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Propargylamine

Propargylamine is a versatile organic compound with a triple bond in its structure.
It is widely used in various chemical reactions and synthetic procedures, particularly in the synthesis of pharmaceuticals and other bioactive molecules.
The PubCompare.AI tool can help researchers optimize their Propargylamine research by providing easy access to relevant protocols from literature, pre-prints, and patents, while leveraging AI-driven comparisons to identify the best procedures and products.
This can enhance the reproducibility and accuracy of Propargylamine studies, leading to more reliable results and advancements in the field.
Researchers can utilize this powerful tool to streamline their Propargylamine research and make more informed decisions throughout the process.

Most cited protocols related to «Propargylamine»

1
Synthesis of Clickable Fluorescent Probes
Cited 3 times
Two fluorophores, 7-(dimethylamino)-coumarin-4-acetic acid (DMACA, prepared according to literature procedures52 , 53 (link)) and 7-nitrobenzofurazan (NBD, Sigma–Aldrich), were functionalized with an alkyne substituent (Scheme 2) so that they could be coupled to the linezolid–azide analogue 9 by click chemistry. DMACA 23 was reacted with propargylamine in the presence of HATU as coupling agent to give DMACA linked alkyne 24. NBD linked alkyne 26 was prepared by a substitution reaction from NBD-Cl (4-chloro-7-nitrobenzofurazan) 25 by an improved method based on that previously reported in the literature.54 The use of Cs2CO3 in THF for the substitution gave improved yields compared to aqueous NaHCO3 in MeOH.

Synthesis of alkyne-functionalised fluorophores. Reagents and conditions: (i) propargylamine, HATU, DIPEA, DMF rt; (ii) propargylamine, Cs2CO3, THF.

