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M8759

Sigma-Aldrich

3-Maleimidobenzoic acid N-hydroxysuccinimide ester

Synonym(s):

MBS

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About This Item

Empirical Formula (Hill Notation):
C15H10N2O6
CAS Number:
58626-38-3
Molecular Weight:
314.25
Beilstein:
1505254
EC Number:
261-368-8
MDL number:
MFCD00005514
UNSPSC Code:
47101511
PubChem Substance ID:
24897286

mp

175-177 °C (lit.)

solubility

ethyl acetate or DMF: ≤20 mg/mL (may require addition of solvent to coupling buffer to at least 5% to maintain solubility)

storage temp.

−20°C

SMILES string

O=C1CCC(N1OC(C2=CC=CC(N3C(C=CC3=O)=O)=C2)=O)=O

InChI

1S/C15H10N2O6/c18-11-4-5-12(19)16(11)10-3-1-2-9(8-10)15(22)23-17-13(20)6-7-14(17)21/h1-5,8H,6-7H2

InChI key

LLXVXPPXELIDGQ-UHFFFAOYSA-N

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Application

Heterobifunctional crosslinking reagent reactive toward primary amine and sulfhydryl. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.0, followed by coupling to compounds containing sulfhydryl by thioether at same pH. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.

Other Notes

The aryl maleimide is less stable than alkyl maleimide linkers.

replaced by

Product No.
Description
Pricing

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D M Grieger et al.
Journal of animal science, 68(11), 3747-3754 (1990-11-01)
This study evaluated the antigenicity of LH-ovalbumin complexes produced using different conjugation techniques. Two homobifunctional cross-linkers, glutaraldehyde (Glut) and carbodiimide (ECDI), were evaluated together with one heterobifunctional reagent, m-maleimido-benzoyl N-hydroxysuccinimide ester (MBS). Polyacrylamide gel electrophoresis and Western transfer techniques were
Takayuki Miyanishi et al.
Biochemistry, 41(17), 5429-5438 (2002-04-24)
In the presence of myosin S1 or myosin heads, actin filaments tend to form bundles. The biological meaning of the bundling of actin filaments has been unclear. In this study, we found that the cardiac myosin heads can form the
M Tomita et al.
Biochimica et biophysica acta, 1055(3), 199-206 (1990-12-10)
Methods for pre-selecting B lymphocytes were studied and investigated. First, biotinylated antigen was used for selecting B lymphocytes. These pre-selected B lymphocytes were then combined with biotinylated myeloma cells by adding streptavidin. The final formula of the selected B cell-myeloma
D Heintz et al.
FEBS letters, 329(1-2), 9-12 (1993-08-23)
By reacting trimethylammoniobromobimane bromide (TMB bromide) with rabbit muscle actin, a fluorescent reporter group was linked to cysteine at position 374. Fluorescence of TMB-actin decreased significantly on addition of thymosin beta 4 (T beta 4), a peptide of 43 amino
M Miki et al.
Biochemistry, 30(22), 5625-5630 (1991-06-04)
A chemical modification of G-actin with (m-maleimidobenzoyl)-N-hydroxysuccinimide ester (MBS) impairs actin polymerization [Bettache, N., Bertrand, R., & Kassab, R. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 6028-6032]. MBS-actin recovers the ability to polymerize when a 2-fold molar excess of phalloidin
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