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Synthesis of dopamine and serotonin derivatives for immobilization on a solid support.

Authors
  • Funder, Erik Daa1
  • Jensen, Anne Bjørnskov
  • Tørring, Thomas
  • Kodal, Anne Louise Bank
  • Azcargorta, Ane Rebolledo
  • Gothelf, Kurt Vesterager
  • 1 Danish National Research Foundation, Center for DNA Nanotechnology (CDNA), Department of Chemistry and iNANO, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark. , (Denmark)
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Apr 06, 2012
Volume
77
Issue
7
Pages
3134–3142
Identifiers
DOI: 10.1021/jo2025477
PMID: 22390263
Source
Medline
License
Unknown

Abstract

The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.

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