Phetsang W., Blaskovich M.A., Butler M.S., Huang J.X., Zuegg J., Mamidyala S.K., Ramu S., Kavanagh A.M, & Cooper M.A. (2014). An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants. Bioorganic & Medicinal Chemistry, 22(16), 4490-4498.
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Publication 2014
4-Chloro-7-nitrobenzofurazan Acetic Acid Alkynes Azides Bicarbonate, Sodium Coumarins DIPEA Linezolid propargylamine
2
Synthesis of HA-Ub Probes from HAUb75-MESNa
Cited 3 times
The construct pTYB-HAUb, comprising the sequences of the human Ub (lacking Gly 76), an intein and a chitin binding domain, plus an HA tag, was used to synthesize HAUb75-MESNa as described previously (Borodovsky et al., 2002 (link)). Briefly, Ub–intein–chitin domain fusion protein was expressed in Escherichia coli (18 h induction with 0.4 mM IPTG at 17°C). Cell pellets were resuspended in 50 mM HEPES, pH 7.4, 150 mM NaCl, and 0.5 mM TCEP and lysed in a high-pressure homogenizer. The cleared cell extract was loaded onto a 15 ml chitin bead (New England Biolabs) column at a flow rate of 0.5 ml/min. The column was washed with 60 ml of lysis buffer followed by 25 ml of lysis buffer containing 50 mM β-mercaptoethanesulfonic acid sodium salt (MESNa) and incubated overnight at 37°C for the induction of on-column cleavage. HAUb75-MESNa thioester was eluted with 25 ml of lysis buffer and concentrated: approximately 2.5 mg of protein was recovered from a 1-L culture. The N-terminal Met of the HA-tag was frequently processed off during expression, resulting in a mixture of two proteins that behaved identically in labeling experiments.
To synthesize the HA-UbC2Br or HA-UbPA probes, 0.2 mM of 2-bromoethylamine or 250 mM propargylamine was added to a solution of HAUb75-MESNa (1–2 mg/ml) in 500 μl of column buffer, respectively. pH was carefully adjusted to 8 with NaOH, and after 20 min shaking at 1,400 rpm, at room temperature, 100 μl of 2.0 M aqueous HCl was added and the resultant reaction mixture was promptly transferred to a PD10 gravity column for buffer exchange, according to the manufacturer's instructions.
The probe was then aliquoted and frozen at −80°C for storage (no significant deterioration is observed for several months of storage except for HA-UbC2Br, which is prone to hydrolysis). All HA-Ub-derived probes were analyzed by liquid chromatography mass spectrometry (LC-MS) using a 1290 UPLC (Agilent) coupled to a 6560 quadrupole time-of-flight (QToF) mass spectrometer (Agilent) to monitor the reaction and the product detected by [M+H]+ = 10,197.6221, with >90% purity.
Pinto-Fernández A., Davis S., Schofield A.B., Scott H.C., Zhang P., Salah E., Mathea S., Charles P.D., Damianou A., Bond G., Fischer R, & Kessler B.M. (2019). Comprehensive Landscape of Active Deubiquitinating Enzymes Profiled by Advanced Chemoproteomics. Frontiers in Chemistry, 7, 592.
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Publication 2019
Buffers Cell Extracts Cells Chitin Chitin Binding Domain Coenzyme M Cytokinesis Escherichia coli Freezing Gravity HEPES Homo sapiens Hydrolysis Intein Isopropyl Thiogalactoside Liquid Chromatography Mass Spectrometry Mesna Pellets, Drug Pressure propargylamine Proteins Sodium Sodium Chloride Staphylococcal Protein A tris(2-carboxyethyl)phosphine
3
Synthesis and Characterization of Modified RNA Oligonucleotides
Cited 2 times
