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Carbodiimides
Carbodiimides
Carbodiimides are a class of organic compounds with the general formula R-N=C=N-R', where R and R' are organic substituents.
They are widely used as coupling agents in chemical synthesis, particularly in the formation of amide bonds between carboxylic acids and amines.
Carbodiimides promote the formation of stable peptide and ester linkages, making them indispensable tools in fields such as organic chemistry, biochemistry, and materials science.
Their ability to activate carboxyl groups and facilitate condensation reactions has led to their widespread application in the synthesis of pharmaceuticals, polymers, and biomolecules.
Researchers utilzing carbodiimides must carefully optimize reaction condiitons to ensure high yields and reproducibility.
They are widely used as coupling agents in chemical synthesis, particularly in the formation of amide bonds between carboxylic acids and amines.
Carbodiimides promote the formation of stable peptide and ester linkages, making them indispensable tools in fields such as organic chemistry, biochemistry, and materials science.
Their ability to activate carboxyl groups and facilitate condensation reactions has led to their widespread application in the synthesis of pharmaceuticals, polymers, and biomolecules.
Researchers utilzing carbodiimides must carefully optimize reaction condiitons to ensure high yields and reproducibility.
Most cited protocols related to «Carbodiimides»
Acquired Immunodeficiency Syndrome
Antigens
Biological Assay
Carbodiimides
Cardiac Arrest
Centrifugation
GP 140
HIV Antigens
HIV Envelope Protein gp120
Microspheres
Polystyrenes
Sodium Azide
sodium phosphate, monobasic
Tween 20
Optical fiber bundles were purchased from Schott North America (Southbridge, MA). Non-reinforced gloss silicone sheeting was obtained from Specialty Manufacturing (Saginaw, MI). Hydrochloric acid, anhydrous ethanol, and molecular biology grade Tween-20 were all from Sigma-Aldrich (Saint Louis, MO). 2.7-μm-diam. carboxyl-terminated magnetic beads were purchased from Varian, Inc. (Lake Forest, CA). Monoclonal anti-human TNF-α capture antibody, polyclonal anti-human TNF-α detection antibody, and recombinant human TNF-α were purchased from R&D Systems (Minneapolis, MN). Monoclonal anti-PSA capture antibody, monoclonal anti-PSA detection antibody, and purified PSA were purchased from BiosPacific (Emeryville, CA); the detection antibody was biotinylated using standard methods. 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), N-hydroxysulfosuccinimide (NHS), and SuperBlock® T-20 Blocking Buffer were purchased from Thermo Scientific (Rockford, IL). Purified DNA was purchased from Integrated DNA Technologies (Coralville, IA). Streptavidin-β-galactosidase (SβG) was conjugated in house using standard protocols. Resorufin-β-D-galactopyranoside (RGP) was purchased from Invitrogen (Carlsbad, CA). The fiber polisher and polishing consumables were purchased from Allied High Tech Products (Rancho Dominguez, CA).
Absolute Alcohol
Antibodies, Anti-Idiotypic
Buffers
Carbodiimides
Etanercept
Fibrosis
Forests
GLB1 protein, human
Homo sapiens
Hydrochloric acid
Immunoglobulins
Monoclonal Antibodies
N-hydroxysulfosuccinimide
resorufin galactopyranoside
Silicones
Streptavidin
TNF protein, human
Tween 20
Acetic Acids
Aluminum
Anisotropy
ARID1A protein, human
Bos taurus
Carbodiimides
Collagen Type I
Copper
Dermis
Ethanol
Freeze Drying
Fungus, Filamentous
Molar
N-hydroxysulfosuccinimide
Phosphates
Polytetrafluoroethylene
Saline Solution
shark cartilage extract
Sulfates, Chondroitin
Vacuum
Amines
anti-IgG
Antibodies
ARID1A protein, human
Biological Assay
Buffers
Carbodiimides
COVID 19
Fluorescence
HEK293 Cells
Homo sapiens
Immunoglobulin Fc Fragments
Patients
Proteins
SARS-CoV-2
Serum
Sodium Azide
Technique, Dilution
Tween 20
Tweens
Vacuum
