α,ω-dipropionic acid tetraethylene glycol

Description

Bis-PEG5-acid is a PEG linker containing two terminal carboxylic acid groups. The hydrophilic PEG spacer increases solubility in aqueous media. The terminal carboxylic acids can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Uses

A dicarboxylic acid used in the preparation of potent dimeric inhibitors of the PSD-95-NMDA receptor interaction.

Uses

As a dicarboxylic acid, 4,7,10,13,16-Pentaoxanonadecanedioic Acid can be used in the preparation of potent dimeric inhibitors of the PSD-95-NMDA receptor interaction.

Synthesis

The general procedure for the synthesis of 4,7,10,13,16-pentaoxa-nineteenthane-1,19-dioic acid from di-tert-butyl 4,7,10,13,16-pentaoxa-nineteenthane-1,19-dioic acid is as follows: tert-butyl 3-{2-[2-[2-(2-{2-[2-(2-tert-butyloxycarbonyl-ethoxy)ethoxy]ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionate (6 g, 18.6 mmol) was dissolved in anisole (20 ml) and cooled in an ice bath. Subsequently, trifluoroacetic acid (65 g) was added slowly. The reaction mixture was stirred at room temperature for 3 hours and the volatiles were removed by distillation under reduced pressure. The residue was extracted by partitioning between ethyl acetate (50 ml) and 5% sodium bicarbonate solution. The aqueous layer was acidified with 1N HCl to pH<2, then saturated with NaCl and extracted with ethyl acetate (3 x 50 ml). The organic layers were combined, washed with saturated brine and dried with anhydrous sodium sulfate. Finally, the solvent was removed by distillation under reduced pressure to afford the target product 4,7,10,13,16-pentaoxadecane-1,19-dioic acid as a colorless liquid, which solidified to a white solid after refrigeration (3.8 g, 82% yield).

IC 50

PEGs

References

[1] Patent: US2006/205670, 2006, A1. Location in patent: Page/Page column 103
[2] Patent: US2008/166364, 2008, A1. Location in patent: Page/Page column 104-105