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Carboxymethyl glycoside lactone (CMGL) synthons: Scope of the method and preliminary results on step growth polymerization of α-azide-ω-alkyne glycomonomers

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Abstract

Carboxymethyl glycoside lactones (CMGLs) are bicyclic synthons which open readily for accessing new types of pseudo-glycoconjugates, such as sugar-amino acid hybrids, neoglycolipids, pseudodisaccharides, and membrane imaging systems. After lactone opening, free OH-2 is available for further functionalization, leading to 1,2-bisfunctionalized derivatives. This strategy is illustrated herein with new polymerizable systems of the AB type bearing both azide and alkyne functions prepared from α or β gluco-CMGL synthons. After the reaction of lactones with propargylamine, an azido group was introduced by two different sequences leading to either the 2-manno-azido or the 6-gluco-azido products. The capability of these AB monomers to undergo step growth polymerization through copper(I) catalyzed alkyne-azide cycloaddition (CuAAC) and generate glycopolytriazoles was evidenced.

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Author notes

  1. Jie Chen

    Present address: Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China

Authors and Affiliations

  1. INSA-Lyon, Laboratoire de Chimie Organique et Bioorganique, Bât. J. Verne, 20 Avenue A. Einstein, 69621, Villeurbanne Cedex, France

    Jie Chen, Yong Miao, Stéphane Chambert & Yves Queneau

  2. ICBMS, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, UMR5246; CNRS, université de Lyon; université Lyon 1; INSA-Lyon; CPE-Lyon, Bât. Curien, 43 Bd du 11 Novembre 1918, F 69622, Villeurbanne, France

    Jie Chen, Yong Miao, Stéphane Chambert & Yves Queneau

  3. IMP, 1ngénierie des Matériaux Polymères, INSA-LYON, Bât. J. Verne, 20 Avenue A. Einstein, 69621, Villeurbanne Cedex, France

    Julien Bernard & Etienne Fleury

  4. UMR5223; CNRS, université de Lyon, université Claude Bernard Lyon 1, F-69621, Villeurbanne Cedex, France

    Julien Bernard & Etienne Fleury

Authors
  1. Jie Chen
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  2. Yong Miao
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  6. Yves Queneau
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Correspondence to Yves Queneau.

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Chen, J., Miao, Y., Chambert, S. et al. Carboxymethyl glycoside lactone (CMGL) synthons: Scope of the method and preliminary results on step growth polymerization of α-azide-ω-alkyne glycomonomers. Sci. China Chem. 53, 1880–1887 (2010). https://doi.org/10.1007/s11426-010-4058-0

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