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Brinkø A, Risinger C, Lambert A, et al. Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics. Org Lett. 2019;21(18):7544-7548doi: 10.1021/acs.orglett.9b02811.
Brinkø, A., Risinger, C., Lambert, A., Blixt, O., Grandjean, C., & Jensen, H. H. (2019). Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics. Organic letters, 21(18), 7544-7548. https://doi.org/10.1021/acs.orglett.9b02811
Brinkø, Anne, et al. "Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics." Organic letters vol. 21,18 (2019): 7544-7548. doi: https://doi.org/10.1021/acs.orglett.9b02811
Brinkø A, Risinger C, Lambert A, Blixt O, Grandjean C, Jensen HH. Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics. Org Lett. 2019 Sep 20;21(18):7544-7548. doi: 10.1021/acs.orglett.9b02811. Epub 2019 Sep 10. PMID: 31502847.
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Org Lett. 2019 Sep 20;21(18):7544-7548. doi: 10.1021/acs.orglett.9b02811. Epub 2019 Sep 10.

Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics.

Organic letters

Anne Brinkø, Christian Risinger, Annie Lambert, Ola Blixt, Cyrille Grandjean, Henrik H Jensen

Affiliations

  1. Department of Chemistry , Aarhus University , Langelandsgade 140 , 8000 Aarhus C, Denmark.
  2. Department of Chemistry, Chemical Biology , University of Copenhagen , Thorvaldsensvej 40 , 1871 Frederiksberg C, Denmark.
  3. Faculté des Sciences et des Techniques, Unité Fonctionnalité et Ingénierie des Protéines (UFIP) , Université de Nantes , UMR CNRS 6286, 2, rue de la Houssinière , BP92208, 44322 Nantes Cedex 3, France.

PMID: 31502847 DOI: 10.1021/acs.orglett.9b02811

Abstract

Here, we report on the first combined one-pot use of the two so-called "click reactions": the thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

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