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N,N,N, -tris(3-dimethylaminopropyl-) amine is a water-soluble carbodiimide available as hydrochloride salt.
N,N,N, -tris(3-dimethylaminopropyl-) amine is a carboxyl- and amine-reactive crosslinker that is water soluble and can activate carboxyl residues for their reaction with primary amines to form O-acylisourea as a reaction intermediate, which reacts with amide bonds to release isourea as a by-product.
N,N,N, -tris(3-dimethylaminopropyl-) amine can crosslink the carboxy-group of glutamate and aspartate to the side-chain primary amine of lysine and the amino group at the N-terminus.
CAS: 1892-57-5
MF: C8H17N3
MW: 155.24
EINECS: 217-579-2
Synonyms
1-ETHYL-3-(3-DIMETHYLAMINOPROPYL) CARBODIIMIDE;1-(3-DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE;WATER-SOLUBLE CARBODIIMIDE;WSCD;WSCI;N-ETHYL-N'-(3-DIMETHYLAMINOPROPYL)CARBODIIMIDE;[3-(Dimethylamino)propyl]ethylcarbodiimide;ethyldimethylaminopropylcarbodiimide
The crosslinker readily reacts at a pH range of 4.5–7.2 and only crosslinks the residues within their van der Waals distance.
N,N,N, -tris(3-dimethylaminopropyl-) amine is also widely used in fabricating different nanosystems implemented in drug/protein delivery systems.
N,N,N, -tris(3-dimethylaminopropyl-) amine is mainly used for surface crosslinking/immobilization of drugs to increase stability against environmental changes, such as pH or temperature.
N,N,N, -tris(3-dimethylaminopropyl-) amine is commonly used in combination with N-hydroxysuccinimide (NHS) in carbodiimide coupling reaction to activate carboxyl group for coupling with amines to form amides.
N,N,N, -tris(3-dimethylaminopropyl-) amine is a water-soluble carbodiimide usually handled as the hydrochloride, which is a white solid.
N,N,N, -tris(3-dimethylaminopropyl-) amine is typically employed in the 4.0-6.0 pH range.
N,N,N, -tris(3-dimethylaminopropyl-) amine is generally used as a carboxyl activating agent for the coupling of primary amines to yield amide bonds.
While other carbodiimides like dicyclohexylcarbodiimide (DCC) or diisopropylcarbodiimide (DIC) are also employed for this purpose, EDC has the advantage that the urea byproduct formed (often challenging to remove in the case of DCC or DIC) can be washed away from the amide product using dilute acid.
Additionally, N,N,N, -tris(3-dimethylaminopropyl-) amine can also be used to activate phosphate groups in order to form phosphomonoesters and phosphodiesters.
Common uses for this carbodiimide include peptide synthesis, protein crosslinking to nucleic acids, but also in the preparation of immunoconjugates.
N,N,N, -tris(3-dimethylaminopropyl-) amine is often used in combination with N-hydroxysuccinimide (NHS) for the immobilisation of large biomolecules.
Recent work has also used N,N,N, -tris(3-dimethylaminopropyl-) amine to assess the structure state of uracil nucleobases in RNA.
N,N,N, -tris(3-dimethylaminopropyl-) amine, commonly referred to as EDC, is a water-soluble carbodiimide used primarily as a coupling agent in peptide synthesis and other organic reactions.
N,N,N, -tris(3-dimethylaminopropyl-) amine facilitates the formation of amide bonds between carboxylic acids and amines by activating the carboxyl group, making it more reactive towards nucleophilic attack.
N,N,N, -tris(3-dimethylaminopropyl-) amine is characterized by its ability to promote reactions in aqueous environments, which is advantageous for bioconjugation applications.
The compound typically appears as a colorless to pale yellow liquid and has a relatively low molecular weight.
N,N,N, -tris(3-dimethylaminopropyl-) amine's reactivity can be influenced by the presence of various functional groups in the reaction mixture.
N,N,N, -tris(3-dimethylaminopropyl-) amine is often used in conjunction with other reagents, such as N-hydroxysuccinimide (NHS), to enhance coupling efficiency and minimize side reactions.
Safety precautions are necessary when handling N,N,N, -tris(3-dimethylaminopropyl-) amine, as it can be irritating to the skin and eyes, and proper laboratory practices should be followed to mitigate exposure.
N,N,N, -tris(3-dimethylaminopropyl-) amine Chemical Properties
Boiling point: 66-68°C/1mm
Density: 0.877 g/mL at 20 °C (lit.)
Refractive index: n20/D 1.461
Fp: 66-68°C/1mm
Storage temp.: -20°C
Solubility: Chloroform
Pka: 9.52±0.28(Predicted)
Form: Liquid
Specific Gravity: 0.885
Color: Colorless to slightly yellow
Water Solubility: Soluble in water.
Sensitive: Air Sensitive
BRN: 507429
InChIKey: LMDZBCPBFSXMTL-UHFFFAOYSA-N
CAS DataBase Reference: 1892-57-5(CAS DataBase Reference)
NIST Chemistry Reference:N,N,N, -tris(3-dimethylaminopropyl-) amine(1892-57-5)
EPA Substance Registry System: N,N,N, -tris(3-dimethylaminopropyl-) amine(1892-57-5)
Uses
N,N,N, -tris(3-dimethylaminopropyl-) amine is used as a carboxyl activating agent and activate phosphate groups in phospho mono and di esters.
N,N,N, -tris(3-dimethylaminopropyl-) amine is used in peptide synthesis, 3'-amino-3'-deoxyadenosine-5'-di- and triphosphates and in the preparation of antibodies like immunoconjugates.
N,N,N, -tris(3-dimethylaminopropyl-) amine plays a vital role for immobilization of large biomolecules in association with N-hydroxysuccinimide.
N,N,N, -tris(3-dimethylaminopropyl-) amine is also used in the acylation of phosphoranes.
Synthesis
The production method of N,N,N, -tris(3-dimethylaminopropyl-) amine is to react with N, N'-dimethylpropanediamine and carbon disulfide as raw materials to prepare N, N'- Dimethylpropylthiourea.
Then N,N,N, -tris(3-dimethylaminopropyl-) amine is oxidized with ethyl chloroformate to obtain N, N'-dimethylpropyl isothiocyanate, which is then reacted with ethylamine and oxidized with sodium hypochlorite to obtain the product 1-(3-dimethylaminopropyl)-3- Ethylcarbodiimide.
