E6383

N-(3-dimetilaminopropilo)-N′-etilcarbodiimida hydrochloride

crystalline

• Sinónimos: N-etil-N′-(3-dimetilaminopropil)carbodiimida hydrochloride, EDAC, EDC, EDC hydrochloride, WSC hydrochloride
• Fórmula empírica (notación de Hill): C₈H₁₇N₃ · HCl
• Número de CAS: 25952-53-8
• Peso molecular: 191.70
• Beilstein: 5764110
• Número CE: 247-361-2
• Número MDL: MFCD00012503
• Código UNSPSC: 12161703
• ID de la sustancia en PubChem: 24894627
• NACRES: NA.28

Propiedades

• Nombre del producto: N-(3-dimetilaminopropilo)-N′-etilcarbodiimida hydrochloride, crystalline
• Formulario: crystalline
• Nivel de calidad: 200
• idoneidad de la reacción: reagent type: cross-linking reagent; reaction type: Peptide Synthesis
• color: white to off-white
• mp: 110-115 °C (lit.)
• solubilidad: H₂O: ≤100 mg/mL
• aplicaciones: advanced drug delivery; general analytical
• temp. de almacenamiento: −20°C
• cadena SMILES: Cl.CCN=C=NCCCN(C)C
• InChI: 1S/C8H17N3.ClH/c1-4-9-8-10-6-5-7-11(2)3;/h4-7H2,1-3H3;1H
• Clave InChI: FPQQSJJWHUJYPU-UHFFFAOYSA-N

Descripción

Descripción general

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, commonly known as EDAC HCl, is a potent and widely employed water-soluble reagent in chemical and biochemical research due to its pivotal role in facilitating amide bond formation. In peptide synthesis, EDC HCl demonstrates efficiency by coupling amino acids through their carboxyl and amine groups, thereby forming peptide backbones. This capability is particularly valuable for creating peptides with specific sequences and functionalities.

Beyond peptides, EDC HCl extends its influence to the construction of immunogens, where it covalently attaches haptens (small immune-response eliciting molecules) to carrier proteins, playing an instrumental role in vaccine research. The versatility of EDAC HCl further unfolds in its ability to modify nucleic acids, allowing for the labeling of DNA and RNA through their 5′ phosphate groups. This facilitates the visualization, tracking, and analysis of these essential molecules, contributing to advancements in nucleic acid research.

Additionally, EDAC HCl serves as a biomolecule bridge by acting as a crosslinker, connecting amine-reactive NHS-esters of biomolecules to carboxyl groups. This technique proves valuable in protein conjugation, enabling the creation of hybrid molecules with novel properties and functions. The underlying mechanism of EDAC HCl involves its reaction with a carboxyl group, forming an unstable intermediate that actively seeks an amine partner. The delicate balance of this reaction underscores the importance of optimizing conditions for efficient conjugation. The assistance of N-hydroxysuccinimide (NHS) further enhances EDAC HCl′s capabilities, stabilizing the intermediate and enabling two-step conjugation procedures. This additional feature provides greater flexibility and control, particularly in dealing with complex biomolecules.

Aplicación

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used:

• for the immobilisation of trypsin onto self-assembled monolayers (SAMs)
• as a component for the preparation of collagen matrices
• for the preparation of phosphoethanolamine(PEt)-conjugated sepharose

Acciones bioquímicas o fisiológicas

Reactivo de condensación hidrosoluble. El EDAC se utiliza generalmente como activador de carboxilos para la formación del enlace amida con las aminas primarias. Además, reaccionará con los grupos de fosfato. El EDAC se ha utilizado en la síntesis de péptidos; la formación de enlaces transversales entre proteínas y ácidos nucleicos; y la preparación de inmunoconjugados como ejemplos. Normalmente, el EDAC se utiliza en el intervalo de pH 4,0-6,0 sin disoluciones tampón. En particular, deben evitarse los tampones de amina y carboxilato.

Características y beneficios

Versatile and adaptable for a wide variety of laboratory and research applications

Otras notas

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Información de seguridad

• Pictogramas: GHS06,GHS08,GHS09
• Palabra de señalización: Danger
• Frases de peligro: H302,H311,H315,H317,H373,H410
• Consejos de prudencia: P260 - P273 - P280 - P301 + P312 - P302 + P352 + P312 - P314
• Clasificaciones de peligro: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Oral
• Órganos de actuación: Stomach,large intestine,lymph node
• Código de clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: dust mask type N95 (US), Eyeshields, Gloves