| Identification | More | [Name]
N-Succinimidyl 3-maleimidopropionate | [CAS]
55750-62-4 | [Synonyms]
3-MALEIMIDOPROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER
3-MALEIMIDOPROPIONIC ACID N-SUCCINIMIDYL ESTER
MALEIMIDOPROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER
MPS
N-(3-MALEIMIDOPROPIONYLOXY)SUCCINIMIDE
N-MALEOYL-BETA-ALANINE N'-HYDROXYSUCCINIMIDE ESTER
N-SUCCINIMIDYL 3-MALEIMIDOPROPIONATE
3-Maleidopropionic acid N-hydroxysuccynimide ester (SMP)
B-MALEIMIDOPROPIONIC ACID N-*HYDROXYSUCCINIMIDE ESTE
Cross-linkingReagent
N-Succinimidyl3-maleinimidopropionate
N-SUCCINIMIDYL3-MALEIMIDOPROPIONATE[CROSS-LINKINGREAGENT]
3-Maleimidopropionic acid succinimidyl ester
3-Maleimidopropionic acid NHS
3-(Maleimido)propionic acid N-succinimidyl ester, BMPS, N-(3-Maleimidopropionyloxy)succinimide, N-Maleoyl-β-alanine Nμ-hydroxysuccinimide ester, N-Succinimidyl 3-maleimidopropionate
N-(3-Maleimidopropionyloxy)succinimide, N-Succinimidyl 3-maleimidopropionate, BMPS, N-Maleoyl-β-alanine Nμ-hydroxysuccinimide ester, N-Maleoyl-β-alanine N-hydroxysuccinimide ester
1-[3-[(2,5-Dioxopyrrolidin-1-yl)oxy]-3-oxopropyl]-1H-pyrrole-2,5-dione
2,5-Dioxo-2,5-dihydro-1H-pyrrole-1-propionic acid 2,5-dioxo-1-pyrrolidinyl ester
2,5-Dioxo-3-pyrroline-1-propionic acid 2,5-dioxopyrrolidine-1-yl ester
2,5-Dioxo-3-pyrroline-1-propionic acid succinimidyl ester | [EINECS(EC#)]
627-755-4 | [Molecular Formula]
C11H10N2O6 | [MDL Number]
MFCD00043141 | [Molecular Weight]
266.21 | [MOL File]
55750-62-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
168-170 °C(lit.) | [Boiling point ]
448.8±47.0 °C(Predicted) | [density ]
1.55±0.1 g/cm3(Predicted) | [storage temp. ]
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 | [Usage]
A short, sulfhydryl and amino reactive heterobifunctional crosslinking reagent. Also used in immunodiagnostics.
Spacer Arm: 6.9 Angstrom | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37:Irritating to the respiratory system. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29280000 |
| Hazard Information | Back Directory | [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 |
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