RNA oligonucleotides were synthesized on a ABI 394 synthesizer (DNA/Peptide Core Facility, University of Utah, Salt Lake City) using 5′-DMTr protected β-cyanoethyl phosphoramidites on a 1.0 mmol scale with coupling times of 25 min for increased coupling efficiency of amidites 6 and 7. All RNAs were deprotected as previously described.46 The RNA oligonucleotides containing ethynyl and propargylamine modifications were gel-purified and quantified as previously described.14 (link) The identity of the RNAs was confirmed by MALDI mass spectrometry.
List of mass values, [M+H]+, for the RNA containing propargylamine and ethynyl modifications: Propargylamine: Calc. 3929.5, Obs. 3929.5; Ethynyl: Calc. 3900.4, Obs. 3900.5.
Ibarra-Soza J.M., Morris A.A., Jayalath P., Peacock H., Conrad W.E., Donald M.B., Kurth M.J, & Beal P.A. (2012). 7-Substituted 8-aza-7-deazaadenosines for modification of the siRNA major groove. Organic & biomolecular chemistry, 10(32), 6491-6497.
Publication 2012
Mass Spectrometry Oligonucleotides Peptides phosphoramidite propargylamine Sodium Chloride Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
4
Functionalized HBPE Nanoparticle Synthesis
Cited 2 times
Alternatively, different surface functional HBPE nanoparticles (10, 11 and 12) can be prepared from carboxylated HBPE nanoparticles (9, SI Scheme S1) using water-soluble EDC [1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride] chemistry, following previously reported method.27 (link) Briefly, to a solution of carboxylated HBPE nanoparticles (9, 1.0 mole) in MES buffer, a solution of EDC (10 mmol) and NHS (10 mmol) was added followed by 3 min incubation at room temperature. Ethylenediamine, propargylamine or aminopropylazide (10 mmol) in DMF were then added drop-wise and continued for 3 h to obtain 10, 11 or 12, respectively.
Santra S., Kaittanis C, & Perez J.M. (2010). Aliphatic hyperbranched polyester: A new building block in the construction of multifunctional nanoparticles and nanocomposites**. Langmuir : the ACS journal of surfaces and colloids, 26(8), 5364-5373.
Publication 2009
Buffers Carbodiimides Ethylenediamines Nevus propargylamine
5
Synthesis of Clickable Fluorescent Probes
Cited 2 times
We prepared AHA and the triazole ligand as described previously47 (link). We prepared the TexasRed–PEO2–Alkyne by dissolving TexasRed–PEO2–propionic acid succinimidyl ester (Biotium Inc.) in excess neat propargylamine (Sigma–Aldrich). After 30 min, we added the solution dropwise to anhydrous diethyl ether. We collected the resulting precipitate by centrifugation (5 min, 10°C, 10.000 × g). Then, we washed the precipitate three times with anhydrous diethyl ether, dried and characterized it by ion spray MS to confirm the formation of the product with a molecular weight of 802.90 g/mol (Supplementary Fig. 1a). We synthesized the azide–bearing fluorescein tag in a similar way using the amine–reactive 5–carboxyfluorescein–PEO8–propionic acid succinimidyl ester (Biotium Inc.) and 3–azidopropan–1–amine20 (link) to yield a product with a molecular weight of 881.20 g/mol (Supplementary Fig. 1b).
Dieterich D.C., Hodas J.J., Gouzer G., Shadrin I.Y., Ngo J.T., Triller A., Tirrell D.A, & Schuman E.M. (2010). In situ visualization and dynamics of newly synthesized proteins in rat hippocampal neurons. Nature neuroscience, 13(7), 897-905.
Publication 2010
Alkynes Amines Azides carboxyfluorescein Centrifugation Esters Ethyl Ether Fluorescein Ligands propargylamine propionic acid Triazoles

