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Merck

803243

Sigma-Aldrich

Sulfo-SMPB (sulfosuccinimidyl 4-(N-maleimidophenyl)butyrate)

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About This Item

Wzór empiryczny (zapis Hilla):
C18H15N2O9SNa
Masa cząsteczkowa:
458.37
Numer MDL:
Kod UNSPSC:
12352200
Identyfikator substancji w PubChem:
NACRES:
NA.22

Postać

powder

Poziom jakości

masa cząsteczkowa

458.38

przydatność reakcji

reagent type: cross-linking reagent

warunki przechowywania

desiccated

rozpuszczalność

water: soluble

grupa funkcyjna

maleimide

Warunki transportu

ambient

temp. przechowywania

−20°C

ciąg SMILES

O=C1CC(S(=O)([O-])=O)C(N1OC(CCCC2=CC=C(N3C(C=CC3=O)=O)C=C2)=O)=O.[Na+]

InChI

1S/C18H16N2O9S.Na/c21-14-8-9-15(22)19(14)12-6-4-11(5-7-12)2-1-3-17(24)29-20-16(23)10-13(18(20)25)30(26,27)28;/h4-9,13H,1-3,10H2,(H,26,27,28);/q;+1/p-1

Klucz InChI

LSZBIKKARBHBPA-UHFFFAOYSA-M

Opis ogólny

SMPB and its water-soluble analog Sulfo-SMPB are heterobifunctional crosslinkers that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. NHS esters react with primary amines at pH 7-9 to form amide bonds, while maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. In aqueous solutions, hydrolytic degradation of the NHS ester is a competing reaction whose rate increases with pH. The maleimide group is more stable than the NHS-ester group but will slowly hydrolyze and also lose its reaction specificity for sulfhydryls at pH values > 7.5. For these reasons, conjugation experiments involving these crosslinkers are usually performed at pH 7.2-7.5, with the NHS-ester (amine-targeted) reaction being accomplished before or simultaneous with the maleimide (sulfhydryl-targeted) reaction.

Cechy i korzyści

  • Reactive groups: sulfo-NHS ester and maleimide
  • Reactive towards: amino and sulfhydryl groups
  • Extended chain length limits steric hindrance
  • Non-cleavable
  • Water-soluble (compare to SMPB)
  • Membrane impermeable, allowing for cell surface labeling

Przestroga

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.
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Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable


Certyfikaty analizy (CoA)

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