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Merck
CN

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:
64987-85-5
Molecular Weight:
334.32
UNSPSC Code:
12352103
NACRES:
NC.07
PubChem Substance ID:
24897020
MDL number:
MFCD00009634
Beilstein/REAXYS Number:
1555271
Assay:
≥98%
Form:
powder

Key Documents

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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

SMILES string

O=C(ON1C(CCC1=O)=O)C2CCC(CN3C(C=CC3=O)=O)CC2

InChI key

JJAHTWIKCUJRDK-UHFFFAOYSA-N

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

Quality Level

200

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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.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000527629
0000527628
0000527630
0000527628
0000527629

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