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> Phenomena > Natural Phenomenon or Process > Amination

Amination

Amination is the process of introducing an amino group (-NH2) into a chemical compound.
This reaction is commonly used in organic synthesis to modify the structure and properties of molecules.
Amination can be achieved through various methods, such as nucleophilic addition, reductive amination, or direct amination.
The resulting aminated compounds find applications in pharmaceuticals, agrochemicals, dyes, and other specialized materials.
Researchers can optimize their amination protocols using AI-driven comparisons to locate the best procedures from literature, preprints, and patents, improving reproducibility and accuracy.
PubCompare.ai offers streamlined, data-driven research to help scientists overcome the challenges of manual protocol comparisons and enhance their amination studies.

Most cited protocols related to «Amination»

1
Quantitative Glycosaminoglycan Disaccharide Analysis
Enzymatically depolymerized GAG preparations were differentially mass labeled by reductive amination with [12C6]aniline as previously described13 (link). Briefly, HS and CS disaccharides (1–10 pmoles) were dried down in a centrifugal evaporator and reacted with [12C6]aniline or [13C6]aniline (15 µl, 165 µmol) and 15 µl of 1 M NaCNBH3 (Sigma-Aldrich) freshly prepared in dimethylsulfoxide:acetic acid (7:3, v/v) was added to each sample. Reactions were carried out at 65 °C for 4 h or alternatively at 37 °C for 16 h and then dried in a centrifugal evaporator. Unsubstituted amines were reacted with propionic anhydride (Sigma-Aldrich). Dried samples were reconstituted in 20 µl of 50% methanol and 3 µl of propionic anhydride (Sigma-Aldrich, 23.3 µmol) was added. Reactions were carried out at room temperature for 2 h. Acylated disaccharides were subsequently aniline-tagged as described above. Each sample was mixed with commercially available standard unsaturated disaccharides (Seikagaku), standard N-sulfoglucosamine, glucosamine-6-sulfate, N-acetylgalactosamine-4-sulfate and N-acetylgalactosamine-6-sulfate (Sigma-Aldrich), and/or β-d-idopyranosyluronate)-(1→4)-(2-N-acetyl-2-deoxy-α/β-d-glucopyranoside (I0S0) that was synthesized (Compound 7, Supplementary Methods). All standards were tagged with [13C6]aniline (Sigma/Aldrich). Samples were then analyzed by liquid chromatography-mass spectrometry using an LTQ Orbitrap Discovery electrospray ionization mass spectrometer (Thermo Scientific) equipped with quaternary high-performance liquid chromatography pump (Finnigan Surveyor MS pump) and a reverse-phase capillary column as previously described13 (link).
Lawrence R., Brown J.R., Al-Mafraji K., Lamanna W.C., Beitel J.R., Boons G.J., Esko J.D, & Crawford B.E. (2012). Disease-Specific Non-Reducing End Carbohydrate Biomarkers for Mucopolysaccharidoses. Nature chemical biology, 8(2), 197-204.
Publication 2011
Acetic Acid Amination Amines aniline Capillaries Disaccharides High-Performance Liquid Chromatographies Liquid Chromatography Mass Spectrometry Methanol N-acetylgalactosamine 4-sulfate N-acetylgalactosamine 6-sulfate oxytocin, 1-desamino-(O-Et-Tyr)(2)- propionic anhydride Sulfate, Glucosamine Sulfoxide, Dimethyl
2
Neoglycoprotein Synthesis and Antibody Production
A neoglycoprotein (XXXG-BSA) was prepared by coupling a heptasaccharide containing 3 xylosyl and 4 glucosyl residues (XXXG, Megazyme, Bray, Ireland) to BSA by reductive amination [42 (link)]. XXXG (30 mg) was dissolved in 1.0 ml of 0.2 M sodium borate buffer pH 9.0. This was followed by the addition of 20 mg BSA and then 30 mg of sodium cyanoborohydride. The mixture was maintained in a water bath at 50°C with occasional mixing. After 24 h the pH was adjusted to pH 4.0 by the addition of 45 μl of 80% (v/v) acetic acid. The solution was then dialysed extensively against distilled water with several changes over 4 days.
Rat immunization, hybridoma preparation and cloning procedures were performed as described previously [34 (link)]. Two male Wistar rats were injected with 100 μg XXXG-BSA in complete Freund's adjuvant administered subcutaneously on day 0, with the same amount administered with incomplete Freund's adjuvant on days 33 and 71. On day 145, a selected rat was given a prefusion boost of 100 μg XXXG-BSA in 1 ml PBS by intraperitoneal injection. The spleen was isolated three days later for isolation of lymphocytes and fusion with rat myeloma cell line IR983F [43 ]. Antibodies were selected by ELISA using tamarind xyloglucan as antigen. Subsequent characterization was by means of a glycan microarray of cell wall polymers [28 (link)] and competitive inhibition ELISAs using the xyloglucan XXXG heptasaccharide from tamarind xyloglucan and a series of related xyloglucan oligosaccharides. A mixture of the XXLG and XLXG octasaccharide isomers and the XLLG nonasaccharide were derived from tamarind xyloglucan as described [44 (link)] and purified by HPLC using Tosoh TSK Gel Amide column (21.5 × 300 mm) eluted with 65% aqueous acetonitrile. Cellotetraose GGGG was prepared by acetolysis of cellulose [45 ] and separated from the mixture of deacetylated oligosaccharides by HPLC as above. The sample of pea xyloglucan was a gift from Marie-Christine Ralet (INRA, Nantes, France). ELISAs were carried out as described previously [6 (link)] and in all cases immobilised antigens were coated at 50 μg/ml. Mannan, tamarind xyloglucan polymers, isoprimeverose and xylose disaccharide were obtained from Megazyme, Bray, Ireland. The selected antibody, an IgG2c, was designated LM15.
