Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

M5525

Sigma-Aldrich

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

≥98%, powder

Synonym(s):

N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate, SMCC

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C16H18N2O6
CAS Number:
64987-85-5
Molecular Weight:
334.32
Beilstein/REAXYS Number:
1555271
MDL number:
MFCD00009634
UNSPSC Code:
12352103
PubChem Substance ID:
24897020
NACRES:
NC.07

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ahmed H
Principles and Reactions of Protein Extraction, Purification, and Characterization (2004)
David A Elsemore et al.
Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc, 29(5), 645-653 (2017-04-21)
We report the development and field validation of 2 ELISAs for the detection of Ancylostoma caninum or Toxocara canis coproantigens in the feces of dogs with experimental and natural infections, and evidence of cross-reactivity with respective feline counterparts. A. caninum-specific
Dieke van Dinther et al.
Cancers, 11(2) (2019-02-16)
The lack of tumor-reactive T cells is one reason why immune checkpoint inhibitor therapies still fail in a significant proportion of melanoma patients. A vaccination that induces melanoma-specific T cells could potentially enhance the efficacy of immune checkpoint inhibitors. Here
Functionalization and cellular uptake of boron carbide nanoparticles. The first step toward T cell-guided boron neutron capture therapy.
Mortensen MW
Bioconjugate Chemistry, 17, 284-284 (2006)
Patrick Imesch et al.
Experimental and therapeutic medicine, 6(3), 786-790 (2013-10-19)
Polycationic cell-penetrating peptides (CPPs) deliver macromolecules into cells without losing the functional properties of the cargoed macromolecule. The aim of this study was to determine whether exogenous cytochrome
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service