2,5-dioxopyrrolidin-1-yl 3-(pyridin-2-yldisulfanyl)propanoate

• ChemBase ID: 104573
• Molecular Formular: C12H12N2O4S2
• Molecular Mass: 312.36468
• Monoisotopic Mass: 312.02384887
• SMILES: O=C(CCSSc1ncccc1)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCSSc1ccccn1
• InChI: InChI=1S/C12H12N2O4S2/c15-10-4-5-11(16)14(10)18-12(17)6-8-19-20-9-3-1-2-7-13-9/h1-3,7H,4-6,8H2
• InChIKey: JWDFQMWEFLOOED-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-(pyridin-2-yldisulfanyl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-(pyridin-2-yldisulfanyl)propanoate
• Synonyms: 3-(2-Pyridyldithio)propionic Acid N-Succinimidyl Ester; N-Succinimidyl 3-(2-pyridyldithio)propionate; 3-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide ester; SPDP; N-Succinimidyl 3-[2-pyridyldithio]-propionate; 3-(2-PYRIDYLDITHIO)-PROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER; N-琥珀酰亚胺-3-(2-吡啶二硫代)丙酸酯; 3-(2-吡啶基二硫基)丙酸N-羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 68181-17-9
• EC Number: 269-034-3
• MDL Number: MFCD00009636
• Beilstein Number: 1548137
• PubChem SID: 162091604; 24898409
• PubChem CID: 100682

CALCULATED PROPERTIES

• Acid pKa: 17.708975
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.3970946
• LogD (pH = 7.4): 1.397537
• Log P: 1.3975426
• Molar Refractivity: 74.2703 cm^3
• Polarizability: 29.894728 Å^3
• Polar Surface Area: 76.57 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble50 mg/mL; Chloroform; DMF: soluble; DMSO
• Apperance: powder; White Solid
• Melting Point: 69-70°C; 84-86 °C(lit.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%; 98%
• Empirical Formula (Hill Notation): C12H12N2O4S2

DETAILS

MP Biomedicals - 02156456

Crystalline
A heterobifunctional cross-linking reagent which incorporates a disulfide bridge between the conjugated species.

Sigma Aldrich - P3415

Application
A heterobifunctional cross-linking reagent with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5). Second coupling specific for molecules containing free sulfhydryl by thiol-disulfide exchange buffered at pH 8.0 (7.5-8.5). Alternately, this reagent may be used as a protected thiolating reagent following initial coupling and reduction of linker. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Incorporates 4 atom linker.
Packaging
25, 100 mg in poly bottle
5 mg in glass bottle

Sigma Aldrich - 287113

Application
Versatile heterofunctional cross-linking agent for proteins and enzymes.1

Toronto Research Chemicals - P996850

A heterobifunctional cross-linker.

REFERENCES

• Carlsson, J., et al., Biochem. J., 173
• Carlsson, J. et al.: Biochem. J., 173, 723 (1978)
• Neurath, A.R., and Strick, N.J.. : J. Virol. Meth., 3, 155 (1981)