Marcus S.E., Verhertbruggen Y., Hervé C., Ordaz-Ortiz J.J., Farkas V., Pedersen H.L., Willats W.G, & Knox J.P. (2008). Pectic homogalacturonan masks abundant sets of xyloglucan epitopes in plant cell walls. BMC Plant Biology, 8, 60.
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Publication 2008
Acetic Acid acetonitrile Amides Amination Antibodies Antigens Bath Buffers cellotetraose Cellulose Cell Wall Disaccharides Enzyme-Linked Immunosorbent Assay Freund's Adjuvant Fusions, Cell High-Performance Liquid Chromatographies Hybridomas Immunoglobulins incomplete Freund's adjuvant Injections, Intraperitoneal isolation Isomerism isoprimeverose Lymphocyte Males Mannans Microarray Analysis Multiple Myeloma Oligosaccharides Polymers Polysaccharides Psychological Inhibition Rats, Wistar sodium borate sodium cyanoborohydride Spleen Tamarindus indica Vaccination xyloglucan Xylose
3
Synthesis of SR9009 and SR9011
Compounds were synthesized by reductive amination of 5-nitro-2-thiophenecarboxaldehyde with 4-chlorobenzylamine and sodium triacetoxyborohydride yielded the secondary amine. A second reductive amination with 1-Boc-pyrrolidine-3-carboxaldehyde yielded the tertiary amine. This compound was treated with trifluoroacetic acid to remove the Boc-protecting group, and then reacted with either ethyl chloroformate (SR9009) or pentyl isocyanate (SR9011) to give the desired products.
Solt L.A., Wang Y., Banerjee S., Hughes T., Kojetin D.J., Lundasen T., Shin Y., Liu J., Cameron M.D., Noel R., Yoo S.H., Takahashi J.S., Butler A.A., Kamenecka T.M, & Burris T.P. (2012). Regulation of Circadian Behavior and Metabolism by Synthetic REV-ERB Agonists. Nature, 485(7396), 62-68.
Publication 2012
Amination Amines ethyl chloroformate Isocyanates pyrrolidine Sodium SR9009 SR9011 t-butyloxycarbonyl group Trifluoroacetic Acid
4
Glycoprotein and Glycopeptide Conjugation
Both glycoproteins and SGP glycopeptides were conjugated to beads using reductive amination. For peptides, 100 µL of AminoLink resin (200 µL of 50% slurry) was incubated with sample in 400 µL buffer (pH 10.0) (40 mM sodium citrate and 20 mM sodium carbonate) at room temperature for 4 hrs with mixing. Then 40 µL of 500 mM sodium cyanoborohydride (1x PBS) was added to incubate for another 4 hrs. After rinsing the resin with 400 µL of 50 mM phosphate buffer (pH 7.4) twice, sample on the solid support were further reduced by adding 50 mM sodium cyanoborohydride (NaCNBH3) in 50 mM phosphate buffer (pH 7.4) at room temperature for 4 hrs with mixing. After incubation, the beads were washed with 1 M Tris-HCl (400 µL, pH 7.6) twice before addition of 400 µL of 1 M Tris-HCl (pH 7.6) in the presence of 50 mM NaCNBH3 to block the unreacted aldehyde sites on the bead surface for 0.5 hrs. For protein conjugation, 2 mg of mucin from porcine stomach, 400 µg RNase B glycoprotein or 20 µL of serum proteins were first denatured in 100 µL solution consisting of 10 µL denaturing buffer (10×) (New England Biolabs) and 70 µL buffer (pH 10.0) for 10 minutes at 100°C before following glycopeptides conjugation procedure. The proteins or peptides immobilized on beads were washed three times with 400 µL of 1 M NaCl and three times with H2O.
Yang S., Li Y., Shah P, & Zhang H. (2013). Glycomic analysis using glycoprotein immobilization for glycan extraction. Analytical chemistry, 85(11), 5555-5561.
Publication 2013
Aldehydes Amination Buffers Cardiac Arrest Glycopeptides Glycoproteins MUC2 protein, human Peptides Phosphates Pigs Proteins Resins, Plant ribonuclease B Serum Proteins sodium carbonate Sodium Chloride Sodium Citrate sodium cyanoborohydride Stomach Tromethamine
5
Ecotin-based Affinity Purification of Trypsinogen
Ecotin is a pan-serine-protease inhibitor from E. coli (18 (link)) that forms a relatively tight complex with trypsinogen and thus can be used for affinity purification of the zymogen (15 (link)). Recombinant ecotin (17 (link)) is overexpressed in the periplasmic space of E. coli and isolated using osmotic shock (19 (link)) followed by trypsin affinity chromatography. Purified ecotin is immobilized on aldehyde activated resin by reductive amination using cyanoborohydride (15 (link)) and loaded into a chromatography column.
Király O., Guan L, & Sahin-Tóth M. (2011). Expression of Recombinant Proteins with Uniform N-Termini. Methods in molecular biology (Clifton, N.J.), 705, 175-194.
Publication 2011
Aldehydes Amination Chromatography Chromatography, Affinity Enzyme Precursors Escherichia coli Osmotic Shock Periplasm Resins, Plant Serine Proteinase Inhibitors Trypsin Trypsinogen

