03449

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

≥99.0% (AT)

• Synonim(y): N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC, EDC hydrochloride, WSC hydrochloride
• Wzór empiryczny (zapis Hilla): C₈H₁₇N₃ · HCl
• Numer CAS: 25952-53-8
• Masa cząsteczkowa: 191.70
• NACRES: NA.21
• PubChem Substance ID: 329747707
• UNSPSC Code: 12161502
• EC Number: 247-361-2
• MDL number: MFCD00012503
• Beilstein/REAXYS Number: 5764110

Właściwości

• Quality Segment: 200
• assay: ≥99.0% (AT)
• form: powder
• technique(s): bioconjugation: suitable
• mp: 110-115 °C (lit.), 112-116 °C
• solubility: H₂O: soluble 0.2 g/L
• storage temp.: −20°C
• SMILES string: 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
• InChI key: FPQQSJJWHUJYPU-UHFFFAOYSA-N

Opis

General description

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, commonly referred to as EDAC HCl, plays a pivotal role as a potent and widely utilized water-soluble reagent in chemical and biochemical research, primarily facilitating the formation of amide bonds. In the realm of peptide synthesis, EDAC HCl showcases efficiency by coupling amino acids through their carboxyl and amine groups, crucial for the creation of peptides with specific sequences and functionalities. Expanding its influence beyond peptides, EDAC HCl contributes to the construction of immunogens by covalently attaching haptens—small molecules that elicit an immune response—to carrier proteins, playing a key role in vaccine research.The versatility of EDAC HCl extends to nucleic acid modification, allowing for the labeling of DNA and RNA through their 5′ phosphate groups. This capability facilitates the visualization, tracking, and analysis of these crucial molecules, contributing significantly to advancements in nucleic acid research.

Furthermore, EDAC HCl serves as a biomolecule bridge, acting as a crosslinker that connects amine-reactive NHS-esters of biomolecules to carboxyl groups. This technique proves invaluable in protein conjugation, enabling the creation of hybrid molecules with novel properties and functions. The underlying mechanism involves EDAC HCl′s 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 by stabilizing the intermediate and enabling two-step conjugation procedures. This additional feature provides greater flexibility and control, particularly when dealing with complex biomolecules.

Application

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride ≥99.0% (AT) has been used as an activator to covalently immobilize tyrosinase to prepare enzyme electrodes. It has also been used as a prefixative for histamine immunolabeling.

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used for amine coupling reaction during self-assembly of the tethered bilayer lipid membrane.[1] It has also been used for derivatizing antibody against COX5b to carboxylated polystyrene microspheres.[2]

Biochem/physiol Actions

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide is a water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines.[3] Additionally, it will react with phosphate groups. It has been utilized in peptide synthesis, crosslinking proteins to nucleic acids as well as preparation of immunoconjugates.[4]

Water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines. In addition, it will react with phosphate groups. EDAC has been used in peptide synthesis; crosslinking proteins to nucleic acids; and preparation of immunoconjugates as examples. Typically, EDAC is utilized in the pH range 4.0-6.0 without buffers. In particular, amine and carboxylate buffers should be avoided.

Features and Benefits

Versatile and adaptable for wide variety of laboratory and research applications

Other Notes

Water soluble peptide coupling reagent;[5] Modification of carboxyl groups in proteins, review; Synthesis of esters.

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Informacja o środkach bezpieczeństwa

• pictograms: GHS06,GHS08,GHS09
• signalword: Danger
• target_organs: Stomach,large intestine,lymph node
• Klasa składowania: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves
• hcodes: H302,H311,H315,H317,H319,H373,H410
• pcodes: P273 - P280 - P301 + P312 - P302 + P352 + P312 - P305 + P351 + P338 - P314
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Oral