Literature DB >> 28513161

Improved Synthesis for Modular Ascarosides Uncovers Biological Activity.

Ying K Zhang1, Marco A Sanchez-Ayala1, Paul W Sternberg2, Jagan Srinivasan3, Frank C Schroeder1.   

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.

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Year:  2017        PMID： 28513161      PMCID： PMC5533076          DOI： 10.1021/acs.orglett.7b01009

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  25 in total

Review 1.  Combinatorial chemistry in nematodes: modular assembly of primary metabolism-derived building blocks.

Authors:  Stephan H von Reuss; Frank C Schroeder
Journal:  Nat Prod Rep       Date:  2015-07       Impact factor: 13.423

2.  Biosynthesis of Modular Ascarosides in C. elegans.

Authors:  Oishika Panda; Allison E Akagi; Alexander B Artyukhin; Joshua C Judkins; Henry H Le; Parag Mahanti; Sarah M Cohen; Paul W Sternberg; Frank C Schroeder
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-28       Impact factor: 15.336

3.  Selective MS screening reveals a sex pheromone in Caenorhabditis briggsae and species-specificity in indole ascaroside signalling.

Authors:  Chuanfu Dong; Franziska Dolke; Stephan H von Reuss
Journal:  Org Biomol Chem       Date:  2016-07-06       Impact factor: 3.876

4.  Succinylated octopamine ascarosides and a new pathway of biogenic amine metabolism in Caenorhabditis elegans.

Authors:  Alexander B Artyukhin; Joshua J Yim; Jagan Srinivasan; Yevgeniy Izrayelit; Neelanjan Bose; Stephan H von Reuss; Yeara Jo; James M Jordan; L Ryan Baugh; Micheong Cheong; Paul W Sternberg; Leon Avery; Frank C Schroeder
Journal:  J Biol Chem       Date:  2013-05-20       Impact factor: 5.157

5.  A shortcut to identifying small molecule signals that regulate behavior and development in Caenorhabditis elegans.

Authors:  Chirag Pungaliya; Jagan Srinivasan; Bennett W Fox; Rabia U Malik; Andreas H Ludewig; Paul W Sternberg; Frank C Schroeder
Journal:  Proc Natl Acad Sci U S A       Date:  2009-04-03       Impact factor: 11.205

6.  Small-molecule pheromones that control dauer development in Caenorhabditis elegans.

Authors:  Rebecca A Butcher; Masaki Fujita; Frank C Schroeder; Jon Clardy
Journal:  Nat Chem Biol       Date:  2007-06-10       Impact factor: 15.040

7.  Natural variation in a neuropeptide Y receptor homolog modifies social behavior and food response in C. elegans.

Authors:  M de Bono; C I Bargmann
Journal:  Cell       Date:  1998-09-04       Impact factor: 41.582

8.  Conserved nematode signalling molecules elicit plant defenses and pathogen resistance.

Authors:  Patricia Manosalva; Murli Manohar; Stephan H von Reuss; Shiyan Chen; Aline Koch; Fatma Kaplan; Andrea Choe; Robert J Micikas; Xiaohong Wang; Karl-Heinz Kogel; Paul W Sternberg; Valerie M Williamson; Frank C Schroeder; Daniel F Klessig
Journal:  Nat Commun       Date:  2015-07-23       Impact factor: 14.919

9.  Chromatin remodelling and antisense-mediated up-regulation of the developmental switch gene eud-1 control predatory feeding plasticity.

Authors:  Vahan Serobyan; Hua Xiao; Suryesh Namdeo; Christian Rödelsperger; Bogdan Sieriebriennikov; Hanh Witte; Waltraud Röseler; Ralf J Sommer
Journal:  Nat Commun       Date:  2016-08-04       Impact factor: 14.919

10.  Ascarosides coordinate the dispersal of a plant-parasitic nematode with the metamorphosis of its vector beetle.

Authors:  Lilin Zhao; Xinxing Zhang; Yanan Wei; Jiao Zhou; Wei Zhang; Peijun Qin; Satya Chinta; Xiangbo Kong; Yunpeng Liu; Haiying Yu; Songnian Hu; Zhen Zou; Rebecca A Butcher; Jianghua Sun
Journal:  Nat Commun       Date:  2016-08-01       Impact factor: 14.919
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  11 in total

1.  Prey sensing and response in a nematode-trapping fungus is governed by the MAPK pheromone response pathway.

Authors:  Sheng-An Chen; Hung-Che Lin; Frank C Schroeder; Yen-Ping Hsueh
Journal:  Genetics       Date:  2021-02-09       Impact factor: 4.562

Review 2.  Natural products as chemical tools to dissect complex biology in C. elegans.

