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High affinity agonists of the neuropeptide Y (NPY) Y4 receptor derived from the C-terminal pentapeptide of human pancreatic polypeptide (hPP): synthesis, stereochemical discrimination and radiolabeling

Kuhn, Kilian K., Ertl, Thomas, Dukorn, Stefanie, Keller, Max, Bernhardt, Günther, Reiser, Oliver and Buschauer, Armin (2016) High affinity agonists of the neuropeptide Y (NPY) Y4 receptor derived from the C-terminal pentapeptide of human pancreatic polypeptide (hPP): synthesis, stereochemical discrimination and radiolabeling. Journal of Medicinal Chemistry 59 (13), pp. 6045-6058.

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Abstract

The diastereomeric mixture of D/L-2,7-diaminooctanedioyl-bis(YRLRY-NH2) (BVD-74D, 2) was described in the literature as a high affinity Y4 receptor agonist. Here we report on the synthesis and pharmacological characterization of the pure diastereomers (2R,7R)- and (2S,7S)-2 and a series of homo- and heterodimeric analogues in which octanedioic acid was used as an achiral linker. To investigate ...

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Item type:Article
Date:25 May 2016
Additional Information (public):Supplementary material available
Institutions:Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Projects:GRK 1910, Graduiertenkolleg "Medicinal Chemistry of Selective GPCR Ligands"
Identification Number:
ValueType
10.1021/acs.jmedchem.6b00309DOI
27223253PubMed ID
Related URLs:
URLURL Type
http://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.6b00309Publisher
Keywords:Bioisosteric replacement, carbamoylguanidine, cross-metathesis, diastereomers, neuropeptide Y, NPY Y4 receptor agonist, pancreatic polypeptide, radioligand
Dewey Decimal Classification:500 Science > 540 Chemistry & allied sciences
600 Technology > 615 Pharmacy
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Item ID:33565
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