Issue 10, 2011

Radical arylation of tyrosine and its application in the synthesis of a highly selective neurotensin receptor 2 ligand

Abstract

A small library of Fmoc-protected 3-arylated tyrosines was created by radical arylation. The new building blocks were successfully applied in the synthesis of two novel neurotensin receptor ligands. Both isomers showed high affinity for the human NTS2 receptor with Ki values in the nanomolar range. Interestingly, subtype selectivity strongly depends on the configuration of the peptide in position 11. Isomer (11R)-3 displayed an excellent preference for NTS2 compared to NTS1.

Graphical abstract: Radical arylation of tyrosine and its application in the synthesis of a highly selective neurotensin receptor 2 ligand

Supplementary files

Article information

Article type
Paper
Submitted
23 Feb 2011
Accepted
14 Mar 2011
First published
14 Mar 2011

Org. Biomol. Chem., 2011,9, 3746-3752

Radical arylation of tyrosine and its application in the synthesis of a highly selective neurotensin receptor 2 ligand

G. Pratsch, J. F. Unfried, J. Einsiedel, M. Plomer, H. Hübner, P. Gmeiner and M. R. Heinrich, Org. Biomol. Chem., 2011, 9, 3746 DOI: 10.1039/C1OB05292F

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