3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester)
- Product Name
- 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester)
- CAS No.
- 57757-57-0
- Chemical Name
- 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester)
- Synonyms
- DSP;DTSP;SULFO-DSS;NSC 328386;LOMANTS REAGENT;DSP Crosslinker;LOMANT'S REAGENT;DSS, WATER-SOLUBLE;(DISULFOSUCCINIMIDYL)SUBERATE;3,3′-Dithiodipropionic acid di
- CBNumber
- CB7251791
- Molecular Formula
- C14H16N2O8S2
- Formula Weight
- 404.42
- MOL File
- 57757-57-0.mol
3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) Property
- Melting point:
- 128-133 °C
- Boiling point:
- 560.1±60.0 °C(Predicted)
- Density
- 1.57±0.1 g/cm3(Predicted)
- storage temp.
- -20°C
- solubility
- chloroform: 50 mg/mL
- form
- powder
- color
- Off-White
- Appearance
- White solid
- BRN
- 1518074
- InChI
- InChI=1S/C14H16N2O8S2/c17-9-1-2-10(18)15(9)23-13(21)5-7-25-26-8-6-14(22)24-16-11(19)3-4-12(16)20/h1-8H2
- InChIKey
- FXYPGCIGRDZWNR-UHFFFAOYSA-N
- SMILES
- S(CCC(ON1C(=O)CCC1=O)=O)SCCC(ON1C(=O)CCC1=O)=O
- CAS DataBase Reference
- 57757-57-0(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D3669
- Product name
- 3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester)
- Purity
- powder
- Packaging
- 500mg
- Price
- $235
- Updated
- 2025/07/31
- Product number
- D3669
- Product name
- 3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester)
- Purity
- powder
- Packaging
- 1g
- Price
- $429
- Updated
- 2025/07/31
- Product number
- D2473
- Product name
- Di(N-succinimidyl) 3,3'-Dithiodipropionate [Cross-linking Reagent]
- Purity
- >97.0%(N)
- Packaging
- 1g
- Price
- $311
- Updated
- 2025/07/31
- Product number
- D2473
- Product name
- Di(N-succinimidyl) 3,3'-Dithiodipropionate [Cross-linking Reagent]
- Purity
- >97.0%(N)
- Packaging
- 5g
- Price
- $864
- Updated
- 2025/07/31
- Product number
- D2473
- Product name
- Di(N-succinimidyl) 3,3'-Dithiodipropionate [Cross-linking Reagent]
- Purity
- >97.0%(N)
- Packaging
- 200mg
- Price
- $100
- Updated
- 2025/07/31
3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) Chemical Properties,Usage,Production
Description
DSP Crosslinker is a cleavable crosslinker. It contains two terminal NHS ester moieties which can react with primary amines. The disulfide bonds can be cleaved via a reduction reaction using Dithiothreitol (DTT) reagent.
Chemical Properties
Off-White Solid
Uses
3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester) (DSP) has been used as a protein cross-linker.
Uses
3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) can be used in the crosslinking of intracellular proteins prior to cell lysis.
Uses
3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) can be used as amine reactive homobifunctional cross-linking reagent, cleavable under mild conditions with hydroxylamine (pH 8.5, 3-6 h, 37oC)
General Description
3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester) (DSP) is a homobifunctional cross-linking reagent containing a cleavable disulfide linkage. It is typically coupled to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5).
reaction suitability
reagent type: cross-linking reagent
Synthesis
6066-82-6
1119-62-6
57757-57-0
General procedure for the synthesis of bis(N-hydroxysuccinimide ester) 3,3'-dithiobispropionic acid from 3,3'-dithiobispropionic acid and N-hydroxysuccinimide: To a solution of dichloromethane (20 mL) containing 3,3'-dithiobispropionic acid (1 g, 4.75 mmol) was added sequentially 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride ( WSC) (2.16 g, 10.5 mmol) and N-hydroxysuccinimide (1.21 g, 10.5 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the solution was concentrated by vacuum to remove the solvent and the obtained residue was purified by silica column chromatography (eluent ratio ethyl acetate/hexane = 1:5) to give the final target product 3,3'-dithiodipropionic acid bis(N-hydroxybutanediimide ester) (1.63 g, 85% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz) and FAB mass spectrometry: 1H NMR δ 3.16 (m, 8H), 2.82 (s, 8H); FAB mass spectrometry (DMSO-d6) [(M+H)+] calculated value of 405, measured value 405.
References
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 96 - 100
[2] Organic and Biomolecular Chemistry, 2005, vol. 3, # 12, p. 2255 - 2261
[3] Patent: CN105315191, 2016, A. Location in patent: Paragraph 0021; 0022; 0023
[4] Patent: US7074766, 2006, B1. Location in patent: Page/Page column 44
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 26, p. 4405 - 4408
3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) manufacturers
- Product
- 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) 57757-57-0
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10
- Product
- 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) 57757-57-0
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-08
- Product
- 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) 57757-57-0
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200kg
- Release date
- 2019-12-26