H2N-PEG4-tBu Chemical Properties

Boiling point:

400.1±35.0 °C(Predicted)

Density 

1.040±0.06 g/cm3(Predicted)

refractive index 

n/D 1.4508

storage temp. 

-20°C

solubility 

Soluble in Water, DMSO, DCM, DMF

form 

clear liquid

pka

8.74±0.10(Predicted)

color 

Colorless to Light yellow

InChI

InChI=1S/C15H31NO6/c1-15(2,3)22-14(17)4-6-18-8-10-20-12-13-21-11-9-19-7-5-16/h4-13,16H2,1-3H3

InChIKey

PKESARRNSGIDRD-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CCOCCOCCOCCOCCN

CAS DataBase Reference

581065-95-4

Safety Information

HS Code 

2922190090

H2N-PEG4-tBu Usage And Synthesis

Description

Amino-PEG4-t-butyl ester is a PEG reagent containing an amino (NH2) and a t-butyl protected carboxyl group. The hydrophilic PEG spacer increases solubility in aqueous media. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The t-butyl protected carboxyl (Boc) can be deprotected under acidic conditions.

Uses

is a linker-cytotoxin conjugate. Linker-cytotoxin conjugate is related to antibody-cytotoxin and antibody-drug conjugates and related compounds.

reaction suitability

reagent type: cross-linking reagent

Synthesis

The general procedure for the synthesis of tert-butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate from 1-(p-toluenesulfonyloxy)-3,6,9,12-tetraoxapentadecan-15-oate is as follows: 150 g of the sulfonated crude product was dissolved in 200 mL of methylene chloride, followed by the addition of 100 g of ammonium hydroxide and 10 g of tetrabutyl ammonium bromide. The reaction mixture was warmed to 40 °C with continuous stirring for 24 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation. To the residue, 3 M hydrochloric acid solution was added and the pH was adjusted to 3. The organic phase was separated by extracting twice with 300 mL of dichloromethane. The pH of the aqueous phase was then adjusted to 9 with sodium hydroxide solution and extracted three times with 400 mL of dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and the solvent was removed by rotary evaporation to give 50 g of aminocapped product. The structure of the product was confirmed by NMR.

IC 50

PEGs; Alkyl/ether

References

[1] Patent: WO2012/166560, 2012, A1
[2] Patent: WO2013/192360, 2013, A1
[3] Patent: WO2013/185117, 2013, A1
[4] Patent: CN107235848, 2017, A. Location in patent: Paragraph 0021

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