Most recents protocols related to «Propargylamine»

1
Synthesis of Fmoc-Protected Alkyne Amino Acids
Fmoc-Propargylamine and Fmoc-Mba (Fmoc-2-methyl-3-butyn-2-amine) were prepared accordingly as described before [18 (link)]. The structures of both compounds, as well as the spectra of their 1H and 13C NMR analysis, can be found in the Supplementary Materials (Figures S5 and S6). 1H and 13C NMR spectra were recorded on a Bruker 500 MHz spectrometer (Bruker Corporation, Billerica, MA, USA).
Fmoc-Propargylamine (5): 1H NMR (DMSO-d6, 500 MHz) δ 7.89 (2H, d, J = 7.5 Hz, Fmoc H4 and H5), 7.78 (1H, t, J = 5.5 Hz, NH), 7.69 (2H, d, J = 7.0 Hz, Fmoc H1 and H8), 7.41 (2H, td, J = 7.5, 0.5 Hz, Fmoc H3 and H6), 7.33 (2H, td, J = 7.5, 1.0 Hz, Fmoc H2 and H7), 4.32 (2H, d, J = 7.0 Hz, Fmoc CH2), 4.22 (1H, t, J = 6.7 Hz, Fmoc H9), 3.78 (2H, dd, J = 6.0, 2.5 Hz, H3), 3.11 (1H, t, J = 2.5 Hz, H1);
13C NMR (DMSO-d6, 125 MHz) δ 155.92 (C), 143.81 (C), 143.81 (C), 140.73 (C), 140.73 (C), 127.64 (CH), 127.64 (CH), 127.08 (CH), 127.08 (CH), 125.15 (CH), 125.15 (CH), 120.13 (CH), 120.13 (CH), 81.38 (C), 73.05 (CH), 65.67 (CH2), 46.61 (CH), 29.78 (CH2).
Fmoc-Mba (6): 1H NMR (DMSO-d6, 500 MHz) δ 7.89 (2H, d, J = 7.5 Hz, Fmoc H4 and H5), 7.73 (2H, d, J = 7.5 Hz, Fmoc H1 and H8), 7.58 (1H, s, NH), 7.41 (2H, td, J = 7.5, 0.5 Hz, Fmoc H3 and H6), 7.33 (2H, td, J = 7.5, 1.0 Hz, Fmoc H2 and H7), 4.27 (2H, d, J = 5.5 Hz, Fmoc CH2), 4.20 (1H, t, J = 6.5 Hz, Fmoc H9), 3.07 (1H, s, H1), 1.47 (6H, s, Me groups);
13C NMR (DMSO-d6, 125 MHz) δ 154.37 (C), 143.90 (C), 143.90 (C), 140.72 (C), 140.72 (C), 127.62 (CH), 127.62 (CH), 127.06 (CH), 127.06 (CH), 125.28 (CH), 125.28 (CH), 120.10 (CH), 120.10 (CH), 88.10 (C), 88.10 (C), 70.77 (CH), 65.19 (CH2), 46.68 (CH3), 46.13 (CH3), 29.14 (C).
Fedorczyk B., Redkiewicz P., Matalińska J., Piast R., Kosson P, & Wieczorek R. (2024). Chirality and Rigidity in Triazole-Modified Peptidomimetics Interacting with Neuropilin-1. Pharmaceuticals, 17(2), 190.
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Publication 2024
2
Bortezomib and P8 Modulation of Cellular Proteome
HeLa cells were seeded and cultured in 35 mm confocal dish and 25 cm2 culture flask for fluorescence and gel analysis, respectively before treatment of Bortezomib (0.8 µm) and P8 (5 µm) for 24 h. For fluorescence analysis, cells were next fixed and permeabilized with 4% formaldehyde and 0.1% Triton X‐100 at room temperature consistently for 30 min. The cells were then added with propargylamine (10.0 mm) before white light illumination for 20 min. Freshly premixed click solution (1.7 mm TBTA, 50.0 mm CuSO4, 50.0 mm TCEP, and 50.0 mm BODIPY‐N3) was finally added to pretreated cells and reacted for 1 h. Cells were washed with PBS three times to remove unreacted click solution and treated with Hoechst 33342 before imaging with Olympus FV1000 FluoViewTM confocal microscope. For gel analysis, cells were incubated with propargylamine (10.0 mm) before white light illumination for 20 min. Next, cells were ultrasonic lysed with 1% SDS followed by reaction with newly prepared click solution (1.7 mm TBTA, 50.0 mm CuSO4, 50.0 mm TCEP, and 50.0 mm TMR‐N3). The obtained proteome samples were precipitated with acetone before gel analysis.
