N-Succinimidyl 3-(2-pyridyldithio)propionate

Base Information

• Chemical Name: N-Succinimidyl 3-(2-pyridyldithio)propionate
• CAS No.: 68181-17-9
• Molecular Formula: C12H12N2O4S2
• Molecular Weight: 312.37
• Hs Code.: 29333990
• European Community (EC) Number: 269-034-3
• NSC Number: 677449,344485
• UNII: 2OHG8V08NL
• DSSTox Substance ID: DTXSID60218366
• Nikkaji Number: J317.385B
• Wikidata: Q27255230
• Mol file: 68181-17-9.mol

Synonyms:N-succinilimidyl 3-(2-pyridylthio)propionate;N-succinimidyl 3-(2-pyridyldithio)propionate;SIPDTP;SPDP

Chemical Property of N-Succinimidyl 3-(2-pyridyldithio)propionate

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 7.42E-09mmHg at 25°C
• Melting Point: 84-86 °C(lit.)
• Refractive Index: 1.649
• Boiling Point: 465.9 °C at 760 mmHg
• PKA: 1.76±0.19(Predicted)
• Flash Point: 235.5 °C
• PSA: 127.17000
• Density: 1.48 g/cm³
• LogP: 1.75710
• Storage Temp.: −20°C
• Solubility.: acetone: 50 mg/mL
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 312.02384922
• Heavy Atom Count: 20
• Complexity: 376

Purity/Quality:

99% ^*data from raw suppliers

SPDP Crosslinker ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCSSC2=CC=CC=N2
• Description: SPDP NHS ester is a heterobiofunctional crosslinker which can react with amine and sulfhydryl groups. SPDP NHS esters are membrane permeable therefore allowing them to funtion inside of cells.
• Uses: Important crosslinking reagent for the preparation of protein-protein and peptide-protein conjugates linked by disulfide bonds. 3-(2-Pyridyldithio)propionic acid N-hydroxysuccinimide ester (SPDP) is useful for the preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.It has been used for antibody conjugation and as a protein cross-linker. A heterobifunctional cross-linker

Technology Process of N-Succinimidyl 3-(2-pyridyldithio)propionate

There total 8 articles about N-Succinimidyl 3-(2-pyridyldithio)propionate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-(2-pyridyldithio)propionic acid (68617-64-1) → N-succinimydyl 3-(2-pyridyldithio)propionate (68181-17-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/anie.201605992

Reference yield: 75.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-(2-pyridylthio)propionic acid hydrochloride (119023-08-4) → N-succinimydyl 3-(2-pyridyldithio)propionate (68181-17-9)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; -40 deg C to -5 deg C, 0 deg C, overnight;

Reference yield:

2,2'-dipyridyldisulphide (2127-03-9) → N-succinimydyl 3-(2-pyridyldithio)propionate (68181-17-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / AcOH / ethanol / 2 h / 20 °C

2: 79 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h / 20 °C

With acetic acid; dicyclohexyl-carbodiimide; In ethanol; dichloromethane;

DOI:10.1021/ja0689029

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

3-(2-pyridyldithio)propionic acid

3-(2-pyridylthio)propionic acid hydrochloride

2,2'-dipyridyldisulphide

Downstream raw materials:

5-<3-<<<<2-<2-pyridyldithio>ethyl>amino>ethyl>amino>-3-oxopropyl>-5'-O-DMT-2'-deoxyuridine

Refernces

• 1、 Liu, Yuanyuan,Zhou, Zhou,Lin, Xi,Xiong, Xiaofeng,Zhou, Rui,Zhou, Minglu,Huang, Yuan. "Enhanced Reactive Oxygen Species Generation by Mitochondria Targeting of Anticancer Drug to Overcome Tumor Multidrug Resistance". . p. 3755 - 3766. Retrieved 2019.
• 2、 -. "NUCLEOSIDE ANALOGUE, PREPARATION METHOD AND APPLICATION". Paragraph 0157; 0158; 0193. . Retrieved 2020/09/22.
• 3、 Suma, Tomoya,Cui, Jiwei,Müllner, Markus,Fu, Shiwei,Tran, Jenny,Noi, Ka Fung,Ju, Yi,Caruso, Frank. "Modulated Fragmentation of Proapoptotic Peptide Nanoparticles Regulates Cytotoxicity". supporting information. p. 4009 - 4018. Retrieved 2017/03/31.