| Identification | More | [Name]
N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate | [CAS]
64987-85-5 | [Synonyms]
4-(N-MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER
4-(N-MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER
N-SUCCINIMIDYL 4-(MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLATE
N-SUCCINIMIDYL 4-(MALEIMIDOMETHYL)CYCLOHEXANECARBOXYLATE
SMCC
SUCCINIMIDYL 4-[N-MALEIMIDO-METHYL]CYCLOHEXANE-1-CARBOXYLATE
SUCCINIMIDYL TRANS-4-(MALEIMIDYLMETHYL)CYCLOHEXANE-1-CARBOXYLATE
SUCCINIMIDYL-TRANS-4-(N-MALEIMIDOMETHYL)CYCLOHEXANE-1-CARBOXYLATE
SUCCINIMIDYL-TRANS-4-(N-MALEIMIDYLMETHYL)CYCLOHEXANE-1-CARBOXYLATE
TRANS-4-(N-MALEIMIDYLMETHYL)-CYCLO-HEXANE-1-CARBOXYLATE-N-HYDROXYSUCCINIMIDE ESTER
n-(4-carboxycyclohexylmethyl)maleimiden-hydroxysuccinimideester
N-succinimidyl 4-(maleimidome.)cyclo-hexanecarboxylate
4-(N-MALEIMIDOMETHYL)-CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER CRYSTALLINE
N-Succinimidyl-4-(N-maleimidomethyl)-cyclohexane-1-carboxylate
4-(maleimidomethyl)-1-cyclohexanecarboxylic acid N-hydroxy
N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C16H18N2O6 | [MDL Number]
MFCD00009634 | [Molecular Weight]
334.32 | [MOL File]
64987-85-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
180-182 °C (lit.) | [Boiling point ]
501.7±42.0 °C(Predicted) | [density ]
1.42±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
chloroform: 50 mg/mL
| [form ]
powder
| [pka]
-2.24±0.20(Predicted) | [color ]
White to Off-White | [Sensitive ]
Moisture & Light Sensitive | [Usage]
A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab?2 fragments to ?galactosidase. Conjugates hIgG to alkaline phosphatase.
Spacer Arm: 11.6 Angstrom | [BRN ]
1555271 | [InChI]
InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2 | [InChIKey]
JJAHTWIKCUJRDK-UHFFFAOYSA-N | [SMILES]
C1(C(ON2C(=O)CCC2=O)=O)CCC(CN2C(=O)C=CC2=O)CC1 | [CAS DataBase Reference]
64987-85-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29280000 |
| Hazard Information | Back Directory | [Description]
SMCC crosslinker(64987-85-5) is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. SMCC crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, and then can be added to an aqueous crosslinking reaction. SMCC crosslinking reagent is permeable across the lipid bilayer of the cell membrane and can be used to crosslink intracellular proteins and peptides. | [Chemical Properties]
White Crystalline Solid | [Uses]
A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab’)2 fragments to ?-galactosidase. Conjugates hIgG to alkaline phosphatase.
Spacer Arm: 11.6 Angstroms | [Definition]
ChEBI: An N-hydroxysuccinimide ester derived from 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid. | [General Description]
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (SMCC) is a heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. It is typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). SMCC contains nine atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers. | [Chemical Reactivity]
Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a non-cleavable and membrane permeable crosslinker. It contains an amine-reactive N -hydroxysuccinimide (NHS ester) and a sulfhydryl-reactive maleimide group. NHS esters react with primary amines at pH 7-9 to form stable amide bonds. Maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. The maleimide groups of SMCC and Sulfo-SMCC and are unusually stable up to pH 7.5 because of the cyclohexane bridge in the spacer arm. |
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