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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:
Molecular Weight:
334.32
Beilstein:
1555271
MDL number:
PubChem Substance ID:
NACRES:
NC.07

Quality Level

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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This Item
M979463177P3415
form

powder

form

powder

form

solid

form

powder

reaction suitability

reagent type: linker

reaction suitability

reagent type: linker

reaction suitability

reagent type: linker

reaction suitability

reagent type: cross-linking reagent

mp

180-182 °C (lit.)

mp

70-73 °C (lit.)

mp

67-73 °C, 70-73 °C (lit.)

mp

84-86 °C (lit.)

solubility

chloroform: 50 mg/mL, DMF: soluble

solubility

chloroform: 100 mg/mL, DMF: soluble (lit.)(lit.)

solubility

-

solubility

acetone: 50 mg/mL, DMF: soluble

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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