HIV antigens were conjugated to magnetic carboxylated fluorescent beads (Luminex Corporation) as described previously (Brown et al., 2012 (link)) with minor changes. Antigens tested included proteins, peptides, and even whole inactivated virus, as described previously for poliovirus (Wright et al., 2014 (link)). Antigens highlighted in this work were mostly obtained from Immune Technologies (HIV and some SIV envelopes) or the NIH AIDS Reagent Program (HIV non-envelope proteins, some SIV envelopes). Briefly, a total of 5 million carboxylated beads (400 μL) were coupled to 25 μg of antigen using a two-step carbodiimide reaction using magnetic separation, a procedure which can be scaled down based on a ratio of 5 μg antigen per million beads. Bead storage buffer was removed via magnetic separation and the beads were washed with 100 μL of dH2O prior to activation for 20 min by suspension in 80 μL of Activation Buffer (100 mM monobasic sodium phosphate, pH 6.2), followed by the addition of 10 μL each of 50 mg/mL N-hydroxysulfosuccinimide (Sulfo-NHS, Pierce #24520) and 1-ethyl-3-[3-dimethlyaminopropyl]carbodiimide-HCl (EDC, Pierce #77149) dissolved in Activation Buffer. Activated beads were washed three times in 250 μL of Coupling Buffer (50 mM MES, pH 5.0), resuspended in 100 μL of Coupling Buffer, and incubated with 25 μg of antigen for 2 h on a rotational mixer. Finally, coupled beads were washed three times with 200 μL of PBS-TBN (PBS-1X, 0.1% BSA, 0.02% Tween 20, 0.05% Sodium Azide, pH 7.4) and blocked in 250 μL of PBS-TBN. After either 30 min (room temperature) or overnight (4 °C) incubation in PBS-TBN, beads were washed to remove blocking buffer and resuspended in PBS-TBN for storage. The coupled beads were counted and stored at − 80 °C for up to 6 months or at 4 °C for up to 1 month prior to use.
Minor modifications to this procedure have been made for evaluation of biotinylated proteins and peptides, and for evaluation of glycoprotein antigens with lectin detection reagents. Briefly, for biotinylated antigens, streptavidin was conjugated directly to the beads as described above, followed by a 30 min incubation with 5 μg of biotinylated antigen per million beads and three subsequent washes with 200 μL of PBS-TBN. For assessment with lectin detection reagents, antigen-conjugated beads were pretreated with PNGaseF enzyme. Conjugated beads were buffer exchanged into 20 mM Tris pH 8.2 in a 1.5 mL Eppendorf tube to a final concentration of 100 beads per type per μL. PNGase F enzyme (NEB P0704S, 500 units/μL) was then added to a final concentration of 2000 (low) or 10,000 (high) units of enzyme per million beads. The beads were incubated overnight at 37 °C with rotation, after which they were buffer exchanged into Assay Buffer prior to use.
Minor modifications to this procedure have been made for evaluation of biotinylated proteins and peptides, and for evaluation of glycoprotein antigens with lectin detection reagents. Briefly, for biotinylated antigens, streptavidin was conjugated directly to the beads as described above, followed by a 30 min incubation with 5 μg of biotinylated antigen per million beads and three subsequent washes with 200 μL of PBS-TBN. For assessment with lectin detection reagents, antigen-conjugated beads were pretreated with PNGaseF enzyme. Conjugated beads were buffer exchanged into 20 mM Tris pH 8.2 in a 1.5 mL Eppendorf tube to a final concentration of 100 beads per type per μL. PNGase F enzyme (NEB P0704S, 500 units/μL) was then added to a final concentration of 2000 (low) or 10,000 (high) units of enzyme per million beads. The beads were incubated overnight at 37 °C with rotation, after which they were buffer exchanged into Assay Buffer prior to use.
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Acquired Immunodeficiency Syndrome
Antigens
Biological Assay
Carbodiimides
Cardiac Arrest
Enterovirus C, Human
Enzymes
Glycopeptidase F
Glycoproteins
HIV Antigens
Human Immunodeficiency Virus Proteins
Lectin
N-hydroxysulfosuccimide
Peptides
Proteins
Sodium Azide
sodium phosphate, monobasic
Streptavidin
Tromethamine
Tween 20
Virus
Most recents protocols related to «Carbodiimides»
Example 7
A reaction vessel equipped with a reflux condenser and a stirrer was charged with a diisocyanate compound, an end-capping agent, a solvent (THF), and a carbodiimidization catalyst shown in Table 1 at a ratio shown in Table 1, and the mixture was stirred under a nitrogen flow at 70° C. for 3 hours.
