N-Succinimidyl 3-maleimidopropionate
- Product Name
- N-Succinimidyl 3-maleimidopropionate
- CAS No.
- 55750-62-4
- Chemical Name
- N-Succinimidyl 3-maleimidopropionate
- Synonyms
- 2,5-Dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate;3-MALEIMIDOPROPIONIC ACID N-SUCCINIMIDYL ESTER;(2,5-Dioxopyrrolidin-1-yl) 3-(2,5-dioxopyrrol-1-yl)propanoate;BMPS Crosslinker;Mal-beta-Ala-OSu;Cross-linkingReagent;MaleiMide-(CH2)2-NHS;NHS-(CH2)2-Mal (BMPS);3-Maleimidopropionic acid NHS;3-Maleimido-propionic NHS este
- CBNumber
- CB7132511
- Molecular Formula
- C11H10N2O6
- Formula Weight
- 266.21
- MOL File
- 55750-62-4.mol
N-Succinimidyl 3-maleimidopropionate Property
- 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
- Hazard Codes
- Xi
- Risk Statements
- 37
- Safety Statements
- 26-36/37/39-24/25
- WGK Germany
- 3
- F
- 10-21
- HS Code
- 29280000
N-Bromosuccinimide Price
- Product number
- 63179
- Product name
- 3-(Maleimido)propionic acid N-hydroxysuccinimide ester
- Purity
- ≥98.5% (HPLC)
- Packaging
- 25mg
- Price
- $225
- Updated
- 2025/07/31
- Product number
- 63179
- Product name
- 3-(Maleimido)propionic acid N-hydroxysuccinimide ester
- Purity
- ≥98.5% (HPLC)
- Packaging
- 100mg
- Price
- $682
- Updated
- 2025/07/31
- Product number
- 358657
- Product name
- 3-Maleimidopropionic acid N-hydroxysuccinimide ester
- Purity
- 99%
- Packaging
- 25mg
- Price
- $217
- Updated
- 2025/07/31
- Product number
- S0427
- Product name
- N-Succinimidyl 3-Maleimidopropionate [Cross-linking Reagent]
- Purity
- >98.0%(HPLC)(N)
- Packaging
- 100mg
- Price
- $73
- Updated
- 2025/07/31
- Product number
- S0427
- Product name
- N-Succinimidyl 3-Maleimidopropionate [Cross-linking Reagent]
- Purity
- >98.0%(HPLC)(N)
- Packaging
- 1g
- Price
- $219
- Updated
- 2025/07/31
N-Succinimidyl 3-maleimidopropionate Chemical Properties,Usage,Production
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
108-31-6
6066-82-6
107-95-9
55750-62-4
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from N-Succinimidyl 3-maleimidopropionate manufacturers
- Product
- N-Succinimidyl 3-maleimidopropionate 55750-62-4
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10000KGS
- Release date
- 2025-09-18
- Product
- N-Succinimidyl 3-maleimidopropionate 55750-62-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-09-26
- Product
- N-Succinimidyl 3-maleimidopropionate 55750-62-4
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10