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63177

Sigma-Aldrich

6-Maleimidohexanoic acid N-hydroxysuccinimide ester

≥98.0% (HPLC)

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/REAXYS Number:
1499815
MDL number:
MFCD00043043
UNSPSC Code:
12352106
PubChem Substance ID:
329759804
NACRES:
NA.25

Quality Level

200

assay

≥98.0% (HPLC)

form

solid

reaction suitability

reagent type: linker

mp

67-73 °C
70-73 °C (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

6-Maleimidohexanoic acid N-hydroxysuccinimide ester is a heterobifunctional cross-linking reagent 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). Second coupling 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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Reagent for cross-linking and immobilisation of proteins

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Maleimide-PEG2-succinimidyl ester ≥95%

Sigma-Aldrich

746223

Maleimide-PEG2-succinimidyl ester

T. Kitagawa
Enzyme Immunoassay, 81-81 (1981)
Preparation and characterization of hetero-bifunctional cross-linking reagents for protein modifications.
Kitagawa, T., et al.
Chemical & Pharmaceutical Bulletin, 29, 1130-1130 (1981)
Mitsuko Maeda et al.
Bioorganic & medicinal chemistry letters, 15(3), 621-624 (2005-01-25)
The adenovirus vector is a promising carrier for the efficient transfer of genes into cells via the coxackie-adenovirus receptor (CAR) and integrins (alphavbeta3 and alphavbeta5). The clinical use of the adenovirus vector remains problematic however. Successful administration of this vector
Shinya Kida et al.
Chemical & pharmaceutical bulletin, 55(4), 685-687 (2007-04-06)
6-maleimidohexanoic acid N-hydroxysuccinimide ester has been used widely for preparation of enzyme immunoconjugates as a unique heterobifunctional cross-linking reagent. Its heterobifunctional reactivity is good, but its ester portion hydrolyzes easily in the presence of water. Several 6-maleimidohexanoic acid active esters
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)
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