Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

Nathan Berthelot; Antoine Brossay; Virginie Gasciolli; Jean-Jacques Bono; Aurélie Baron; Jean-Marie Beau; Dominique Urban; François-Didier Boyer; Boris Vauzeilles

doi:10.1039/C7OB01201B

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Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs†

Nathan Berthelot,^a Antoine Brossay,^ab Virginie Gasciolli,^c Jean-Jacques Bono,^c Aurélie Baron,^a Jean-Marie Beau,

^ab Dominique Urban,^a François-Didier Boyer

*^ad and Boris Vauzeilles*^ab

Author affiliations

* Corresponding authors

^a Institut de Chimie des Substances Naturelles, CNRS UPR2301, Univ. Paris-Sud, Université Paris-Saclay, 1 av. de la Terrasse, F-91198 Gif-sur-Yvette, France
E-mail: francois-didier.boyer@cnrs.fr, boris.vauzeilles@cnrs.fr
Web: http://www.icsn.cnrs-gif.fr

^b Laboratoire de Synthèse de Biomolécules, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Univ. Paris-Sud, CNRS, Université Paris-Saclay, F-91405 Orsay, France
E-mail: boris.vauzeilles@u-psud.fr

^c LIPM, Université de Toulouse, INRA, CNRS, Castanet-Tolosan, France

^d Institut Jean-Pierre Bourgin, INRA, AgroParisTech, CNRS, Université Paris-Saclay, RD10, F-78026 Versailles, France
E-mail: francois.boyer@inra.fr

Abstract

Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide–alkyne cycloaddition. Their evaluation in a binding assay using LYR3, a putative lipo-chitooligosaccharide receptor in Medicago truncatula, shows a complete loss of binding.

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Article information

DOI: https://doi.org/10.1039/C7OB01201B
Article type: Paper
Submitted: 17 May 2017
Accepted: 30 Aug 2017
First published: 30 Aug 2017

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Org. Biomol. Chem., 2017,15, 7802-7812

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Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

N. Berthelot, A. Brossay, V. Gasciolli, J. Bono, A. Baron, J. Beau, D. Urban, F. Boyer and B. Vauzeilles, Org. Biomol. Chem., 2017, 15, 7802 DOI: 10.1039/C7OB01201B

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Organic & Biomolecular Chemistry

Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs†

Abstract

Supplementary files

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Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

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