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43780

Sigma-Aldrich

Dimethyl 3,3′-dithiopropionimidate dihydrochloride

purum, ≥95.0% (AT)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H16N2O2S2 · 2HCl
CAS Number:
38285-78-8
Molecular Weight:
309.28
MDL number:
MFCD00043245
UNSPSC Code:
12352000
PubChem Substance ID:
24867398

grade

purum

Assay

≥95.0% (AT)

storage temp.

2-8°C

SMILES string

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

InChI key

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

Caution

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

Analysis Note

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

Other Notes

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

replaced by

Product No.
Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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