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
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
SMILES string
Cl.Cl.COC(=N)CCSSCCC(=N)OC
InChI key
CQBCVFHLZAVNPF-UHFFFAOYSA-N
form
powder
reaction suitability
reagent type: cross-linking reagent
solubility
H2O: 50 mg/mL
storage temp.
2-8°C
Quality Level
Related Categories
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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John G Lock et al.
Nature cell biology, 20(11), 1290-1302 (2018-10-27)
Adhesion to the extracellular matrix persists during mitosis in most cell types. However, while classical adhesion complexes, such as focal adhesions, do and must disassemble to enable mitotic rounding, the mechanisms of residual mitotic cell-extracellular matrix adhesion remain undefined. Here
Carine F Djuika et al.
Scientific reports, 7(1), 4410-4410 (2017-07-02)
Artemisinins are the current mainstay of malaria chemotherapy. Their exact mode of action is an ongoing matter of debate, and several factors have recently been reported to affect an early stage of artemisinin resistance of the most important human malaria
Lalit Yadav et al.
Organic & biomolecular chemistry, 18(30), 5927-5936 (2020-07-22)
A Bu4NI-catalyzed, DTBP-promoted, regioselective C(sp2)-C(sp3) cross dehydrogenative coupling (CDC) protocol for the direct C-3 benzylation of 2H-indazoles is reported. The metal-free protocol is operationally simple and proceeds mechanistically via the generation of stable benzylic free-radicals followed by regioselective addition at
Hyun Su Min et al.
Biomacromolecules, 19(6), 2320-2329 (2018-05-17)
Antibody fragment (Fab')-installed polyion complex (PIC) micelles were constructed to improve targetability of small interfering RNA (siRNA) delivery to pancreatic cancer cells. To this end, we synthesized a block copolymer of azide-functionalized poly(ethylene glycol) and poly(l-lysine) and prepared PIC micelles
K Satoh et al.
Biochemistry, 40(2), 314-319 (2001-01-10)
We investigated whether the assembly/disassembly of the 26S proteasome is regulated by phosphorylation/dephosphorylation. The regulatory complex disassembled from the 26S proteasome was capable of phosphorylating the p45/Sug1/Rpt6 subunit, suggesting that the protein kinase is activated upon dissociation of the 26S
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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