LC-SPDP (succinimidyl 6-[3(2-pyridyldithio)propionamido]hexanoate)
ALDRICH/803642
Synonym: Long chain-SPDP; N-
CAS Number: 158913-22-5
Empirical Formula (Hill Notation): C18 H23 O5 N3 S2
Molecular Weight: 425.52
MDL Number: MFCD00083163
Linear Formula: C18 H23 O5 N3 S2
Product Type: Chemical
| assay | ≥95% |
| form | powder |
| functional group | NHS ester |
| InChI | 1S/C18H23N3O5S2/c22-14(10 |
| InChI key | QYEAAMBIUQLHFQ-UHFFFAOYSA |
| mol wt | 425.52 |
| Quality Level | 100  |
| reaction suitability | reagent type: cross-linking reagent |
| shipped in | ambient |
| SMILES string | O=C1CCC(N1OC(CCCCCNC(CCSS |
| 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 pyridyldithiol • Reactive towards: amino and sulfhydryl groups • Releases a detectable by-product when reacted with a free sulfhydryl group; by measuring the release of pyridine-2-thione at 343 nm, the reaction can be easily followed • Disulfide bond in the spacer arm is readily cleaved by 10-50 mM DTT or TCEP at pH 8.5 • Spacer arm is also easily cleaved using reducing SDS-PAGE sample loading buffer • Cleavable crosslinker allows separation of crosslinked products • Water-insoluble (dissolve first in DMF or DMSO) • SPDP crosslinker is membrane permeable, so crosslinking can be done inside the cells • Compare to other varieties of SPDP-type reagents, including pegylated forms |
| General description: | The amine-reactive portion of SPDP reagents is the N-hydroxysuccinimide (NHS) ester. Reactions are most commonly performed in phosphate, carbonate/bicarbonate, or borate buffers at pH 7-8. Other buffers can be used provided they do not contain primary amines (or thiols or disulfide reducing reagents – see discussion of the sulfhydryl reactivity). The rate of reaction and degradation by hydrolysis increases with increasing pH; for example, the half-life of the NHS ester is several hours at pH 7 and less than 10 minutes at pH 9. NHS-ester reagents like SPDP and LC-SPDP have limited aqueous solubility and must be dissolved in organic solvent before adding them to a reaction mixture. Sulfo-NHS-ester reagents like Sulfo-LC-SPDP are water-soluble and can be added directly to aqueous reaction mixtures. |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥95% |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352200 |