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Chemical Structure| 14044-63-4 Chemical Structure| 14044-63-4
Chemical Structure| 14044-63-4

*Storage: Sealed in dry,2-8°C.

But-3-yn-1-amine

CAS No.: 14044-63-4

4.5 *For Research Use Only !

Cat. No.: A902473 Purity: 98%

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Product Citations

Product Citations

Wolfer, Jamison D ; Minkoff, Benjamin B ; Burch, Heather L , et al.

Abstract: Protein footprinting is a useful method for studying protein higher order structure and conformational changes induced by interactions with various ligands via addition of covalent modifications onto the protein. Compared to other methods that provide single amino acid-level structural resolution, such as cryo-EM, X-ray diffraction, and NMR, mass spectrometry (MS)-based methods can be advantageous as they require lower protein amounts and purity. As with other MS-based proteomic methods, such as post-translational modification analysis, enrichment techniques have proven necessary for both optimal sensitivity and sequence coverage when analyzing highly complex proteomes. Currently used reagents for footprinting via covalent labeling, such as hydroxyl radicals and carbodiimide-based methods, do not yet have a suitable enrichment method, limiting their applicability to whole proteome analysis. Here, we report a method for enrichable covalent labeling built upon the GEE/EDC system commonly used to covalently label aspartic acid and glutamic acid residues. Novel labeling reagents containing alkynyl functionality can be "clicked" to any azido-containing molecule with copper-catalyzed azide−alkyne cycloaddition (CuAAC), allowing for enrichment or further labeling. Multiple azide- and alkyne-containing GEE-like molecules were tested, and the most efficient method was determined to be the EDC-facilitated coupling of glycine propargyl amide (GPA) to proteins. The pipeline we report includes clicking via CuAAC to a commercially available biotin-azide containing a photocleavable linker, followed by enrichment using a streptavidin resin and subsequent cleavage under ultraviolet light. The enrichment process was optimized through the screening of clickable amines, coupling reagents, and enrichment scaffolds and methods with pure model proteins and has also been applied to complex mixtures of proteins isolated from the model plant, Arabidopsis thaliana, suggesting that our method may ultimately be used to measure protein conformation on a proteomic scale.

Product Details of [ 14044-63-4 ]

CAS No. :14044-63-4
Formula : C4H7N
Linear Structure Formula :HCC(CH2)2NH2
M.W : 69.11
SMILES Code : C#CCCN
MDL No. :MFCD09997741
InChI Key :XSBPYGDBXQXSCU-UHFFFAOYSA-N
Pubchem ID :10034574

Safety of [ 14044-63-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:3(8)
UN#:2733
Packing Group:

Application In Synthesis [ 14044-63-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 14044-63-4 ]

[ 14044-63-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 14044-63-4 ]
  • [ 138165-75-0 ]
  • [ 1454891-39-4 ]
YieldReaction ConditionsOperation in experiment
66% With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 22h;Inert atmosphere; Cooling with ice; General procedure: Alkynylamine (1.5equiv) was added to N-Boc-l-leucine or N-Boc-l-beta-homoleucine (1equiv) and HATU (1.1equiv) in DMF at room temperature under nitrogen. The solutions were cooled on ice and Et3N (3equiv) was added, thereaction mixture was then allowed to reach room temperature and stirred for 22h. The reaction mixture was diluted with EtOAc(30ml), washed with 0.1M HCl (2×10ml), saturated NaHCO3 (10ml), brine (20ml), dried over Na2SO4 and the solvents wereremoved. The crude product was purified by automated flashchromatography (gradient, 0-100% EtOAc in heptane).
  • 2
  • [ 661463-17-8 ]
  • [ 14044-63-4 ]
  • N-(but-3-yn-1-yl)-6-fluoroquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% at 80 - 140℃; 3-Butyn-l -amine (764 mg, 0.91 mL, 1 1.1 mmol, 5 eq.) was mixed with 4-bromo-6- fluoroquinoline (500 mg, 2.21 mmol, 1 eq.) to form a paste, which was heated to 80 C for 1 hour without stirring, the temperature was raised to 140 C and the reaction was left overnight with stirring. After cooling to room temperature, NaOH (1M, 2 mL) was added. The organic product was basified (10% NaOH) and extracted with CH2CI2. The organic extracts were combined, dried (MgS04), filtered and concentrated in vacuo. The crude product was purified by column chromatography (AI2O3, 10%> MeOH in EtOAc), affording N-(but-3-yn-l-yl)-6-fluoroquinolin-4-amine (465 mg, 2.17 mmol, 98%>). Ref: Austin et al, J ACS, 1489-1497 (1958) TLC Rf 0.75 (MeOH/ EtOAc 1 :9, AI2O3) FontWeight="Bold" FontSize="10" H MR (400MHZ, DMSO-de) delta (ppm) 8.41 (d, J=5.1 Hz, 1H, NCH), 7.89-8.08 (m, 1H, FCCHCH), 7.85 (dd, J=9.3, 5.9 Hz, 1H, FCCHCH), 7.53 (td, J=8.7, 2.8 Hz, 1H, FCCHC), 6.54 (d, J=5.4 Hz, 1H, NCHCH), 3.42-3.51 (m, 2H, CH2CH2CCH), 2.90 (t, J=2.6 Hz, 1H, CH2CH2CCH), 2.56 (td, J=7.1 , 2.7 Hz, 2H, CH2CH2CCH) ppm 13CNMR (101 MHz, DMSO-de) delta (ppm) 150.5 (4), 150.2 (7), 149.1 (9), 140.0 (1), 124.6 (2), 1 19.9 (3), 1 13.6 (6), 108.8 (5), 99.4 (8), 72.9 (16), 56.0 (13), 41.8 (11), 18.3 (12) ppm IR (neat) v max 3387 (m), 2830 (m), 663 (s) cm"1 LCMS (ESI+) m/z 215.1 [M+H]+ 11 RMS (ESI+) m/z calcd. 215.0979 m/z meas. 215.0982 [M+H]+ Mpt 148 - 150 C
  • 3
  • [ 14369-81-4 ]
  • [ 14044-63-4 ]
  • [ 37669-78-6 ]
 

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