M5525
4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester
≥98%, powder
Synonym(s):
N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC
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About This Item
Empirical Formula (Hill Notation):
C16H18N2O6
CAS Number:
Molecular Weight:
334.32
UNSPSC Code:
12352103
NACRES:
NC.07
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1555271
Assay:
≥98%
Form:
powder
Quality Segment
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
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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