803626
SMPH (succinimidyl-6-((b-maleimidopropionamido)hexanoate)
Synonym(s):
SMPH, Succinimidyl-6-(beta-maleimidopropionamido)hexanoate
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About This Item
Empirical Formula (Hill Notation):
C17H21N3O7
CAS Number:
Molecular Weight:
379.36
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22
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
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.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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