N-Succinimidyl 3-maleimidopropionate Chemical Properties

Melting point:

168-170 °C(lit.)

Boiling point:

448.8±47.0 °C(Predicted)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-2.39±0.20(Predicted)

color 

White to Light Brown

Appearance

white crystals

Water Solubility 

Insoluble in water.

Sensitive 

Moisture Sensitive

BRN 

1492578

InChI

InChI=1S/C11H10N2O6/c14-7-1-2-8(15)12(7)6-5-11(18)19-13-9(16)3-4-10(13)17/h1-2H,3-6H2

InChIKey

JKHVDAUOODACDU-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

55750-62-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37

Safety Statements 

26-36/37/39-24/25

WGK Germany 

3

F 

10-21

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

N-Succinimidyl 3-maleimidopropionate Usage And Synthesis

Description

3-Maleimido-propionic NHS ester contains a maleimide group and an NHS ester. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Chemical Properties

White to off-white solid

Uses

3-Maleimidopropionic acid N-hydroxysuccinimide ester is a reagent that is widely used for generating stable maleimide-activated carrier proteins that can spontaneously react with sulfhydryls. Alternatively these relatively stable maleimide-activated intermediates may be lyophilized and stored for later conjugation to a hapten.

Uses

A short, sulfhydryl and amino reactive heterobifunctional crosslinking reagent, N-Succinimidyl 3-maleimidopropionate can also been used in immunodiagnostics.

reaction suitability

reagent type: linker

Synthesis

Example 1: Synthesis of NHS esters of N-maleimidopropionic acid 1. Maleic anhydride, β-alanine (1 mole equivalent) and acetonitrile (ACN, 25 v/v) were added to a reaction vessel under nitrogen protection to form a slurry. 2. The slurry was heated to 70 °C and kept stirring for 5-8 hours. 3. After completion of the reaction, cooled to 5 °C, N-hydroxybutanediimide (NHS, 1 mole equivalent) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDCI, 1 mole equivalent) were added sequentially. 4. After maintaining the temperature at 0-5 °C for 1 hour of reaction, EDCI (1 molar equivalent) was added again. 5. The reaction mixture was heated to 70 °C and kept stirring for 7 hours. 6. At the end of the reaction, the mixture was cooled to 20 °C and concentrated under vacuum at a temperature not exceeding 45 °C until the rate of solvent distillation was significantly reduced. 7. Dichloromethane (DCM, 40 v/v) was added to the residue and stirred until completely dissolved. 8. The organic phase was washed sequentially with 12% w/w aqueous ammonium chloride (25 wt. eq.) and 24% w/w aqueous sodium chloride (25 wt. eq.). 9. Add magnesium sulfate (1 w/w) to dry the organic solution and stir for 1-2 hours at ambient temperature. 10. Vacuum filtered to remove inorganic salts and the filter cake was washed with DCM (4 v/v). 11. Vacuum concentrate the filtrate while gradually replacing the DCM with isopropyl acetate (IPAC). 12. The resulting slurry was cooled to ambient temperature, stirred for 1 hour and vacuum filtered. 13. The product filter cake was washed with IPAC (4 v/v) and subsequently rotary dried under vacuum at 40 °C to constant weight to give an off-white solid product. 14. Typical yields were 60-80% of the theoretical maximum yield. Product characterization: 1H NMR (400 MHz, d6-DMSO): δ 2.80 (4H, br s), δ 3.05 (2H, t, J~7 Hz), δ 3.75 (2H, t, J~7 Hz), δ 7.05 (2H, s).

IC 50

Non-cleavable Linker

References

[1] Patent: WO2011/23680, 2011, A2. Location in patent: Page/Page column 13-14
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10198 - 10201
[3] Angew. Chem., 2015, vol. 127, p. 10336 - 10339
[4] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10582 - 10585
[5] Journal of the American Chemical Society, 2004, vol. 126, # 3, p. 734 - 735

N-Succinimidyl 3-maleimidopropionate(55750-62-4)Related Product Information

• N-Succinimidyl 6-maleimidohexanoate
• N-Chlorosuccinimide
• Bismaleimide
• Methyl acrylate
• Succinimide
• BUTYL OLEATE
• N-Hydroxysuccinimide
• Tris(trimethylsilyl)phosphate
• O-Phthalimide
• 3-(4-Hydroxyphenyl)propionic acid
• DIALIFOS
• N-Ethylmaleimide
• 3-Maleimidopropionic acid
• N-PROPYLMALEIMIDE
• Maleimide
• 2-OXOCYCLOHEXANECARBONITRILE
• 3-Acryloylamino-1-propanol solution, 50% in water
• MALEIMIDOPROPIONIC ACID N-HYDROXYSULPHOSUCCINIMIDE ESTER