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- Title
A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 2: Synthesis of 5-Pyridine Boronic Acid Pinacol Ester Building Blocks with Amino Acid Side Chains in 3-Position.
- Authors
Peters, Martin; Trobe, Melanie; Breinbauer, Rolf
- Abstract
One of the most common protein-protein interactions (PPI) is the interaction of the α-helix of one protein with the surface of the second one. Terphenylic scaffolds are bioinspired motifs in the inhibition of PPIs and have been identified as suitable α-helix mimetics. One of the challenging aspects of this strategy is the poor solubility of terphenyls under physiological conditions. In the literature pyrrolopyrimidine-, pyrimidine- or pyridazine-based mimetics have been reported to show improved solubility. We present a new convergent strategy for the synthesis of linear pyridine-type teraryls based on a phenylic core unit. A general approach for the synthesis of 3,5-disubstituted pyridine-based boronic acid pinacol esters with amino acid side chains in the 3-position (representing Phe, Leu, Ile, Lys, Asp, Asn) is presented and exploits the functional group tolerance of the Knochel-Grignard reagents. The building blocks have been used in a convergent in situ two-step synthesis of teraryl α-helix mimetics.
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 7, p2450
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201203006