Skip to Content
Merck
All Photos(2)

Key Documents

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


About This Item

Empirical Formula (Hill Notation):
C16H18N2O6
CAS Number:
Molecular Weight:
334.32
Beilstein:
1555271
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
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

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

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

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)
Matthias Kuhlmann et al.
Molecular therapy. Nucleic acids, 9, 284-293 (2017-12-17)
The long blood circulatory property of human serum albumin, due to engagement with the cellular recycling neonatal Fc receptor (FcRn), is an attractive drug half-life extension enabling technology. This work describes a novel site-specific albumin double-stranded (ds) DNA assembly approach
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

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