Most recents protocols related to «Amination»

1
Synthesis of Methotrexate Conjugates
Not available on PMC !

Example 7

The synthesis of the methotrexate conjugates is described in (FIG. 12). A short ethylene diamine spacer may be introduced between methotrexate and the oxidized lipid. 6-Bromomethyl-pteridine-2,4-diamine trihydrobromide (BPT.HBr, 23) may be purchased from Ube Industries and coupled with intermediate 24 to produce 25. Compound 25 may be deprotected from tert-Boc followed by ester hydrolysis to produce amine terminated methotrexate (26). Reductive amination of 26 with ALDO (PE) or (PC) may be performed as described earlier to produce methotrexate prodrugs (27).

US11872313B2. Prodrug compositions, prodrug nanoparticles, and methods of use thereof (2024-01-16). Washington University [US]. Inventors: Gregory M. Lanza [US], Dipanjan Pan [US].
Full text: Click here
Patent 2024
Amination Amines Anabolism Diamines Esters Ethylenediamines Hydrolysis Lipids Methotrexate Prodrugs Pteridines TERT protein, human
2
Synthesis of Platinum-Based Anti-Cancer Prodrugs
Not available on PMC !

Example 6

For the synthesis of platinum based anti cancer prodrugs, two approaches may be followed. The first approach (FIG. 10) may involve the preparation of an amine terminated cis platin (9) followed by conjugation with oxidized lipids. The coupling intermediate produced from the amidation reaction of compound 8 with mono Boc-ethylenediamine in presence of HATU/DIPEA, may be subjected to deprotection to produce compound 9. Compound 9 may undergo reductive amination with ALDO PC in methanol to generate cis platin prodrug-1 (10).

A second approach (FIG. 11) may involve the synthesis of an analogue bearing hydrophobically modified chelating diamines. Cis-platin intermediate 16 may be obtained in three steps from compound 13. Intermediate 16 may be subjected to complexation with K2PtCl4 by maintaining the pH of the resulting solution at pH 6-7. Finally, compound 13 may undergo reductive amination with ALDO (PC) or (PE) to produce cis platin prodrug-2 (18).

US11872313B2. Prodrug compositions, prodrug nanoparticles, and methods of use thereof (2024-01-16). Washington University [US]. Inventors: Gregory M. Lanza [US], Dipanjan Pan [US].
Full text: Click here
Patent 2024
Amination Amines Anabolism CISH protein, human Cisplatin Diamines DIPEA Ethylenediamines Lipids Malignant Neoplasms Methanol Platinum Prodrugs SOCS2 protein, human
3
Reductive Amination of Peptide Intermediates
Not available on PMC !

Example 24

A general peptide coupling with FMOC-amino acids and HATU, and the intermediate MMAF on Cl-trityl resin was prepared as previously described (WO 2009117531A1). Aldehyde (1.4 mmol, 2 equiv) was dissolved in a 10 mL solution of 1% (V/V) AcOH in DMF, followed by the addition of NaBH3CN (1.2 mmol, 1.8 equiv). The solution was added to a syringe with a PET frit containing resin (1 g, 0.7 mmol/g), and the mixture is agitated for about 2 h. The resin was filtered, washed with DMF, DCM and ethyl ether, and dried in a vacuum desiccator.

A solution of 20% (V/V) HFIP in DCM was added to the resin for 1 h and filter. Resin was washed with DCM and the combined organic layers were dried in vacuo. Samples were dissolved for UPLC analysis and preparative HPLC.

The following compounds were prepared according to the general procedures of Part B.

US11857565B2. Hydrophobic Auristatin F compounds and conjugates thereof (2024-01-02). SEAGEN INC. [US]. Inventors: Svetlana O. Doronina [US], Philip Moquist [US].
Full text: Click here
Patent 2024
Aldehydes Amination Ethyl Ether High-Performance Liquid Chromatographies N(alpha)-fluorenylmethyloxycarbonylamino acids Peptides Resins, Plant Syringes Vacuum
4
Paclitaxel Prodrug Synthesis and Purification
Not available on PMC !

Example 4

Paclitaxel prodrug was synthesized following a five-step synthesis process and purified by column chromatography (FIG. 8). Briefly, commercially available paclitaxel (Avachem Scientific, Inc.) was treated with succinic anhydride in the presence of pyridine to give 2′-succinyl paclitaxel. NHS ester (6) of this intermediate may be obtained by reaction with N-succinimidyl diphenylphosphate (SDPP). The ester was treated with an excess of mono-Boc-ethylene diamine at low temperature followed by deprotection of the tert-Boc. A flexible, linear diamine (1,3-diamino propane) was chosen to reduce the steric hindrance. Finally, the paclitaxel amine was subjected to reductive amination with ALDO PC (or PE) to produce paclitaxel prodrugs (7).

US11872313B2. Prodrug compositions, prodrug nanoparticles, and methods of use thereof (2024-01-16). Washington University [US]. Inventors: Gregory M. Lanza [US], Dipanjan Pan [US].
Full text: Click here
Patent 2024
Amination Amines Anabolism Chromatography Cold Temperature Diamines Esters Ethylenediamines Paclitaxel Prodrugs Propane Pyridines succinic anhydride TERT protein, human
5
Asymmetric Synthesis of Bortezomib Prodrug
Not available on PMC !

Example 8

The asymmetric synthesis of bortezomib-prodrug (FIG. 13) may involve the preparation of intermediate-1 (N-sulfinyl α-amino boron pinacolato complex) by following published methods. Selective removal of the N-sufinyl group under mild acidic conditions may produce the amine hydrochloride (intermediate 2), which may then be coupled with N-Boc-L-phenylalanine by a TBTU/DIPEA mediated reaction protocol. Intermediate-3 (amine hydrochloride) may then undergo coupling with the commercially available 3-am inopyrazine-2-carboxylic acid to produce the pinacol boronate of bortezomib. This may subsequently be hydrolyzed under biphasic conditions utilizing iso-butylboronic acid as a pinacol sequestering agent. Finally the intermediate-4 may undergo a sodium cyanoborohydride mediated reductive amination with ALDO (PC) in presence of catalytic amounts of TFA to produce bortezomib prodrug.

