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| | N-Succinimidyl 6-maleimidohexanoate Basic information |
| | N-Succinimidyl 6-maleimidohexanoate Chemical Properties |
| Melting point | 70-73 °C(lit.) | | Boiling point | 480.6±47.0 °C(Predicted) | | density | 1.40±0.1 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | chloroform: 100mg/mL | | form | powder | | pka | -2.21±0.20(Predicted) | | color | Off-white to pale brown | | Sensitive | Light & Moisture Sensitive & Hygroscopic | | BRN | 1499815 | | InChI | InChI=1S/C14H16N2O6/c17-10-5-6-11(18)15(10)9-3-1-2-4-14(21)22-16-12(19)7-8-13(16)20/h5-6H,1-4,7-9H2 | | InChIKey | VLARLSIGSPVYHX-UHFFFAOYSA-N | | SMILES | N1(CCCCCC(ON2C(=O)CCC2=O)=O)C(=O)C=CC1=O | | CAS DataBase Reference | 55750-63-5(CAS DataBase Reference) |
| | N-Succinimidyl 6-maleimidohexanoate Usage And Synthesis |
| Description | Mal-heptanoic 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 cream colored crystals | | Uses | 6-Maleimidohexanoic acid N-hydroxysuccinimide ester can be used in:
- Synthesis of maleimide-activated carbohydrates for site-specific glycosylation of cysteine-containing peptides and proteins via maleimide-thiol ligation reaction.
- Synthesis of a glucuronide prodrug of doxorubicin bearing a maleimide side chain as an antitumor agent.
- Cross-linking oligonucleotides with the amino groups on the substrate to fabricate DNA microarrays.
| | reaction suitability | reagent type: linker | | Synthesis | Under nitrogen protection, 4.7 g (22 mmol) of 6-maleimidohexanoic acid (MC) and 25 g (22 mmol) of N-hydroxybutanediimide (HOSu) were dissolved in 50 ml of acetonitrile. Another 4.5 g (22 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) was dissolved in 25 ml of acetonitrile and the internal temperature was maintained. The DCC solution was slowly added dropwise to the reaction mixture at 0°C. The reaction mixture was stirred at 0 °C for 2 h. The reaction was then brought to room temperature and continued overnight. After completion of the reaction, the precipitate was removed by filtration and the filter cake was washed with acetonitrile (10 ml x 3). The filtrates were combined and concentrated to dryness under reduced pressure. The resulting oily product was dried under reduced pressure for 6 h at room temperature to give 6.4 g of a light brown solid, i.e., succinimidyl 6-(maleimido)hexanoate, in 95% yield. | | IC 50 | Non-cleavable Linker | | References | [1] Patent: CN107789630, 2018, A. Location in patent: Paragraph 0064; 0065; 0066
[2] Patent: WO2018/178060, 2018, A1. Location in patent: Page/Page column 58; 60; 61
[3] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[4] Patent: WO2015/95953, 2015, A1. Location in patent: Page/Page column 118
[5] Patent: WO2016/41082, 2016, A1. Location in patent: Page/Page column 97; 98 |
| | N-Succinimidyl 6-maleimidohexanoate Preparation Products And Raw materials |
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