N-Succinimidyl maleimidoacetate Chemical Properties

Melting point:

174-175°C

Boiling point:

430.1±47.0 °C(Predicted)

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated)

pka

-2.69±0.20(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C10H8N2O6/c13-6-1-2-7(14)11(6)5-10(17)18-12-8(15)3-4-9(12)16/h1-2H,3-5H2

InChIKey

TYKASZBHFXBROF-UHFFFAOYSA-N

SMILES

N1(CC(ON2C(=O)CCC2=O)=O)C(=O)C=CC1=O

CAS DataBase Reference

55750-61-3

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

N-Succinimidyl maleimidoacetate Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

Maleimidoacetic acid N-hydroxysuccinimide ester is a crosslinking reagent that contains NHS ester- and maleimide-reactive groups at the opposite ends of a 4.4 ? spacer arm. This configuration allows for sequential, two-stage conjugation with amine and sulfhydryl functional groups in the preparation of protein-hapten or protein-protein conjugates.

Uses

A hetero-bifunctional cross-linking reagent for the preparation of protein-protein or protein-hapten conjugates.

reaction suitability

reagent type: linker

Synthesis

GENERAL STEPS: To a 500 mL three-necked flask was added N-maleimidoacetic acid (94 g, 0.6 mol) and 300 mL of methylene chloride, followed by oxalyl chloride (90 g, 0.72 mol). The reaction mixture was heated to reflux and a large amount of gas was observed to be released. After 2 hours of reaction, the solution became clarified. Subsequently, dichloromethane and excess oxalyl chloride were removed by concentration. 200 mL of dichloromethane was added to wash and remove the residual acid to give the crude product N-maleimidoacetyl chloride. The crude product was dissolved in 200 mL of dichloromethane. In another vessel, N-hydroxysuccinimide (69 g, 0.6 mol) and triethylamine (80.8 g, 0.8 mol) were dissolved in 300 mL of dichloromethane and the reaction temperature was controlled to be no more than 20° C. under the cooling of an ice water bath. A dichloromethane solution of the above N-maleimidoacetyl chloride was slowly added dropwise to this mixture and the dropwise process lasted for 2 hours. Upon completion of the reaction, the reaction solution was washed with 200 mL of water to remove the triethylamine hydrochloride, followed by 100 mL of 1N hydrochloric acid to remove excess triethylamine, and finally with 200 mL of saturated brine. The organic phase was dried and concentrated to dryness to give 137 g of white solid. Purification by recrystallization in a mixed solvent of ethyl acetate and petroleum ether resulted in 116 g of white solid with 98.7% HPLC purity and 76.7% yield.

IC 50

Non-cleavable Linker

References

[1] Patent: CN105037237, 2017, B. Location in patent: Paragraph 0071-0074

N-Succinimidyl maleimidoacetate(55750-61-3)Related Product Information

• Chloromethyl ethyl carbonate
• Diisopropyl chlorophosphate
• ETHYL CHLOROSULFONATE
• Suberate Bis(sulfosuccinimidyl) Sodium Salt
• BUTYL OLEATE
• Ethyl 2-(Chlorosulfonyl)acetate
• Maleimide
• Methyl acrylate
• O-Phthalimide
• N-Chlorosuccinimide
• N-Hydroxysuccinimide
• Tris(trimethylsilyl)phosphate
• Succinimide
• Bismaleimide
• DIALIFOS
• 1-(2-HYDROXY-ETHYL)-PYRROLE-2,5-DIONE
• 2-Maleimido acetic acid
• AC-GLY-OSU