Authors:  Rebecca A Butcher
Journal:  Curr Opin Chem Biol       Date:  2019-05-15       Impact factor: 8.822

3.  Natural diversity in the predatory behavior facilitates the establishment of a robust model strain for nematode-trapping fungi.

Authors:  Ching-Ting Yang; Guillermo Vidal-Diez de Ulzurrun; A Pedro Gonçalves; Hung-Che Lin; Ching-Wen Chang; Tsung-Yu Huang; Sheng-An Chen; Cheng-Kuo Lai; Isheng J Tsai; Frank C Schroeder; Jason E Stajich; Yen-Ping Hsueh
Journal:  Proc Natl Acad Sci U S A       Date:  2020-03-11       Impact factor: 11.205

4.  Social and sexual behaviors in C. elegans: the first fifty years.

Authors:  Douglas S Portman
Journal:  J Neurogenet       Date:  2020-11-04       Impact factor: 1.250

5.  A Large Family of Enzymes Responsible for the Modular Architecture of Nematode Pheromones.

Authors:  Nasser Faghih; Subhradeep Bhar; Yue Zhou; Abdul Rouf Dar; Kevin Mai; Laura S Bailey; Kari B Basso; Rebecca A Butcher
Journal:  J Am Chem Soc       Date:  2020-07-30       Impact factor: 15.419

6.  Comparative Ascaroside Profiling of Caenorhabditis Exometabolomes Reveals Species-Specific (ω) and (ω - 2)-Hydroxylation Downstream of Peroxisomal β-Oxidation.

Authors:  Chuanfu Dong; Douglas K Reilly; Célia Bergame; Franziska Dolke; Jagan Srinivasan; Stephan H von Reuss
Journal:  J Org Chem       Date:  2018-03-05       Impact factor: 4.354

7.  Photoaffinity probes for nematode pheromone receptor identification.

Authors:  Ying K Zhang; Douglas K Reilly; Jingfang Yu; Jagan Srinivasan; Frank C Schroeder
Journal:  Org Biomol Chem       Date:  2019-12-18       Impact factor: 3.876

8.  Nematode Signaling Molecules Are Extensively Metabolized by Animals, Plants, and Microorganisms.

Authors:  Yan Yu; Ying K Zhang; Murli Manohar; Alexander B Artyukhin; Anshu Kumari; Francisco J Tenjo-Castano; Hung Nguyen; Pratyush Routray; Andrea Choe; Daniel F Klessig; Frank C Schroeder
Journal:  ACS Chem Biol       Date:  2021-05-21       Impact factor: 4.634

9.  Influence of Configuration at the 4- and 6-Positions on the Conformation and Anomeric Reactivity and Selectivity of 7-Deoxyheptopyranosyl Donors: Discovery of a Highly Equatorially Selective l-glycero-d-gluco-Heptopyranosyl Donor.

Authors:  Kapil Upadhyaya; Rahul S Bagul; David Crich
Journal:  J Org Chem       Date:  2021-08-03       Impact factor: 4.198

10.  Selection and gene flow shape niche-associated variation in pheromone response.

Authors:  Daehan Lee; Stefan Zdraljevic; Daniel E Cook; Lise Frézal; Jung-Chen Hsu; Mark G Sterken; Joost A G Riksen; John Wang; Jan E Kammenga; Christian Braendle; Marie-Anne Félix; Frank C Schroeder; Erik C Andersen
Journal:  Nat Ecol Evol       Date:  2019-09-23       Impact factor: 15.460
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