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| | 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) Basic information |
| Product Name: | 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) | | Synonyms: | 3,3'-dithiopropionic acid bis(N-hydroxysuccinimide ester);Di(N-succinimidyl) 3,3μ-dithiodipropionate, Dithiobis(succinimidyl propionate), DTSP, Lomants reagent;3,3'-DITHIODIPROPIONIC ACID BIS(N-SUCCINIMIDYL ESTER);3,3'-DITHIO-BIS(PROPIONIC ACID N-HYDROXYSUCCINIMIDE ESTER);3,3'-DITHIOBIS(SUCCINIMIDYL PROPIONATE);3,3'-DITHIOPROPIONIC ACID DI(N-SUCCINIMIDYL ESTER);3,3'-DITHIODIPROPIONIC ACID DI-(N-HYDROXY-SUCCINIMIDE ESTER);DSS, WATER-SOLUBLE | | CAS: | 57757-57-0 | | MF: | C14H16N2O8S2 | | MW: | 404.42 | | EINECS: | 260-931-5 | | Product Categories: | N-Substituted Maleimides, Succinimides & Phthalimides;Heterocycles;Sulfur & Selenium Compounds;Homobifunctional Crosslinker;homoXlink;N-Substituted Succinimides;ADC LINKER | | Mol File: | 57757-57-0.mol |  |
| | 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) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | 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 |
| | 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`-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. | | Uses | 3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester) (DSP) has been used as a protein cross-linker. | | 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) Preparation Products And Raw materials |
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