech.edu/CaltechAUTHORS:20170518-101558193

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/acs.orglett.7b01009DOIArticle
http://pubs.acs.org/doi/full/10.1021/acs.orglett.7b01009PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b01009PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5533076PubMed CentralArticle
ORCID:
AuthorORCID
Sternberg, Paul W.0000-0002-7699-0173
Srinivasan, Jagan0000-0001-5449-7938
Schroeder, Frank C.0000-0002-4420-0237
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.
Funders:
Funding AgencyGrant Number
NIHGM113692
NIHGM088290
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
Issue or Number:11
PubMed Central ID:PMC5533076
Record Number:CaltechAUTHORS:20170518-101558193
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170518-101558193
Official Citation:Improved Synthesis for Modular Ascarosides Uncovers Biological Activity Ying K. Zhang, Marco A. Sanchez-Ayala, Paul W. Sternberg, Jagan Srinivasan, and Frank C. Schroeder Organic Letters 2017 19 (11), 2837-2840 DOI: 10.1021/acs.orglett.7b01009
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77564
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:18 May 2017 17:31
Last Modified:03 Oct 2019 17:59

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