O-(2-AMinoethyl)-O'-[2-(Boc-aMino)ethyl]tetraethylene Glycol Chemical Properties

storage temp. 

2-8°C(protect from light)

solubility 

Soluble in Water, DMSO, DCM, DMF

form 

Liquid

color 

Colorless to light yellow

Safety Information

HS Code 

2918999090

O-(2-AMinoethyl)-O'-[2-(Boc-aMino)ethyl]tetraethylene Glycol Usage And Synthesis

Description

t-Boc-N-Amido-PEG5-amine is a Boc protected PEG linker containing an free amino group and5 PEG units. The hydrophilic PEG spacer increases solubility in aqueous media. The amino group is reactive with carboxylic acids, activated NHS esters. The Boc group can be deprotected under mild acidic conditions to free the amine.

Uses

As a polyethyleneglycol (PEG) derivative, O-(2-AMinoethyl)-O'-[2-(Boc-aMino)ethyl]tetraethylene Glycol can be used in the preparation of novel biochip technology for detection of explosives-TNT. It is also used as a reagent in the synthesis of chemical inducer of dimeriza tions (CID) to identify the protein target of inhibitors of Toxoplasma gondii invasion.

Synthesis

General procedure for the synthesis of tert-butyl (17-amino-3,6,9,12,15-pentaoxaheptadecyl)carbamate from (17-azido-3,6,9,12,15-pentaoxaheptadecyl)carbamate: Compound 6 (5-PEG-Boc-Amino azide, 2.90 g, 8.0 mmol) was dissolved in a Parr reaction flask in 100 ml of ethyl acetate and 0.25 g of 10% Pd/C catalyst was added. The reaction mixture was stirred overnight under hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was diluted with 200 ml of ethyl acetate and filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure to remove the solvent to give 2.41 g of crude product. The crude product was purified by silica gel column chromatography, first eluting using a mixed solvent system of 1% NH4OH/15% MeOH/84% CH2Cl2, and then switching to a mixed solvent system of 1% NH4OH/25% MeOH/74% CH2Cl2, and the target fractions were collected to give 1.37 g of purified product. The purified product was dissolved in toluene and concentrated again under reduced pressure to give 1.21 g (40% yield) of the target compound 7.

IC 50

PEGs; Alkyl/ether

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 586 - 590
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 15, p. 3049 - 3060
[3] Synlett, 2015, vol. 26, # 19, p. 2707 - 2713
[4] Patent: US7230101, 2007, B1. Location in patent: Page/Page column 60; 79

O-(2-AMinoethyl)-O'-[2-(Boc-aMino)ethyl]tetraethylene Glycol(189209-27-6)Related Product Information

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