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63176

Sigma-Aldrich

6-Maleimidohexanoic acid

≥98.0% (HPLC)

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Synonym(s):
6-Maleimidocaproic acid, N-Maleoyl-6-aminocaproic acid, N-(5-Carboxypentyl)maleimide
Empirical Formula (Hill Notation):
C10H13NO4
CAS Number:
55750-53-3
Molecular Weight:
211.21
Beilstein:
1532405
MDL number:
MFCD00043140
PubChem Substance ID:
329759803
NACRES:
NA.25

Quality Level

200

Assay

≥98.0% (HPLC)

mp

86-91 °C

storage temp.

room temp

SMILES string

OC(=O)CCCCCN1C(=O)C=CC1=O

InChI

1S/C10H13NO4/c12-8-5-6-9(13)11(8)7-3-1-2-4-10(14)15/h5-6H,1-4,7H2,(H,14,15)

InChI key

WOJKKJKETHYEAC-UHFFFAOYSA-N

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Application

6-Maleimidohexanoic acid may be used as a spacer in the construction of drug and other types of bioconjugates. 6-Maleimidohexanoic acid is used with N-hydroxysuccinimide ester as a bifunctional cross-linking reagent.
Probe for thiol groups (SH-groups) in membrane proteins.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H335

Hazard Classifications

Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
Ralph Rahme et al.
Journal of neurosurgery, 121(6), 1354-1358 (2014-09-27)
The role of endovascular therapy in patients with acute ischemic stroke and a solitary M2 occlusion remains unclear. Through a pooled analysis of 3 interventional stroke trials, the authors sought to analyze the impact of successful early reperfusion of M2
Lauren L Jantzie et al.
Cerebral cortex (New York, N.Y. : 1991), 25(2), 482-495 (2013-09-21)
The pathophysiology of perinatal brain injury is multifactorial and involves hypoxia-ischemia (HI) and inflammation. N-methyl-d-aspartate receptors (NMDAR) are present on neurons and glia in immature rodents, and NMDAR antagonists are protective in HI models. To enhance clinical translation of rodent
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
S S Ghosh et al.
Bioconjugate chemistry, 1(1), 71-76 (1990-01-01)
Two general methods which exploit the reactivity of sulfhydryl groups toward maleimides are described for the synthesis of oligonucleotide-enzyme conjugates for use as nonradioisotopic hybridization probes. In the first approach, 6-maleimidohexanoic acid succinimido ester was used to couple 5'-thiolated oligonucleotide
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