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M5525

Sigma-Aldrich

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

≥98%, powder

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

Quality Level

200

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

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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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