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43780

Sigma-Aldrich

Dimethyl 3,3′-dithiopropionimidate dihydrochloride

purum, ≥95.0% (AT)

Synonyme(s) :

DTBP, Dimethyl 3,3′-dithio-bis(propionimidate) dihydrochloride, Wang/Richards’ reagent

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About This Item

Formule empirique (notation de Hill) :
C8H16N2O2S2 · 2HCl
Numéro CAS:
38285-78-8
Poids moléculaire :
309.28
Numéro MDL:
MFCD00043245
Code UNSPSC :
12352000
ID de substance PubChem :
24867398

Qualité

purum

Essai

≥95.0% (AT)

Température de stockage

2-8°C

Chaîne SMILES 

Cl.Cl.COC(=N)CCSSCCC(=N)OC

InChI

1S/C8H16N2O2S2.2ClH/c1-11-7(9)3-5-13-14-6-4-8(10)12-2;;/h9-10H,3-6H2,1-2H3;2*1H

Clé InChI

CQBCVFHLZAVNPF-UHFFFAOYSA-N

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Application

A homobifunctional, cleavable cross-linking reagent. Typically, reacted with primary amines in the pH range 7.0-10.0 to form amidine bonds.
Reactant for:
  • Synthesis of glutathione-sensitive cross-linked polyethylenimine gene vector
  • Preparation of cyclodextrin-containing polymers designed for gene delivery
  • Crosslinking of chick oviduct progesterone-receptor subunits

Attention

The reagant is readily hydrolyzed at neutral pH. Avoid use of reducing agents during coupling reactions.

Remarque sur l'analyse

product decomposes at 111-115°C, residual melts at 160-164°C

Autres remarques

Note that the amidine linkage preserves original primary amine positive charge. The disulfide linkage is cleavable by mild reduction. Incorporates an eight atom linker.
Cleavable bifunctional reagent used for cross-linking of membrane proteins and hemoglobin; For the preparation of an activated solid support; Cross-linking of a cytochrome oxidase complex

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Réf. du produit
Description
Tarif

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315

Classification des risques

Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number

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Consulter la Bibliothèque de documents

K Wang et al.
The Journal of biological chemistry, 250(16), 6622-6626 (1975-08-25)
Dimethyl-3,3'-dithiobispropionimidate penetrates intact human erythrocytes and cross-links many of the membrane proteins to hemoglobin as well as to each other. The cross-linked complexes so produced have been analyzed by both one- and two-dimensional sodium dodecyl sulfate polyacrylamide gel electrophoresis, making
Isolation of human erythrocyte membranes and their outer surface proteins by covalent fractionation on solid support.
Y Eshdat et al.
FEBS letters, 101(1), 43-46 (1979-05-01)
V L Chashchin et al.
Biochimica et biophysica acta, 828(3), 313-324 (1985-04-29)
A cleavable cross-linking reagent, dimethyl-3,3'-dithiobispropionimidate, was used to study the molecular organization of adrenocortical cytochrome P-450scc. Extensive cross-linking was found to occur, resulting in the formation of heterologous oligomers up to octamer. The covalently cross-linked complex of adrenocortical cytochrome P-450scc
D A Gillespie et al.
Molecular and cellular biology, 9(2), 865-868 (1989-02-01)
A single nuclear protein (Myc-associated protein) can be specifically cross-linked to avian Myc proteins by treatment of nuclei or cells with the reversible cross-linker dimethyl 3,3'-dithiobis-propionimidate. Myc-associated protein has a molecular weight of approximately 500,000, is not detectably phosphorylated and
R H Xiang et al.
The Journal of biological chemistry, 264(18), 10542-10546 (1989-06-25)
Protein-protein cross-linking was used to determine the spatial arrangement of proteins within the 60 S ribosomal subunits of Saccharomyces cerevisiae. Protein cross-links were generated by treatment of intact ribosomal subunits with dimethyl 3,3'-dithiobispropionimidate. Proteins were extracted from the treated subunits
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