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568600

Sigma-Aldrich

6-Maleimidohexanoic acid N-hydroxysuccinimide ester

98%

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:
12352100
PubChem Substance ID:
24880215
NACRES:
NA.22

Quality Level

100

Assay

98%

reaction suitability

reagent type: cross-linking reagent

mp

70-73 °C (lit.)

functional group

NHS ester
imide
maleimide

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 can be used in:
  • Synthesis of maleimide-activated carbohydrates for site-specific glycosylation of cysteine-containing peptides and proteins via maleimide-thiol ligation reaction.
  • Synthesis of a glucuronide prodrug of doxorubicin bearing a maleimide side chain as an antitumor agent.
  • Cross-linking oligonucleotides with the amino groups on the substrate to fabricate DNA microarrays.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBZ3468V
MKBL7769V
MKBR7741V
MKBH3139V
MKBH6545V

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Microarray fabrication with covalent attachment of DNA using bubble jet technology.
Okamoto T, et al.
Nature Biotechnology, 18(4), 438-438 (2000)
Synthesis and antitumor efficacy of a β-glucuronidase-responsive albumin-binding prodrug of doxorubicin.
Legigan T, et al.
Journal of Medicinal Chemistry, 55(9), 4516-4520 (2012)
Synthesis of maleimide-activated carbohydrates as chemoselective tags for site-specific glycosylation of peptides and proteins.
Ni J, et al.
Bioconjugate Chemistry, 14(1), 232-238 (2003)
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)
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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