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)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-40

Safety Statements 

26-36/37-36

WGK Germany 

3

F 

8-10-21

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

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(55750-63-5)Related Product Information

• N-Succinimidyl 3-maleimidopropionate
• Maleimide
• O-Phthalimide
• Hexyl hexanoate
• Methyl acrylate
• Succinimide
• Bismaleimide
• BUTYL OLEATE
• Tris(trimethylsilyl)phosphate
• N-Chlorosuccinimide
• DIALIFOS
• 6-Maleimidocaproic acid
• SMCC crosslinker
• SULFO-SMCC
• N-Succinimidyl 6-maleimidohexanoate
• 6-MALEIMIDOCAPROIC ACID SULFO-N-SUCCINIMIDYL ESTER
• MAL-AMCHC-OSU
• SULPHO-SMCC