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Improved Synthesis for Modular Ascarosides Uncovers Biological Activity.

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-?-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.

SUBMITTER: Zhang YK

PROVIDER: S-EPMC5533076 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Improved Synthesis for Modular Ascarosides Uncovers Biological Activity.

Zhang Ying K YK Sanchez-Ayala Marco A MA Sternberg Paul W PW Srinivasan Jagan J Schroeder Frank C FC

Organic letters 20170517 11

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 avoida ...[more]

PMID: 28513161

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