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M5525

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

Name: 4-(<I>N</I>-Maleimidomethyl)cyclohexanecarboxylic acid <I>N</I>-hydroxysuccinimide ester
Brand: SIGMA

≥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

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Properties

Quality Segment

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

Description

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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