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

Funder ED, Jensen AB, Tørring T, Kodal AL, Azcargorta AR, Gothelf KV.

J Org Chem. 2012 Apr 6;77(7):3134-42. doi: 10.1021/jo2025477. Epub 2012 Mar 14.

Danish National Research Foundation, Center for DNA Nanotechnology (CDNA), Department of Chemistry and iNANO, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark.

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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