E6383
N-(3-Diméthylaminopropyl)-N′-éthylcarbodiimide hydrochloride
crystalline
Synonyme(s) :
N-Éthyl-N′-(3-diméthylaminopropyl) carbodiimide hydrochloride, EDAC, EDC, EDC hydrochloride, WSC hydrochloride
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About This Item
Formule empirique (notation de Hill):
C8H17N3 · HCl
Numéro CAS:
Poids moléculaire :
191.70
Numéro Beilstein :
5764110
Numéro CE :
Numéro MDL:
Code UNSPSC :
12161703
ID de substance PubChem :
Nomenclature NACRES :
NA.28
Produits recommandés
product name
N-(3-Diméthylaminopropyl)-N′-éthylcarbodiimide hydrochloride, crystalline
Forme
crystalline
Niveau de qualité
Pertinence de la réaction
reagent type: cross-linking reagent
reaction type: Peptide Synthesis
Couleur
white to off-white
Pf
110-115 °C (lit.)
Solubilité
H2O: ≤100 mg/mL
Application(s)
advanced drug delivery
general analytical
Température de stockage
−20°C
Chaîne 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
Clé InChI
FPQQSJJWHUJYPU-UHFFFAOYSA-N
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Description générale
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.
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.
Application
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
Actions biochimiques/physiologiques
Réactif de condensation soluble dans l′eau. L′EDAC est généralement utilisé comme agent d′activation du carboxyle pour la formation de liaisons amide avec des amines primaires. En outre, il réagit avec les groupes phosphate. L′EDAC a été utilisé dans la synthèse peptidique, la réticulation de protéines aux acides nucléiques et la préparation d′immunoconjugués, à titre d′exemple. L′EDAC est généralement utilisé dans une gamme de pH comprise entre 4,0 et 6,0, sans tampons. En particulier, les tampons amines et carboxylates doivent être évités.
Caractéristiques et avantages
Versatile and adaptable for a wide variety of laboratory and research applications
Autres remarques
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Réf. du produit
Description
Tarif
Mention d'avertissement
Danger
Mentions de danger
Conseils de prudence
Classification des risques
Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Oral
Organes cibles
Stomach,large intestine,lymph node
Code de la classe de stockage
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Équipement de protection individuelle
dust mask type N95 (US), Eyeshields, Gloves
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