Then, it was confirmed by IR spectrum measurement that an absorption peak attributed to an isocyanate group at a wavelength of about 2270 cm−1 almost disappeared, and a THF solution of a carbodiimide compound of n=6 was obtained. Then, the THF was volatilized, followed by drying, to obtain a carbodiimide compound P7.
Example 8
In synthetic Example 8, a carbodiimide compound P8 of n=6 was obtained in the same manner as in Synthetic Example 7 except that a diisocyanate compound, an end-capping agent, a solvent, and a carbodiimidization catalyst shown in Table 1 were blended at a ratio shown in Table 1.
Example 9
In synthetic Example 9, a carbodiimide compound P9 of n=6 was obtained in the same manner as in Synthetic Example 7 except that a diisocyanate compound, an end-capping agent, a solvent, and a carbodiimidization catalyst shown in Table 1 were blended at a ratio shown in Table 1.
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Blood Vessel
Carbodiimides
fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether
Isocyanates
Nitrogen
Polyesters
Resins, Plant
Solvents
Example 10
A reaction vessel equipped with a reflux condenser and a stirrer was charged with a diisocyanate compound and a carbodiimidization catalyst shown in Table 1 at a ratio shown in Table 1, and the mixture was stirred under a nitrogen flow at 185° C. for 24 hours to obtain isocyanate-terminated poly-4,4′-dicyclohexylmethane carbodiimide.
The measured ratio of NCO was 3.78%, and n was 9.
Then, the isocyanate-terminated poly-4,4′-dicyclohexylmethane carbodiimide was heated to 150° C., and 14.2 parts by mass of an end-capping agent shown in Table 1 was added thereto, followed by stirring for 3 hours. Then, it was confirmed by IR spectrum measurement that an absorption peak attributed to an isocyanate group at a wavelength of about 2270 cm−1 almost disappeared, and a carbodiimide compound P10 of n=9 was obtained.
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Blood Vessel
Carbodiimides
dicyclohexylmethane
fluoromethyl 2,2-difluoro-1-(trifluoromethyl)vinyl ether
Isocyanates
Nitrogen
Poly A
Polyesters
Resins, Plant
Example 7
t-TUCB (245 mg, 0.56 mmol), benzyl alcohol (200 uL, 1.93 mmol), 1-ethyl-3-dimethylaminopropyl)carbodiimide (EDCI, 148 mg, 0.95 mmol), 4-dimethylaminopyridine (DMAP, 5 mg, 0.04 mmol) and trimethylamine (Et3N, 63 mg, 0.62 mmol) were dissolved in THF and stirred overnight. The product was extracted twice with a saturated solution of NaHCO3 and once with 1 M HCl. The product was dried over MgSO4, evaporated and purified by flash chromatography with 100% EtOAc. The final product was recrystallized in EtOAc (34 mg, 0.06 mmol, 11%). MP=186.9-189.6° C. (188.1° C.) 1H NMR (400 MHz, DMSO-d6) δ 8.47 (s, 1H), 7.87 (d, J=8.9 Hz, 2H), 7.47-7.26 (m, 6H), 7.16 (d, J=8.8 Hz, 2H), 7.02 (d, J=8.9 Hz, 1H), 6.15 (d, J=7.9 Hz, 1H), 5.26 (s, 2H), 4.41 (s, 1H), 3.47 (s, 1H), 1.99 (s, 2H), 1.88 (s, 2H), 1.45 (q, J=11.1, 10.3 Hz, 2H), 1.32 (q, J=11.2 Hz, 2H).
