M5525

4-(N-Maleimidomethyl)cyclohexan-Carboxylsäure N-hydroxysuccinimid-Ester

≥98%, powder

• Synonym(e): N-Succinimidyl-4-(maleinimidomethyl)-cyclohexancarboxylat, SMCC
• Empirische Formel (Hill-System): C₁₆H₁₈N₂O₆
• CAS-Nummer: 64987-85-5
• Molekulargewicht: 334.32
• Beilstein: 1555271
• MDL-Nummer: MFCD00009634
• UNSPSC-Code: 12352103
• PubChem Substanz-ID: 24897020
• NACRES: NC.07

Eigenschaften

• Assay: ≥98%
• Form: powder
• Eignung der Reaktion: reagent type: linker
• mp (Schmelzpunkt): 180-182 °C (lit.)
• Löslichkeit: chloroform: 50 mg/mL; DMF: soluble
• Funktionelle Gruppe: NHS ester
• Versandbedingung: wet ice
• Lagertemp.: −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
• InChIKey: JJAHTWIKCUJRDK-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves