Improved Synthesis for Modular Ascarosides Uncovers Biological Activity

Organic Letters
Ying K ZhangFrank C Schroeder

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.

References

Jun 15, 2007·Nature Chemical Biology·Rebecca A ButcherJon Clardy
Apr 4, 2009·European Journal of Medicinal Chemistry·Mankil JungMiyeon Oh
Apr 7, 2009·Proceedings of the National Academy of Sciences of the United States of America·Chirag PungaliyaFrank C Schroeder
Jan 14, 2012·Journal of the American Chemical Society·Stephan H von ReussFrank C Schroeder
Nov 20, 2012·Angewandte Chemie·Neelanjan BoseFrank C Schroeder
Dec 19, 2012·Current Biology : CB·Yen-Ping HsuehPaul W Sternberg
Mar 20, 2013·Proceedings of the National Academy of Sciences of the United States of America·Andreas H LudewigFrank C Schroeder
May 22, 2013·The Journal of Biological Chemistry·Alexander B ArtyukhinFrank C Schroeder
Aug 8, 2013·Bioorganic & Medicinal Chemistry·Kyle A HollisterJustin R Ragains
Jun 11, 2015·Natural Product Reports·Stephan H von Reuss, Frank C Schroeder
Jul 24, 2015·Nature Communications·Patricia ManosalvaDaniel F Klessig
Oct 26, 2016·Current Biology : CB·Erin Z Aprison, Ilya Ruvinsky
Nov 4, 2016·Nature·Joshua S GreeneCornelia I Bargmann
Apr 4, 2017·Angewandte Chemie·Oishika PandaFrank C Schroeder

❮ Previous
Next ❯

Citations

Sep 25, 2019·Nature Ecology & Evolution·Daehan LeeErik C Andersen
Aug 20, 2020·Journal of Neurogenetics·YongJin CheonKyuhyung Kim
Mar 13, 2020·Proceedings of the National Academy of Sciences of the United States of America·Ching-Ting YangYen-Ping Hsueh

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

WormBook : the Online Review of C. Elegans Biology
Andre Pires-daSilva
WormBook : the Online Review of C. Elegans Biology
Andre Pires da Silva
Médecine sciences : M/S
Michel Labouesse
Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme
Y Sadaie, K Suzuki
© 2022 Meta ULC. All rights reserved