Issue 10, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Gerald Pratsch,a   Johannes F. Unfried,a   Jürgen Einsiedel,a   Manuel Plomer,a   Harald Hübner,a   Peter Gmeinera  and  Markus R. Heinrich*a  

* Corresponding authors

a Department für Chemie und Pharmazie, Pharmazeutische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen, Germany
E-mail: Markus.Heinrich@medchem.uni-erlangen.de
Fax: +49-9131-85-22585
Tel: +49-9131-85-24115

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1OB05292F
Article type
Paper
Submitted
23 Feb 2011
Accepted
14 Mar 2011
First published
14 Mar 2011

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements