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Sigma-Aldrich

SMPH (succinimidyl-6-((b-maleimidopropionamido)hexanoate)

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Synonym(s):
SMPH, Succinimidyl-6-(beta-maleimidopropionamido)hexanoate
Empirical Formula (Hill Notation):
C17H21N3O7
CAS Number:
Molecular Weight:
379.36
MDL number:
PubChem Substance ID:

Assay

≥90%

Quality Level

form

powder

mol wt

379.36

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

DMSO or DMF: soluble

functional group

NHS ester
maleimide

shipped in

ambient

storage temp.

2-8°C

SMILES string

O=C(CCCCCNC(CCN1C(C=CC1=O)=O)=O)ON2C(CCC2=O)=O

InChI

1S/C17H21N3O7/c21-12(9-11-19-13(22)5-6-14(19)23)18-10-3-1-2-4-17(26)27-20-15(24)7-8-16(20)25/h5-6H,1-4,7-11H2,(H,18,21)

InChI key

WCMOHMXWOOBVMZ-UHFFFAOYSA-N

Related Categories

General description

SMPH is a heterobifunctional crosslinker with 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 the 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 greater than 7.5. For these reasons, conjugation experiments involving this type of heterobifunctional crosslinker 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.

Features and Benefits

  • Reactive groups: NHS ester and maleimide
  • Reactive towards: amino and sulfhydryl groups
  • Slightly longer and more soluble than SMPB
  • NHS ester reacts with primary amines at pH 7-9, forming a stable amide bond
  • Maleimide reacts with -SH groups at pH 6.5-7.5, forming a stable thioether bond
  • Non-cleavable
  • Water-insoluble (dissolve first in DMF or DMSO)

Caution

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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


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Chen, Z., et al.
The Journal of Biological Chemistry, 278, 48348-48356 (2003)

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