Mal-PEG2-COOH

Base Information

• Chemical Name: Mal-PEG2-COOH
• CAS No.: 756525-98-1
• Molecular Formula: C14H20N2O7
• Molecular Weight: 328.322
• Mol file: 756525-98-1.mol

Synonyms:Propanoic acid, 3-[2-[2-[[3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxopropyl]amino]ethoxy]ethoxy]-;

Chemical Property of Mal-PEG2-COOH

Chemical Property:

• Boiling Point: 617.3±55.0 °C(Predicted)
• PKA: 4.28±0.10(Predicted)
• PSA: 122.24000
• Density: 1.318±0.06 g/cm3(Predicted)
• LogP: -0.74560

Purity/Quality:

98%,99%, ^*data from raw suppliers

Maleimide-NH-PEG2-CH2CH2COOH min.97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Mal-amido-PEG2-acid is a PEG linker containing a maleimide group and a terminal carboxylic acid. The hydrophilic PEG spacer increases solubility in aqueous media. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Technology Process of Mal-PEG2-COOH

There total 10 articles about Mal-PEG2-COOH 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: 88.0%

tert-butyl 3-(2-{2-[3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido]ethoxy}ethoxy)propanoate → 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)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 10 - 20 ℃; for 1h;

DOI:10.1055/s-0033-1340980

Reference yield: 79.0%

3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoyl chloride (121215-45-0) + amino-PEG(2u)-acid (791028-27-8) → 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)

Guidance literature:

amino-PEG(2u)-acid; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 - 25 ℃; Large scale;

3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoyl chloride; In dichloromethane; at 20 ℃; Large scale;

Reference yield: 48.0%

3-maleimidopropionic acid N-hydroxysuccinimide ester (55750-62-4) + amino-PEG(2u)-acid (791028-27-8) → 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)

Guidance literature:

With sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 20 ℃; for 2h;

upstream raw materials:

2-methyl-2-propanyl 3-[2-(2-aminoethoxy)ethoxy]propanoate

3-maleimidepropionic acid

3-maleimidopropionic acid N-hydroxysuccinimide ester

2-methyl-2-propanyl 3-[2-(2-hydroxyethoxy)ethoxy]propanoate

Downstream raw materials:

3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-{2-[2-(3-oxo-3-{4-[3-oxo-3-(2-oxoazetidin-1-yl)propyl]phenylamino}propoxy)ethoxy]ethyl}propanamide

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

Refernces

• 1、 -. "Antibody drug conjugate, intermediate, preparation method, pharmaceutical composition and uses thereof". . . Retrieved 2019/11/11.
• 2、 Palanki, Moorthy S.S.,Bhat, Abhijit,Lappe, Rodney W.,Liu, Bin,Oates, Bryan,Rizzo, John,Stankovic, Nebojsa,Bradshaw, Curt. "Development of novel linkers to conjugate pharmacophores to a carrier antibody". . p. 4249 - 4253. Retrieved 2012/07/17.