Recent Advances in Recoverable Systems for the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction (CuAAC). (nih.gov)
This reaction is better termed the Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC). (wikipedia.org)
Herein, we describe an efficient method to prepare organomagnesium intermediates by iodine-magnesium exchange with a turbo Grignard reagent after the phosphazide formation of iodine-substituted azides, enabling facile synthesis of diverse 1,2,3-triazoles by Grignard reactions and following CuAAC reactions. (frontiersin.org)
12. Decoration of Coiled-Coil Peptides with N-Cysteine Peptide Thioesters As Cyclic Peptide Precursors Using Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) Click Reaction. (nih.gov)
The CuAAC Cell Reaction Buffer Kit (BTTAA based) is suitable to perform Copper (Cu(I))-catalyzed Azide-Alkyne Click chemistry reactions (CuAAC) with cells containing metabolically functionalized Alkyne- or Azide modified biomolecules. (jenabioscience.com)
1 Kit provides sufficient amounts to perform 50 CuAAC experiments à 500 μl using 2 mM CuSO 4 (copper source), 10 mM BTTAA (Cu(I)-stabilizing ligand) and 100 mM Na-Ascorbate (reduction reagent) in 100 mM Na-Phosphate reaction buffer. (jenabioscience.com)
Copper ( Cu (I))-catalyzed A zide- A lkyne C lick chemistry reactions ( CuAAC ) describe the reaction of an Azide-functionalized molecule A with a terminal Alkyne-functionalized molecule B that results in a stable conjugate A-B via a Triazole moiety. (jenabioscience.com)
These reactions include copper-catalyzed alkyne-azide cycloaddition (CuAAC), strain-promoted alkyne-azide cycloaddition, inverse electron demand Diels-Alder (IEDDA) reaction, and more. (environmental-expert.com)
AZDye™ 647 Alkyne reacts with azides via a copper-catalyzed click reaction (CuAAC) to form a stable triazole linker. (vectorlabs.com)
The well known 'click chemistry' and especially its flagship, the copper-catalyzed azide-alkyne cycloaddition reaction (CuAAC), is now catch up by such heterogenisation process and copper ions or metals have been grafted or deposited on or into various solids, such as (bio)polymers, charcoal, silica, zeolites, POM or MOF. (rsc.org)
The successful synthesis of an octaazide COSS scaffold allowed for the eightfold conjugation of an octa-RGD peptide via copper(I)-catalyzed alkyne-azide [3+2] cycloaddition (CuAAC) in a water-free system. (tu-darmstadt.de)
A series of novel menadione based triazole hybrids were designed and synthesized by employing copper catalyzed azide-alkyne cycloaddition (CuAAC). (researcher-app.com)
Reactions16
The standard 1,3-cycloaddition between an azide 1,3-dipole and an alkene as dipolarophile has largely been ignored due to lack of reactivity as a result of electron-poor olefins and elimination side reactions. (wikipedia.org)
Some success has been found with non-metal-catalyzed cycloadditions, such as the reactions using dipolarophiles that are electron-poor olefins or alkynes. (wikipedia.org)
Although azides are not the most reactive 1,3-dipole available for reaction, they are preferred for their relative lack of side reactions and stability in typical synthetic conditions. (wikipedia.org)
Similarly the use of organic solvents, copper (I) and inert atmospheres to do the cycloaddition with many polymers makes the "click" label inappropriate for such reactions. (wikipedia.org)
As mentioned above, copper-catalysed click reactions work essentially on terminal alkynes. (wikipedia.org)
Furthermore, click reactions of azides with alkynes enabled synthesizing a wide variety of 1,2,3-triazoles. (frontiersin.org)
Sharpless' first Nobel Prize in Chemistry, awarded in 2001, was for his work on chirally catalyzed oxidation reactions. (genengnews.com)
Alkyne functionalized dyes were used for bioorthogonal click reactions by labeling of metabolically incorporated sugar-azides on the surface of living neuroblastoma cells, which were applied to direct stochastic optical reconstruction microscopy ( d STORM) for the visualization of cell-surface glycans in the nm-range. (degruyter.com)
