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Issue 10, 2018
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An organocatalyzed Stetter reaction as a bio-inspired tool for the synthesis of nucleic acid-based bioconjugates

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Abstract

An N-Heterocyclic Carbene (NHC) catalyzed biomimetic Stetter reaction was applied for the first time as a bioconjugation reaction to sensitive nucleoside-type biomolecules to provide original pyrrole linked nucleolipids. A versatile approach allowed the functionalization of thymidine at the three reactive positions (O-5′, O-3′ and N-3) providing a structural diversity oriented synthesis. This strategy was applied to the synthesis of an original glyconucleolipid amphiphile in the hope that the pyrrole aromatic moiety would induce additional self-assembling properties.

Graphical abstract: An organocatalyzed Stetter reaction as a bio-inspired tool for the synthesis of nucleic acid-based bioconjugates

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Publication details

The article was received on 23 Jan 2018, accepted on 12 Feb 2018 and first published on 15 Feb 2018


Article type: Paper
DOI: 10.1039/C8OB00192H
Citation: Org. Biomol. Chem., 2018,16, 1760-1769
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    An organocatalyzed Stetter reaction as a bio-inspired tool for the synthesis of nucleic acid-based bioconjugates

    A. Hamoud, P. Barthélémy and V. Desvergnes, Org. Biomol. Chem., 2018, 16, 1760
    DOI: 10.1039/C8OB00192H

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