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63175

Sigma-Aldrich

4-Maleimidobutyric acid N-hydroxysuccinimide ester

≥98.0% (HPLC)

Synonym(s):

4-Maleimidobutyric acid N-succinimidyl ester, N-(γ-Maleimidobutyryloxy)succinimide, N-Succinimidyl 4-maleimidobutyrate, GMBS

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About This Item

Empirical Formula (Hill Notation):
C12H12N2O6
CAS Number:
80307-12-6
Molecular Weight:
280.23
Beilstein:
6427689
MDL number:
MFCD00036817
UNSPSC Code:
12352106
PubChem Substance ID:
329759802
NACRES:
NA.25

Quality Level

100

Assay

≥98.0% (HPLC)

reaction suitability

reagent type: linker

mp

123-129 °C

functional group

NHS ester

storage temp.

2-8°C

SMILES string

O=C1N(CCCC(ON2C(CCC2=O)=O)=O)C(C=C1)=O

InChI

1S/C12H12N2O6/c15-8-3-4-9(16)13(8)7-1-2-12(19)20-14-10(17)5-6-11(14)18/h3-4H,1-2,5-7H2

InChI key

PVGATNRYUYNBHO-UHFFFAOYSA-N

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Application

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. Provides a 7-atom linker.

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
BCCM0407
BCCM0539
BCBV0406
BCBV3389
SLBH6654

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Jae-Wan Jung et al.
Proteomics, 6(4), 1110-1120 (2006-01-13)
We modified gold arrays with a glutathione (GSH) surface, and investigated high-throughput protein interactions with a spectral surface plasmon resonance (SPR) biosensor. We fabricated the GSH exterior on gold surfaces by successive modification with aminoethanethiol, 4-maleimidobutyric acid N-hydroxysuccinimide ester and
Erdrin Azemi et al.
Acta biomaterialia, 4(5), 1208-1217 (2008-04-19)
Silicon-based implantable neural electrode arrays are known to experience failure during long-term recording, partially due to host tissue responses. Surface modification and immobilization of biomolecules may provide a means to improve their biocompatibility and integration within the host brain tissue.
Tae Hyun Kim et al.
Nature communications, 10(1), 1478-1478 (2019-04-02)
Circulating tumor cells (CTCs) have become an established biomarker for prognosis in patients with various carcinomas. However, current ex vivo CTC isolation technologies rely on small blood volumes from a single venipuncture limiting the number of captured CTCs. This produces
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