≥90% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
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.
Features and advantages:
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
| Canonical Smiles | C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCSSC2=CC=CC=N2 |
|---|---|
| IUPAC Name | (2,5-dioxopyrrolidin-1-yl) 6-[3-(pyridin-2-yldisulfanyl)propanoylamino]hexanoate |
| InChIKey | QYEAAMBIUQLHFQ-UHFFFAOYSA-N |
| INCHI | 1S/C18H23N3O5S2/c22-14(10-13-27-28-15-6-3-5-12-20-15)19-11-4-1-2-7-18(25)26-21-16(23)8-9-17(21)24/h3,5-6,12H,1-2,4,7-11,13H2,(H,19,22) |
| Isomeric SMILES | C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCSSC2=CC=CC=N2 |
| PubChem CID | 157808 |
| Molecular Weight | 425.52 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridines and derivatives |
| Alternative Parents | Pyrrolidine-2-ones Dicarboximides Heteroaromatic compounds Carboxylic acid salts Secondary carboxylic acid amides Lactams Organic disulfides Sulfenyl compounds Monocarboxylic acids and derivatives Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides Organic salts Organonitrogen compounds Organopnictogen compounds |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyridine - Pyrrolidone - 2-pyrrolidone - Dicarboximide - Pyrrolidine - Heteroaromatic compound - Carboxamide group - Carboxylic acid salt - Lactam - Organic disulfide - Secondary carboxylic acid amide - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Sulfenyl compound - Azacycle - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic salt - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 E2517065 | Certificate of Analysis | Jul 08, 2024 | S595683 |
| G2415737 | Certificate of Analysis | Jul 08, 2024 | S595683 |
| G2415738 | Certificate of Analysis | Jul 08, 2024 | S595683 |
| G2415739 | Certificate of Analysis | Jul 08, 2024 | S595683 |
| I2517068 | Certificate of Analysis | Jul 08, 2024 | S595683 |
| Sensitivity | Moisture Sensitive |
|---|---|
| Melt Point(°C) | 92-94°C (lit.) |
| Molecular Weight | 425.500 g/mol |
| XLogP3 | 1.000 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 13 |
| Exact Mass | 425.108 Da |
| Monoisotopic Mass | 425.108 Da |
| Topological Polar Surface Area | 156.000 Ų |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Complexity | 545.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
