D2388
Dimethyl 3,3′-dithiopropionimidate dihydrochloride
powder
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:
Molecular Weight:
309.28
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352116
MDL number:
Form:
powder
form
powder
reaction suitability
reagent type: cross-linking reagent
solubility
H2O: 50 mg/mL
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
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
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.
Disclaimer
The reagant is readily hydrolyzed at neutral pH. Avoid use of reducing agents during coupling reactions.
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Articles
Kanjiro Miyata (The University of Tokyo, Japan) provides insights on the rational design of polymeric materials for “smart” oligonucleotide delivery.
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| D2388-100MG | 04061833284629 |