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63179

Sigma-Aldrich

3-(Maleimido)propionic acid N-hydroxysuccinimide ester

≥98.5% (HPLC)

Synonym(s):

3-(Maleimido)propionic acid N-succinimidyl ester, BMPS, N-(3-Maleimidopropionyloxy)succinimide, N-Maleoyl-β-alanine N′-hydroxysuccinimide ester, N-Succinimidyl 3-maleimidopropionate

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About This Item

Empirical Formula (Hill Notation):
C11H10N2O6
CAS Number:
55750-62-4
Molecular Weight:
266.21
Beilstein:
1492578
MDL number:
MFCD00043141
UNSPSC Code:
12352106
PubChem Substance ID:
329759806
NACRES:
NA.25

Quality Level

200

Assay

≥98.5% (HPLC)

form

solid

reaction suitability

reagent type: linker

mp

167-171 °C

functional group

NHS ester

storage temp.

2-8°C

SMILES string

O=C1CCC(N1OC(CCN2C(C=CC2=O)=O)=O)=O

InChI

1S/C11H10N2O6/c14-7-1-2-8(15)12(7)6-5-11(18)19-13-9(16)3-4-10(13)17/h1-2H,3-6H2

InChI key

JKHVDAUOODACDU-UHFFFAOYSA-N

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Application

Succinimidyl 3-maleimidopropionate (SMP, BMPS) is used as an aliphatic heterobifunctional crosslinker reagent. It is used for techniques such as the cross-linking of haptens to enzymes prior to enzyme immunoassays or fluorogenic substrates to peptidic antigens for use in fluorescence immunoassays.

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
BCBW7244
SLCK8393
SLCK8423
SLCK8405
SLCK8387

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S J Xiao et al.
Journal of materials science. Materials in medicine, 8(12), 867-872 (2004-09-07)
Surface modification of acid-pretreated titanium with 3-aminopropyltriethoxylsilane (APTES) in dry toluene resulted in covalently bonded siloxane films with surface coverage that was relatively controllable by regulating the reaction conditions. A hetero-bifunctional cross-linker, N-succinimidyl-3-maleimidopropionate (SMP), reacted with the terminal amino groups
T. Kitagawa
Enzyme Immunoassay, 81-81 (1981)
S Heyse et al.
Protein science : a publication of the Protein Society, 4(12), 2532-2544 (1995-12-01)
A new method is presented for measuring sensitively the interactions between ligands and their membrane-bound receptors in situ using integrated optics, thus avoiding the need for additional labels. Phospholipid bilayers were attached covalently to waveguides by a novel protocol, which
M C Durrieu et al.
Journal of materials science. Materials in medicine, 15(7), 779-786 (2004-09-28)
Ceramics possess osteoconductive properties but exhibit no intrinsic osteoinductive capacity. Consequently, they are unable to induce new bone formation in extra osseous sites. In order to develop bone substitutes with osteogenic properties, one promising approach consists of creating hybrid materials
Wuensch, E.
Hoppe-Seyler'S Zeitschrift fur Physiologische Chemie, 366, 53-53 (1985)
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