Feng H., Zhao Q., Zhao N., Liang Z., Huang Y., Zhang X., Zhang L, & Liu Y. (2024). A Cell‐Permeable Photosensitizer for Selective Proximity Labeling and Crosslinking of Aggregated Proteome. Advanced Science, 11(18), 2306950.
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Publication 2024
3
Triple Protein Labeling via Enzymatic Conjugation
Not available on PMC !
Protein triple labelling was demonstrated with CTC-445.2d modified with an N-terminal LPETG, an internal KL-tag and a C-terminal NGLH motif. In the first step, 50 µM protein was C-terminally labelled using 1 µM OaAEP1 in 100 mM HEPES buffer, pH 7, containing 20 mM propargylamine. Next, the reaction was diluted tenfold with 100 mM HEPES buffer, pH 8, and bound to Ni-NTA. After collecting the flowthrough, the protein was N-terminally cleaved with SrtA-7M in the presence of 5 mM propargylamine. Next the protein was buffer-exchanged into 100 mM HEPES buffer, pH 8, using NAP-5, and N-terminally labelled in a reaction containing 30 µM protein, 450 µM TAMRA-LPETGGH and 1 µM SrtA-7M. The SrtA-7M was subsequently removed by rebinding to Ni-NTA and collecting the flowthrough. Next, the reaction was buffer-exchanged via NAP-5 into 100 mM HEPES buffer, pH 8, and the KL-tag labelling was carried out in a reaction containing 50 µM protein, 1 mM biotin-RNGLH, 1 mM NiSO 4 and 1 µM OaAEP1 for 4 h at 25 °C. https://doi.org/10.1038/s41557-024-01520-1
Rehm F.B.H., Tyler T.J., Zhou Y., Huang Y.H., Wang C.K., Lawrence N., Craik D.J, & Durek T. (2024). Repurposing a plant peptide cyclase for targeted lysine acylation. Nature chemistry.
Publication 2024
4
Synthesis of Propargylamine Peptide Conjugates
To the solution of peptide acid (1.0 equiv.) obtained from resins 7, 8 or 19 and HATU (4.0 equiv.) dissolved in DMF/CH2Cl2 (1 : 1, peptide concentration 0.02 M), propargylamine (3.0 equiv.) and Et3N (5.0 equiv.) were added. After stirring for 1 h, CH2Cl2 was removed from the reaction mixture under reduced pressure. The remaining mixture was purified by HPLC with a Vydac C18 column.
Tsai C.L., Chang J.W., Cheng K.Y., Lan Y.J., Hsu Y.C., Lin Q.D., Chen T.Y., Shih O., Lin C.H., Chiang P.H., Simenas M., Kalendra V., Chiang Y.W., Chen C.H., Jeng U.S, & Wang S.K. (2024). Comprehensive characterization of polyproline tri-helix macrocyclic nanoscaffolds for predictive ligand positioning. Nanoscale Advances, 6(3), 947-959.
Publication 2024
5
Cellular Labeling with MG Probes
Prior to the labeling process, cells were washed with Hank’s balanced salt solution (HBSS) to remove any residual medium. Subsequently, cells were treated with freshly prepared MG probes in a DMEM solution for 20 min. The cells were rinsed once with HBSS and further incubated with propargylamine (PA) in HBSS for 3 min, followed by 660 nm light irradiation. The cells underwent two additional washes with HBSS and were ready for downstream procedures, such as RNA isolation, protein extraction or slide preparation for confocal microscopy imaging.
Li L., Han J., Lo H.Y., Tam W.W., Jia H., Tse E.C., Taliaferro J.M, & Li Y. (2024). Symmetry-breaking malachite green as a near-infrared light-activated fluorogenic photosensitizer for RNA proximity labeling. Nucleic Acids Research, 52(7), e36.
Publication 2024

