M5525

4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester

≥98%, powder

• Synonym(s): N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC
• Empirical Formula (Hill Notation): C₁₆H₁₈N₂O₆
• CAS Number: 64987-85-5
• Molecular Weight: 334.32
• Beilstein/REAXYS Number: 1555271
• MDL number: MFCD00009634
• UNSPSC Code: 12352103
• PubChem Substance ID: 24897020
• NACRES: NC.07

Properties

• assay: ≥98%
• form: powder
• reaction suitability: reagent type: linker
• mp: 180-182 °C (lit.)
• solubility: chloroform: 50 mg/mL; DMF: soluble
• functional group: NHS ester
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: O=C(ON1C(CCC1=O)=O)C2CCC(CN3C(C=CC3=O)=O)CC2
• 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
• InChI key: JJAHTWIKCUJRDK-UHFFFAOYSA-N

Description

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.

Application

4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (SMCC) is useful for the preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. It has been used for the coupling of a peptide sequence to an amino group.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves