LC-SMCC (succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxy-(6-amidocaproate))
ALDRICH/803383
Empirical Formula (Hill Notation): C22H29N3O7
Molecular Weight: 447.48
MDL Number: MFCD01863459
Linear Formula: C22H29N3O7
Product Type: Chemical
| assay | ≥90% |
| form | powder |
| functional group | maleimide |
| NHS ester | |
| InChI | 1S/C22H29N3O7/c26-17-9-10 |
| InChI key | IHVODYOQUSEYJJ-UHFFFAOYSA |
| mol wt | 447.48 |
| Quality Level | 100  |
| reaction suitability | reagent type: cross-linking reagent |
| shipped in | ambient |
| SMILES string | O=C(CCC1=O)N1OC(CCCCCNC(C |
| 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 toward: amino and sulfhydryl groups • Long-chain variety of SMCC • High purity, crystalline reagent can be used to create high-purity maleimide-activated derivatives • Non-cleavable • Water-insoluble (dissolve first in DMF or DMSO) • Cyclohexane bridge confers added stability to the maleimide group making LC-SMCC an ideal crosslinking agent for maleimide activation of proteins. Maleimide groups are stable for 64 hours in 0.1 M sodium phosphate buffer, pH 7 at 4°C. |
| General description: | LC-SMCC 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 |
| 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 |