Top products related to «Propargylamine»

1
Propargylamine by Merck Group
Sourced in United States, Germany
Propargylamine is a laboratory reagent that functions as a precursor for the synthesis of various organic compounds. It is a colorless, volatile liquid with a distinctive odor. Propargylamine is commonly used in organic synthesis, particularly in the preparation of heterocyclic compounds and other nitrogen-containing molecules.
2
Propargylamine hydrochloride by Merck Group
Propargylamine hydrochloride is a chemical compound used as a laboratory reagent. It is a white crystalline solid that is soluble in water and various organic solvents. The compound is commonly used in organic synthesis reactions and as a precursor for the synthesis of other compounds.
3
Chitin resin by New England Biolabs
Sourced in United States
Chitin resin is a chromatography medium used for the purification of proteins and other biomolecules. It is derived from the exoskeletons of crustaceans and has a high affinity for proteins containing chitin-binding domains.
4
Dimethyl sulfoxide (dmso) by Merck Group
Sourced in United States, Germany, United Kingdom, China, Italy, Sao Tome and Principe, France, Macao, India, Canada, Switzerland, Japan, Australia, Spain, Poland, Belgium, Brazil, Czechia, Portugal, Austria, Denmark, Israel, Sweden, Ireland, Hungary, Mexico, Netherlands, Singapore, Indonesia, Slovakia, Cameroon, Norway, Thailand, Chile, Finland, Malaysia, Latvia, New Zealand, Hong Kong, Pakistan, Uruguay, Bangladesh
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.
5
Sodium azide by Merck Group
Sourced in United States, Germany, United Kingdom, France, Italy, Sao Tome and Principe, Spain, Australia, Switzerland, Canada, Macao, Ireland, China, Brazil, Japan, Poland, New Zealand, India, Israel, Czechia, Denmark, Norway, Belgium
Sodium azide is a chemical compound commonly used in laboratory applications. It functions as a preservative and acts as a source of the azide ion, which can be utilized in various experimental and analytical procedures. This product is intended for use by qualified professionals in controlled laboratory settings.
6
N n dimethylformamide (dmf) by Merck Group
Sourced in United States, Germany, United Kingdom, China, Italy, Canada, India, Australia, Japan, Spain, Singapore, Sao Tome and Principe, Poland, France, Switzerland, Macao, Chile, Belgium, Czechia, Hungary, Netherlands
N,N-dimethylformamide is a clear, colorless liquid organic compound with the chemical formula (CH3)2NC(O)H. It is a common laboratory solvent used in various chemical reactions and processes.
7
Vivaspin 20 column by Sartorius
Sourced in Germany
The VIVASPIN 20 Columns are centrifugal concentrators used for concentrating and desalting small sample volumes. They feature a polyethersulfone (PES) membrane that allows selective retention of molecules above a specific molecular weight cut-off.
8
Sodium ascorbate by Merck Group
Sourced in United States, Germany, France, United Kingdom
Sodium ascorbate is a water-soluble salt of ascorbic acid (vitamin C). It serves as a source of vitamin C for various laboratory and research applications.
9
Ascorbic acid by Lumiprobe
Ascorbic acid is a chemical compound used as a laboratory reagent. It is a white, crystalline solid that is soluble in water and has a sour taste. Ascorbic acid is a reducing agent and has various applications in chemical analysis and research.
10
N n diisopropylethylamine dipea by Merck Group
Sourced in United States, Germany, United Kingdom, France
N,N-diisopropylethylamine (DIPEA) is a volatile, colorless liquid organic compound commonly used as a base and a catalyst in various chemical reactions. It is a tertiary amine with the molecular formula (CH3)2CH-CH2-N(CH3)2. DIPEA is a commonly used reagent in organic chemistry and biochemistry.

More about "Propargylamine"

Propargylamine, also known as 2-propynylamine or propargylic amine, is a versatile organic compound with a triple bond (alkyne) in its structure.
This reactive functional group makes Propargylamine a valuable building block in various chemical reactions and synthetic procedures, particularly in the synthesis of pharmaceuticals and other bioactive molecules.
Propargylamine hydrochloride, a salt form of the compound, is also commonly utilized in research and industrial applications.
Chitin resin, a polymer derived from the exoskeletons of crustaceans, can be used in combination with Propargylamine for selective enrichment and isolation of biomolecules.
DMSO (Dimethyl sulfoxide) is a widely used solvent that can be employed in Propargylamine-based reactions and syntheses.
Sodium azide, another important reagent, can react with Propargylamine to produce various nitrogen-containing heterocyclic compounds.
N,N-dimethylformamide (DMF) is another commonly used solvent in Propargylamine chemistry, particularly in the preparation of Propargylamine-derived compounds.
VIVASPIN 20 Columns, a type of ultrafiltration device, can be utilized for the purification and concentration of Propargylamine-containing solutions.
Sodium ascorbate and ascorbic acid (vitamin C) are antioxidants that can be employed in Propargylamine-based reactions to prevent oxidation and improve reaction conditions.
N,N-diisopropylethylamine (DIPEA), also known as Hünig's base, is a versatile organic base that can be used in conjunction with Propargylamine in various synthetic transformations.
The PubCompare.AI tool can be invaluable for researchers working with Propargylamine, as it provides easy access to relevant protocols from literature, pre-prints, and patents, while leveraging AI-driven comparisons to identify the best procedures and products.
This can enhance the reproducibility and accuracy of Propargylamine studies, leading to more reliable results and advancements in the field.
Researchers can utilize this powerful tool to streamline their Propargylamine research and make more informed decisions throughout the process.