Home
Resources
Publications
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

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

Martin Peters, Melanie Trobe, Rolf Breinbauer

Chemistry. 2013 Feb 11;19(7):2450-6.

PMID: 23281154

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP1217891718	9-Methyl-9H-carbazole-3-boronic acid pinacol ester	1217891-71-8	Price
AP288101484	2,4-Difluorophenylboronic acid pinacol ester	288101-48-4	Price
AP365564074	3,5-Dimethoxyphenylboronic acid pinacol ester	365564-07-4	Price
LS793389	(4-methoxycarbonylmethylphenyl)boronic acid pinacol ester		Price
LS793402	benzenesulfonamide-3-boronic acid pinacol ester		Price
LS793444	4-Cyanomethoxy-3,5-dimethylphenylboronic acid pinacol ester		Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: