3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) Chemical Properties

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) Usage And Synthesis

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

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)(57757-57-0)Related Product Information

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