| Identification | More | [Name]
3,3'-DITHIODIPROPIONIC ACID DI(N-SUCCINIMIDYL ESTER) | [CAS]
57757-57-0 | [Synonyms]
3,3'-DITHIO-BIS(PROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER)
3,3'-DITHIOBIS(SUCCINIMIDYL PROPIONATE)
3,3'-DITHIODIPROPIONIC ACID BIS(N-SUCCINIMIDYL ESTER)
3,3'-DITHIODIPROPIONIC ACID DI-(N-HYDROXY-SUCCINIMIDE ESTER)
3,3'-DITHIODIPROPIONIC ACID DI(N-SUCCINIMIDYL ESTER)
3,3'-DITHIOPROPIONIC ACID DI(N-SUCCINIMIDYL ESTER)
DI(N-SUCCINIMIDYL) 3,3'-DITHIODIPROPIONATE
(DISULFOSUCCINIMIDYL)SUBERATE
DITHIOBIS(SUCCINIMIDYL PROPIONATE)
DSP
DSS, WATER-SOLUBLE
DTSP
LOMANTS REAGENT
LOMANT'S REAGENT
SULFO-DSS
3,3-dithio-bis(propionic acid N-*hydroxysuccinim
disuccinimido dithiobispropionate
3,3'-DITHIO-BIS(PROPIONIC ACID N-HYDROXY SUCCINIMID
3,3-DITHIODIPROPIONIC ACID DI(N-SUCCINIMIDYL ESTER)[CROSS-LINKING REAGENT] 98+%
Dithio-bis-succinimidyl propionate (Lomant''s Reagent) | [EINECS(EC#)]
260-931-5 | [Molecular Formula]
C14H16N2O8S2 | [MDL Number]
MFCD00042045 | [Molecular Weight]
404.42 | [MOL File]
57757-57-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
128-133 °C | [Boiling point ]
560.1±60.0 °C(Predicted) | [density ]
1.57±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29309090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 as amine reactive homobifunctional cross-linking reagent, cleavable under mild conditions with hydroxylamine (pH 8.5, 3-6 h, 37oC)
| [Uses]
3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) can be used in the crosslinking of intracellular proteins prior to cell lysis.
| [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 |
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