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1H NMR
4-dimethylaminopyridine
Benzoate
Benzyl Alcohol
Bicarbonate, Sodium
Carbodiimides
Chromatography
Sulfate, Magnesium
Sulfoxide, Dimethyl
t-TUCB
trimethylamine
Example 148
To a stirred solution of (R)-2-oxo-3-phenyloxazolidine-5-carboxylic acid (100 mg, 482.67 μmol) in dichloromethane (2 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (111 mg, 579 μmol), HOBt (78 mg, 579 μmol), triethylamine (146 mg, 1.45 mmol, 200 μL) and 3-(4-ethoxy-3-methoxyphenyl)-5-(piperidin-4-yl)-1,2,4-oxadiazole hydrochloride (164 mg, 482.67 μmol). The reaction mixture was stirred at 25° C. for 12 h and then concentrated under reduced pressure. The residue was purified by prep-HPLC (column: Boston Green ODS 150×30 5 μm; mobile phase: [water (10 mM ammonium carbonate)-acetonitrile]; B%: 45%-75%, 11.5 min) to give (R)-5-(4-(3-(4-ethoxy-3-methoxyphenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carbonyl)-3-phenyloxazolidin-2-one (139 mg, 280 μmol, 58%) as a pale yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.67 (d, J=8.3 Hz, 1H), 7.59-7.55 (m, 3H), 7.40 (t, J=7.7 Hz, 2H), 7.17 (t, J=6.9 Hz, 1H), 6.95 (dd, J=1.1, 8.6 Hz, 1H), 5.25 (ddd, J=3.1, 6.2, 9.1 Hz, 1H), 4.81 (dd, J=6.8, 8.6 Hz, 1H), 4.58 (br d, J=14.0 Hz, 0.5H), 4.37-4.21 (m, 1H), 4.17 (q, J=7.0 Hz, 2H), 4.07 (dt, J=2.6, 9.0 Hz, 1.5H), 3.96 (d, J=2.2 Hz, 3H), 3.59 (ddd, J=3.3, 10.3, 14.0 Hz, 0.5H), 3.41-3.17 (m, 2H), 3.09-3.00 (m, 0.5H), 2.34-1.95 (m, 4H), 1.54-1.47 (m, 3H); LCMS (ESI) m/z: [M+H]+=493.3.
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1-hydroxybenzotriazole
1H NMR
acetonitrile
ammonium carbonate
Carbodiimides
Carboxylic Acids
Chloroform
Green S
High-Performance Liquid Chromatographies
Lincomycin
Methylene Chloride
Oxadiazoles
piperidine
Pressure
triethylamine
Glycol chitosan (Mw = 250 kDa, 5β-cholanic acid, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) were purchased from Sigma Aldrich (St. Louis, MO, USA). Flamma 648 NHS ester was purchased from BioActs (Incheon, Republic of Korea). Cell counting kit-8 (CCK-8) was purchased from Vitascientific (Beltsville, MD, USA). Tem grid (Carbon Film 200 Mesh copper) was purchased from Electron Microscopy Sciences (Hatfield, PA, USA). H9C2 (Rat cardiomyocyte), L929 (mouse fibroblast) and Raw264.7 (macrophage) cell lines were purchased from American Type Culture Collection (ATCC; Manassas, VA, USA). Fetal bovine serum (FBS), streptomycin, penicillin and RPMI 1640 medium were purchased from WELGENE Inc. (Daegu, Republic of Korea). Antibodies against mouse TNF-α (cat# 109,828), mouse IL1b, mouse IL6 and mouse β-actin were purchased from BioLegend (San Diego, CA, USA).
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Actins
Antibodies
Carbodiimides
Carbon
Cell Lines
cholanic acid
Copper
Electron Microscopy
Esters
Fetal Bovine Serum
Fibroblasts
glycol-chitosan
Interleukin-1
Macrophage
Mus
Myocytes, Cardiac
N-hydroxysuccinimide
Penicillins
Streptomycin
Tumor Necrosis Factor-alpha
Top products related to «Carbodiimides»
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N-hydroxysuccinimide is a chemical compound commonly used as an activating agent in organic synthesis. It is a stable, crystalline solid that can be used to facilitate the formation of amide bonds between carboxylic acids and primary amines. Its core function is to activate carboxylic acids, enabling their subsequent reaction with other functional groups.
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N-hydroxysuccinimide (NHS) is a chemical compound used in various laboratory applications. It serves as an activating agent, primarily in the field of organic synthesis and biomolecular conjugation.
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1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) is a water-soluble carbodiimide compound commonly used as a coupling agent in chemical reactions. Its core function is to facilitate the formation of amide bonds between carboxyl and amine groups in various biomolecules, such as proteins, peptides, and nucleic acids.
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Bovine serum albumin (BSA) is a common laboratory reagent derived from bovine blood plasma. It is a protein that serves as a stabilizer and blocking agent in various biochemical and immunological applications. BSA is widely used to maintain the activity and solubility of enzymes, proteins, and other biomolecules in experimental settings.
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1-ethyl-3-(3-dimethylaminopropyl) carbodiimide is a lab equipment chemical compound used for protein coupling reactions. It is a water-soluble carbodiimide that can be used to activate carboxyl groups for conjugation with primary amines.
