SMPH (succinimidyl-6-((b-maleimidopropionamido)hexanoate)
ALDRICH/803626
Synonym: SMPH; Succinimidyl-
CAS Number: 367927-39-7
Empirical Formula (Hill Notation): C17H21N3O7
Molecular Weight: 379.36
MDL Number: MFCD01863460
Linear Formula: C17H21N3O7
Product Type: Chemical
| assay | ≥90% |
| form | powder |
| functional group | maleimide |
| NHS ester | |
| InChI | 1S/C17H21N3O7/c21-12(9-11 |
| InChI key | WCMOHMXWOOBVMZ-UHFFFAOYSA |
| mol wt | 379.36 |
| Quality Level | 100  |
| reaction suitability | reagent type: cross-linking reagent |
| shipped in | ambient |
| SMILES string | O=C(CCCCCNC(CCN1C(C=CC1=O |
| solubility | DMSO or DMF: soluble |
| storage condition | desiccated |
| storage temp. | 2-8°C |
| 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. |
| 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) |
| 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. |
| Symbol |  GHS07 |
| Signal word | Warning |
| Hazard statements | H315 - H319 - H335 |
| Precautionary statements | P302 + P352 - P305 + P351 + P338 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥90% |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352106 |