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Merck
CN

03450

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

purum, ≥98.0% (AT)

Synonym(s):

N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC, EDC hydrochloride, WSC hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C8H17N3 · HCl
CAS Number:
Molecular Weight:
191.70
UNSPSC Code:
12352111
NACRES:
NA.31
PubChem Substance ID:
EC Number:
247-361-2
Beilstein/REAXYS Number:
5764110
MDL number:
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grade

purum

Quality Level

assay

≥98.0% (AT)

form

powder

mp

110-115 °C

solubility

H2O: soluble 1 gm/10 ml, clear to very slightly hazy, colorless to very faintly yellow

application(s)

microbiology

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

General description

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDAC HCl), commonly known as EDAC, is a crucial water-soluble reagent widely employed in chemical and biochemical research, particularly for its proficiency in mediating amide bond formation. Notably effective in peptide synthesis, EDAC HCl demonstrates efficiency in coupling amino acids through their carboxyl and amine groups, enabling the tailored creation of peptides with specific sequences and functionalities. Extending its utility, EDAC HCl plays a pivotal role in the construction of immunogens by covalently attaching haptens—small immune-response eliciting molecules—to carrier proteins, a critical aspect in vaccine research.

The adaptability of EDAC HCl encompasses nucleic acid modification, permitting the selective labeling of DNA and RNA through their 5′ phosphate groups. This capacity contributes significantly to the visualization, tracking, and analytical aspects of these fundamental molecules, thereby advancing nucleic acid research. Furthermore, EDAC HCl functions as a biomolecule bridge, acting as a crosslinker connecting amine-reactive NHS-esters of biomolecules to carboxyl groups.

This feature proves invaluable in protein conjugation, facilitating the development of hybrid molecules with distinct properties and functions. The underlying reaction mechanism involves EDAC HCl′s interaction with a carboxyl group, forming an unstable intermediate actively seeking an amine partner. The delicate equilibrium of this reaction underscores the necessity for optimizing conditions to ensure efficient conjugation. The assistance of N-hydroxysuccinimide (NHS) enhances the capabilities of EDAC HCl by stabilizing the intermediate and enabling two-step conjugation procedures, affording greater flexibility and control, particularly in the manipulation of complex biomolecular structures.

Application

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used modify the cell surface of Escherichia coli to covalently couple substances. It has also been used as an activator to modify microfluidic chips to capture Escherichia coli.

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. Additionally, it reacts with phosphate groups. It has been utilized in peptide synthesis, crosslinking proteins to nucleic acids as well as preparation of immunoconjugates.
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 a wide variety of laboratory and research applications

Other Notes

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signalword

Danger

target_organs

Stomach,large intestine,lymph node

Storage Class

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

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



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Understanding bacterial uptake by protozoa: A versatile technique for surface modification of bacteria
Siegmund L and Wostemeyer J
Endocytobiosis and cell research, 27, 17-21 (2016)
Ahu Arslan Yildiz et al.
Analytical biochemistry, 423(1), 39-45 (2012-02-07)
The analysis of membrane proteins is notoriously difficult because isolation and detergent-mediated reconstitution often results in compromising the protein structure and function. We introduce a novel strategy of combining a cell-free expression method for synthesis of a protein species coping
Heather M Powell et al.
Biomaterials, 27(34), 5821-5827 (2006-08-22)
Collagen-based scaffolds are extensively utilized as an analog for the extracellular matrix in cultured skin substitutes (CSS). To improve the mechanical properties and degradation rates of collagen scaffolds, chemical cross-linking is commonly employed. In this study, freeze-dried collagen-GAG sponges were



Global Trade Item Number

SKUGTIN
101722005004022536024080
652458-100G04061832732671
652458-25G04061832732688
236101-500G04061838785466
202746-20G04061838765222
03450-5G04061835540891
03450-1G04061838618788
03450-25G04061835540884