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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) is a chemical compound commonly used in various laboratory applications. It is a water-soluble carbodiimide that facilitates the formation of amide bonds between carboxyl groups and primary amines. EDC is a versatile reagent that can be used in a wide range of chemical reactions and biological applications.
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Sodium hydroxide is a chemical compound with the formula NaOH. It is a white, odorless, crystalline solid that is highly soluble in water and is a strong base. It is commonly used in various laboratory applications as a reagent.
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1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) is a chemical compound commonly used as a coupling agent in various laboratory applications. Its core function is to facilitate the formation of amide bonds between carboxyl groups and primary amines. EDC is widely utilized in biomolecular and organic synthesis processes, particularly in the fields of protein conjugation, peptide synthesis, and the preparation of bioconjugates.
More about "Carbodiimides"
Carbodiimides are a versatile class of organic compounds that play a crucial role in chemical synthesis, particularly in the formation of amide bonds between carboxylic acids and amines.
These compounds, with the general formula R-N=C=N-R', where R and R' are organic substituents, are widely used as coupling agents.
Their ability to activate carboxyl groups and facilitate condensation reactions has made them indispensable tools in various fields, such as organic chemistry, biochemistry, and materials science.
One of the key applications of carbodiimides is in the synthesis of pharmaceuticals, polymers, and biomolecules.
These compounds promote the formation of stable peptide and ester linkages, making them essential for researchers working in these domains.
Closely related to carbodiimides are N-hydroxysuccinimide (NHS) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), which are often used in conjunction with carbodiimides to enhance the efficiency and specificity of coupling reactions.
In the context of biochemical research, carbodiimides are frequently employed in the immobilization of proteins, such as Bovine serum albumin (BSA) and fetal bovine serum (FBS), onto various surfaces.
This technique is widely used in the development of biosensors, immunoassays, and affinity chromatography applications.
Additionally, carbodiimides find use in the modification of biomolecules, including the conjugation of proteins, peptides, and small molecules, which is crucial for the creation of drug-delivery systems and the study of biological processes.
To optimize the use of carbodiimides in research, it is important to carefully consider the reaction conditions, such as pH, temperature, and the presence of other reagents like DMSO and sodium hydroxide.
Researchers can utilize platforms like PubCompare.ai to compare protocols from literature, pre-prints, and patents, and identify the most reproducible and accurate methodologies.
This can help streamline the research process and enhance the reproducibility of experiments involving carbodiimides.
By understanding the versatility and applications of carbodiimides, researchers can leverage these powerful coupling agents to advance their work in the fields of organic chemistry, biochemistry, and materials science.
With the right tools and optimization strategies, the use of carbodiimides can be a key factor in driving innovative discoveries and developments.
These compounds, with the general formula R-N=C=N-R', where R and R' are organic substituents, are widely used as coupling agents.
Their ability to activate carboxyl groups and facilitate condensation reactions has made them indispensable tools in various fields, such as organic chemistry, biochemistry, and materials science.
One of the key applications of carbodiimides is in the synthesis of pharmaceuticals, polymers, and biomolecules.
These compounds promote the formation of stable peptide and ester linkages, making them essential for researchers working in these domains.
Closely related to carbodiimides are N-hydroxysuccinimide (NHS) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), which are often used in conjunction with carbodiimides to enhance the efficiency and specificity of coupling reactions.
In the context of biochemical research, carbodiimides are frequently employed in the immobilization of proteins, such as Bovine serum albumin (BSA) and fetal bovine serum (FBS), onto various surfaces.
This technique is widely used in the development of biosensors, immunoassays, and affinity chromatography applications.
Additionally, carbodiimides find use in the modification of biomolecules, including the conjugation of proteins, peptides, and small molecules, which is crucial for the creation of drug-delivery systems and the study of biological processes.
To optimize the use of carbodiimides in research, it is important to carefully consider the reaction conditions, such as pH, temperature, and the presence of other reagents like DMSO and sodium hydroxide.
Researchers can utilize platforms like PubCompare.ai to compare protocols from literature, pre-prints, and patents, and identify the most reproducible and accurate methodologies.
This can help streamline the research process and enhance the reproducibility of experiments involving carbodiimides.
By understanding the versatility and applications of carbodiimides, researchers can leverage these powerful coupling agents to advance their work in the fields of organic chemistry, biochemistry, and materials science.
With the right tools and optimization strategies, the use of carbodiimides can be a key factor in driving innovative discoveries and developments.