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Issue 26, 2020
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Modular and scalable synthesis of nematode pheromone ascarosides: implications in eliciting plant defense response

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Abstract

A highly efficient and modular synthesis of nematode pheromone ascarosides was developed, which highlights a 4-step scalable synthesis of the common intermediate 10 in 23% yield from commercially available L-rhamnose by using orthoesterification/benzylation/orthoester rearrangement as the key step. Six diverse ascarosides were synthesized accordingly. Notably, biological investigations revealed that ascr#1 and ascr#18 treatment resulted in enhanced callose accumulation in Arabidopsis leaves. And ascr#18 also increased the expression of defense-related genes such as PR1, PDF1.2, LOX2 and AOS, which might contribute to the enhanced plant defense responses. This study not only allows a facile access to 1-O, 2-O, and 4-O substituted ascarosides, but also provides valuable insights into their biological activities in inducing plant defense response, as well as their mode of action.

Graphical abstract: Modular and scalable synthesis of nematode pheromone ascarosides: implications in eliciting plant defense response

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Supplementary files

Article information


Submitted
28 Mar 2020
Accepted
16 Jun 2020
First published
17 Jun 2020

Org. Biomol. Chem., 2020,18, 4956-4961
Article type
Paper

Modular and scalable synthesis of nematode pheromone ascarosides: implications in eliciting plant defense response

S. Ning, L. Zhang, J. Ma, L. Chen, G. Zeng, C. Yang, Y. Zhou, X. Guo and X. Deng, Org. Biomol. Chem., 2020, 18, 4956
DOI: 10.1039/D0OB00652A

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