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M9794

Sigma-Aldrich

6-Maleimidohexanoic acid N-hydroxysuccinimide ester

≥98%, powder

Synonym(s):

6-Maleimidocaproic acid N-succinimidyl ester, N-(ε-Maleimidocaproyloxy)succinimide, N-Succinimidyl 6-maleimidocaproate, EMCS

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About This Item

Empirical Formula (Hill Notation):
C14H16N2O6
CAS Number:
55750-63-5
Molecular Weight:
308.29
Beilstein:
1499815
MDL number:
MFCD00043043
UNSPSC Code:
12352106
PubChem Substance ID:
329818098
NACRES:
NA.25

Quality Level

200

Assay

≥98%

form

powder

reaction suitability

reagent type: linker

mp

70-73 °C (lit.)

solubility

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

functional group

NHS ester

storage temp.

−20°C

SMILES string

O=C(ON(C(CC1)=O)C1=O)CCCCCN2C(C=CC2=O)=O

InChI

1S/C14H16N2O6/c17-10-5-6-11(18)15(10)9-3-1-2-4-14(21)22-16-12(19)7-8-13(16)20/h5-6H,1-4,7-9H2

InChI key

VLARLSIGSPVYHX-UHFFFAOYSA-N

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Application

A heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds 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). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Contains 9 atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H351

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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S Hashida et al.
Journal of applied biochemistry, 6(1-2), 56-63 (1984-02-01)
Nine different maleimide compounds were evaluated for the conjugation of Fab' to horseradish peroxidase through thiol groups in the hinge. The compounds evaluated were succinimidyl maleimidoacetate (I), succinimidyl 4-maleimidobutyrate (II), succinimidyl 6-maleimidohexanoate (III), succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate (IV), succinimidyl m-maleimidobenzoate (V), succinimidyl
Y Nakano et al.
International archives of allergy and immunology, 120(3), 199-208 (1999-12-11)
We have previously reported that ovalbumin (OVA) coupled with liposome via glutaraldehyde (GA) induced OVA-specific- and IgE-selective unresponsiveness in mice. In this study, OVA-liposome conjugates were made using four different coupling protocols: via GA, N-(6-maleimidocaproyloxy) succinimide (EMCS), disuccinimidyl suberate (DSS)
Corinne Stannard et al.
Biochemistry, 42(47), 13909-13918 (2003-11-26)
Posttranslational modifications of the endothelin receptors A and B from human lung fibroblasts were investigated before and after stimulation of the cells with (dA)(30)-5'-S-EMC-endothelin-1. The patterns of phosphorylation and palmitoylation of both receptors were much more complicated than expected. In
C Fargeas et al.
Journal of clinical microbiology, 34(2), 241-248 (1996-02-01)
Synthetic peptides, derived from the amino acid sequence of a Leishmania donovani clone, were used to develop an enzyme-linked immunosorbent assay (ELISA) for detecting antibodies against L. donovani. For this purpose, five peptides were conjugated to a protein carrier, human
N J Maeji et al.
Journal of immunological methods, 146(1), 83-90 (1992-01-21)
Recently, the multipin approach for simultaneous multiple peptide synthesis was applied to the analysis of T cell determinants by using a novel cleavage method (Maeji et al., 1990). A diketopiperazine forming linker allowed cleavage of peptides into aqueous buffer which
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