US11872313B2. Prodrug compositions, prodrug nanoparticles, and methods of use thereof (2024-01-16). Washington University [US]. Inventors: Gregory M. Lanza [US], Dipanjan Pan [US].
Full text: Click here
Patent 2024
Acids Amination Amines Anabolism Boron Bortezomib Carboxylic Acids Catalysis DIPEA n-butylboronic acid Phenylalanine pinacol Prodrugs Sequestering Agents sodium cyanoborohydride

Top products related to «Amination»

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Ltq orbitrap discovery by Thermo Fisher Scientific
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The LTQ Orbitrap Discovery is a hybrid mass spectrometer that combines a linear ion trap (LTQ) with an Orbitrap mass analyzer. It provides high-resolution, accurate mass measurement capabilities for advanced analytical applications.
2
2 methylpyridine borane complex by Merck Group
Sourced in United States, Germany
2-Methylpyridine borane complex is a chemical compound used in laboratory settings. It serves as a reducing agent and a source of borane in chemical reactions and synthesis processes.
3
D galactose by Merck Group
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D-galactose is a monosaccharide carbohydrate. It is a constituent of many natural polysaccharides, including lactose, cerebrosides, and gangliosides. D-galactose can be used as a laboratory reagent.
4
Sodium periodate by Merck Group
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Sodium periodate is a chemical compound with the formula NaIO4. It is a white, crystalline solid that is soluble in water. Sodium periodate serves as an oxidizing agent in various applications.
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Ribitol by Merck Group
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Ribitol is a sugar alcohol found naturally in various organisms. It is a white, crystalline solid that is soluble in water. Ribitol has the chemical formula C₅H₁₂O₅.
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Mwco 3500 dialysis tubing by Serva Electrophoresis
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MWCO 3500 dialysis tubing is a laboratory equipment used for dialysis, a process of separating molecules based on their size. The tubing has a molecular weight cut-off (MWCO) of 3500 Daltons, which means it can retain molecules larger than 3500 Daltons while allowing smaller molecules to pass through.
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Sodium cyanoborohydride by Merck Group
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Sodium cyanoborohydride is a reducing agent used in various laboratory applications. It is a white crystalline solid that reacts with carbonyl compounds to produce reduced products. The core function of sodium cyanoborohydride is to facilitate chemical reactions and transformations in controlled laboratory settings.
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Dimethyl sulfoxide (dmso) by Merck Group
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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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Poly l lysine (pll) by Merck Group
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Poly-L-lysine is a synthetic polymer composed of the amino acid L-lysine. It is commonly used as a coating agent for various laboratory applications, such as cell culture and microscopy. Poly-L-lysine enhances the attachment and growth of cells on surfaces by providing a positively charged substrate.
10
α d n acetylgalactosaminyl 1 3 galactose by Dextra Laboratories
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α-D-N-Acetylgalactosaminyl 1–3 galactose is a carbohydrate compound used in biochemical research. It serves as a structural component and building block for various biomolecules.

More about "Amination"

Amination is the process of introducing an amino group (-NH2) into a chemical compound, a crucial reaction in organic synthesis to modify molecular structure and properties.
This process can be achieved through various methods, such as nucleophilic addition, reductive amination, or direct amination.
The resulting aminated compounds have diverse applications in pharmaceuticals, agrochemicals, dyes, and other specialized materials.
Researchers can optimize their amination protocols using AI-driven comparisons to locate the best procedures from literature, preprints, and patents, improving reproducibility and accuracy.
PubCompare.ai offers streamlined, data-driven research to help scientists overcome the manual challenges of protocol comparisons and enhance their amination studies.
The LTQ Orbitrap Discovery is a powerful mass spectrometry instrument that can provide valuable insights into the characterization of aminated compounds. 2-Methylpyridine borane complex is a common reducing agent used in reductive amination reactions, while D-galactose and Sodium periodate are often employed in the synthesis of aminated carbohydrates.
Ribitol, a sugar alcohol, and MWCO 3500 dialysis tubing can be utilized in the purification and isolation of aminated molecules.
Sodium cyanoborohydride is another widely used reagent in reductive amination, and DMSO is a versatile solvent often employed in amination reactions.
Poly-L-lysine can serve as a substrate for amination, and α-D-N-Acetylgalactosaminyl 1–3 galactose is a disaccharide that may be functionalized through amination.
Researchers can leverage these insights and tools to optimize their amination protocols, leading to improved reproducibility, accuracy, and ultimately, advancements in the field of organic synthesis and its various applications.