α-Maleimidopropionyl-ω-succinimidyl-2(ethylene glycol)

Base Information

• Chemical Name: α-Maleimidopropionyl-ω-succinimidyl-2(ethylene glycol)
• CAS No.: 955094-26-5
• Molecular Formula: C18H23N3O9
• Molecular Weight: 425.395
• Hs Code.: 29280000
• Mol file: 955094-26-5.mol

Synonyms:α-Maleimidopropionyl-ω-succinimidyl-2(ethylene glycol);alpha-MaleiMidopropionyl-oMega-succiniMidyl-2(ethylene glycol);Mal-PEG2-NHS;MaleiMide-NH-PEG2-NHS Ester;MaleiMide-NH-PEG2-CH2CH2COONHS Ester;3-[2-[2-[[3-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxopropyl]amino]ethoxy]ethoxy]propanoic acid 2,5-dioxo-1-pyrrolidinyl ester;MaleiMide-PEG2-succiniMidyl ester;MaleiMide-PEG2-suciniMidyl ester

Chemical Property of α-Maleimidopropionyl-ω-succinimidyl-2(ethylene glycol)

Chemical Property:

• Melting Point: 90.0 to 94.0 °C
• PKA: 15.00±0.46(Predicted)
• PSA: 148.62000
• Density: 1.41±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: -1.28510
• Storage Temp.: ?20°C

Purity/Quality:

97% ^*data from raw suppliers

2,5-Dioxopyrrolidin-1-yl3-(2-(2-(3-(2,5-Dioxo-2H-pyrrol-1(5H)-yl)propanamido)ethoxy)ethoxy)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Mal-amido-PEG2-NHS is a PEG linker containing a maleimide group and an NHS ester. The hydrophilic PEG spacer increases solubility in aqueous media. 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.
• Uses: Heterobifunctional crosslinker with short ethylene oxide spacer for linking amine- to sulfhydryl-containing compounds or biomolecules. Maleimide functional group will react with sulfhydryls and the succinimidyl ester group will react with amines. Spacer length is 17.6 angstroms.

Technology Process of α-Maleimidopropionyl-ω-succinimidyl-2(ethylene glycol)

There total 5 articles about α-Maleimidopropionyl-ω-succinimidyl-2(ethylene glycol) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + C14H19ClN2O6 → 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-[2-(2-{3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropoxy}ethoxy)ethyl]propanamide (955094-26-5,326003-46-7,1426151-00-9)

Guidance literature:

1-hydroxy-pyrrolidine-2,5-dione; With triethylamine; In dichloromethane; at 20 - 25 ℃;

C₁₄H₁₉ClN₂O₆; In dichloromethane; at 20 ℃;

Reference yield: 25.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-(2-{2-[3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido]ethoxy}ethoxy)propanoic acid (756525-98-1,871133-36-7) → 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-[2-(2-{3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropoxy}ethoxy)ethyl]propanamide (955094-26-5,326003-46-7,1426151-00-9)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

3-maleimidepropionic acid (7423-55-4) → 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-[2-(2-{3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropoxy}ethoxy)ethyl]propanamide (955094-26-5,326003-46-7,1426151-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C / Sealed tube

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 - 25 °C / Large scale

2.2: 20 °C / Large scale

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C

4.1: triethylamine / dichloromethane / 20 - 25 °C

4.2: 20 °C

With oxalyl dichloride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In dichloromethane;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

3-(2-{2-[3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido]ethoxy}ethoxy)propanoic acid

3-maleimidepropionic acid

3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoyl chloride