3. Biocompatible Azide-Alkyne "Click" Reactions for Surface Decoration of Glyco-Engineered Cells. (nih.gov)
4. Rate determination of azide click reactions onto alkyne polymer brush scaffolds: a comparison of conventional and catalyst-free cycloadditions for tunable surface modification. (nih.gov)
19. Copper-chelating azides for efficient click conjugation reactions in complex media. (nih.gov)
By this method, two series of azide group-terminated polyrotaxanes (benzylazide: PRX-Bn-N 3, phenylazide: PRX-Ph-N 3, ) were synthesized for functionalization via click reactions. (beilstein-journals.org)
The PRX-Bn-N 3 and PRX-Ph-N 3 reacted quickly and efficiently with p -( tert -butyl)phenylacetylene via copper-catalyzed click reactions. (beilstein-journals.org)
During the course of these investigations the copper catalyzed azide-alkyne cycloaddition has been used heavily for conjugation reactions involving small molecules and proteins. (umass.edu)
Previously prepared azide terminated polymers were grafted to the multifunctional alkyne core molecules and polymer backbones by copper (I) catalyzed alkyne-azide cycloaddition reactions. (tennessee.edu)
Such rotaxane dendrimers have been synthesized through versatile copper-catalyzed azide-alkyne cycloaddition reactions. (edu.hk)
Reaction16
In the reaction above azide 2 reacts neatly with alkyne 1 to afford the product triazole as a mixture of 1,4-adduct (3a) and 1,5-adduct (3b) at 98 °C in 18 hours. (wikipedia.org)
While the reaction can be performed using commercial sources of copper(I) such as cuprous bromide or iodide, the reaction works much better using a mixture of copper(II) (e.g. copper(II) sulfate) and a reducing agent (e.g. sodium ascorbate) to produce Cu(I) in situ. (wikipedia.org)
The utility of the Cu(I)-catalyzed click reaction has also been demonstrated in the polymerization reaction of a bis-azide and a bis-alkyne with copper(I) and TBTA to a conjugated fluorene based polymer. (wikipedia.org)
This requires protection of the terminal alkyne with a trimethyl silyl protecting group and subsequent deprotection after the radical reaction are completed. (wikipedia.org)
The Cu species undergo metal insertion reaction into the terminal alkynes. (wikipedia.org)
Herein we report the feasible quantitative scale synthesis of photoswitchable alkyne functionalized water-soluble cyanine dyes with absorption wavelengths from ~550 (m=1) to ~650 nm (m=2) which have been used successfully for the bioorthogonal Huisgen-Meldal-Sharpless click reaction on the surface of living cells. (degruyter.com)
5. Chemoselective modification of turnip yellow mosaic virus by Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction and its application in cell binding. (nih.gov)
14. Cyclic Multiblock Copolymers via Combination of Iterative Cu(0)-Mediated Radical Polymerization and Cu(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction. (nih.gov)
The use of Picolyl-Azide reagents instead of conventional Azide reagents can further increase the reaction efficiency and decrease the required final CuSO 4 concentration due to the internal copper chelating moiety. (jenabioscience.com)
Prepare a mix of Alkyne- and Azide functionalized molecules in an appropriate reaction buffer. (jenabioscience.com)
Copper-free azide-alkyne conjugation methods exist, but suffer from drawbacks of their own such as slow reaction rates and difficult targetability. (umass.edu)
In order to maintain the positive aspects of copper free click yet overcome the drawbacks, we have been developing photosensitive probes which upon irradiation rapidly react with azides in a click like reaction. (umass.edu)
The Click-iT EdU Flow Cytometry Assay Kits rely on EdU (5-ethynyl-2´-deoxyuridine), a thymidine analog which is incorporated into DNA during active DNA synthesis, which is then detected using click chemistry, a copper catalyzed covalent reaction between an azide and an alkyne. (selectscience.net)
A synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction proceeds via an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety followed by gold-catalyzed 5- endo - dig cyclization and aromatization. (organic-chemistry.org)
Using the Syrris Asia FLLEX (Flow Liquid Liquid Extraction) module researchers at the Eindhoven University of Technology have demonstrated an efficient extraction method to continuously remove metal catalysts from an azide-alkyne cycloaddition click reaction in flow. (syrris.com)
Additionally, copper(I) is not needed to catalyze the reaction, making SPAAC chemistry preferable when working with live cells that can be poisoned by copper(I). Although the DBCO can react with free sulfhydryl groups under some conditions, it is highly selective for azides. (quantabiodesign.com)
Molecules4
This is followed by the synthesis and characterization of multifunctional alkyne core molecules and random copolymers of polystyrene-co-poly(4-hydroxystyrene) which served as templates for the synthesis of new random copolymers of polystyrene-co-poly(4-propynyloxy)styrene. (tennessee.edu)
The newly formed multifunctional alkyne core molecules and alkyne functionalized random copolymers served as polymer backbones in a "grafting to" strategy. (tennessee.edu)
Strain-promoted alkyne-azide cycloaddition (SPAAC) can also occur with molecules containing DBCO or BCN groups. (medchemexpress.com)
DBCO-dPEG ® 12 -carboxyfluorescein, product number 11812, permits fluorescein labeling of peptides, proteins, and other molecules using strain-promoted azide-alkyne cycloaddition (SPAAC). (quantabiodesign.com)
Triazole4
The azide-alkyne Huisgen cycloaddition is a 1,3-dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3-triazole. (wikipedia.org)
While the copper(I)-catalyzed variant gives rise to a triazole from a terminal alkyne and an azide, formally it is not a 1,3-dipolar cycloaddition and thus should not be termed a Huisgen cycloaddition. (wikipedia.org)
A copper(I)-catalyzed 1,2,3-triazole azide-alkyne click compound is a potent inhibitor of a multidrug-resistant HIV-1 protease variant. (nih.gov)
The highly strained cyclooctyne ring reacts readily with azides to form a stable triazole ring. (quantabiodesign.com)
Synthesis3
Protection of azido groups with di-( tert -butyl)(4-(dimethylamino)phenylphosphine (amphos) and following iodine-magnesium exchange realized the preparation of organomagnesium intermediates, which served in the synthesis of diverse azides by transformation with various electrophiles followed by deprotection with elemental sulfur. (frontiersin.org)
Using a Syrris Asia flow chemistry system researchers at the University of Graz and Universidade de Brasilia have demonstrated a complex, multi-step continuous synthesis of cyclic peptoids using a sequential Ugi multicomponent/Cu-catalysed Azide-Alkyne cycloaddition approach. (syrris.com)
5-AmdU (5-Azidomethyl-2'-deoxyuridine) can be used as a replacement for BrdU (5-Bromo-2'-deoxyuridine) or the copper-catalyst requiring 5-EdU (5-Ethynyl-2'-deoxyuridine) to measure de novo DNA synthesis during the S-phase of the cell cycle. (jenabioscience.com)
Polymer1
The azidated PP can further undergo copper-catalyzed azide-alkyne cycloaddition with alkyne terminated polymer to obtain PP-based graft copolymers. (utexas.edu)
Cycloadditions1
18. Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions. (nih.gov)
Terminal2
A notable variant of the Huisgen 1,3-dipolar cycloaddition is the copper(I) catalyzed variant, no longer a true concerted cycloaddition, in which organic azides and terminal alkynes are united to afford 1,4-regioisomers of 1,2,3-triazoles as sole products (substitution at positions 1' and 4' as shown above). (wikipedia.org)
Current shortcomings are that the terminal alkyne appears to participate in free-radical polymerizations. (wikipedia.org)
With a stopper molecule such as phenyl azide, well-defined phenyl end-groups are obtained. (wikipedia.org)
Moiety1
In this application, the alkyne is found in the ethynyl moiety of EdU, while the azide is coupled to Alexa Fluor 488, Alexa Fluor 647, or Pacific Blue dyes. (selectscience.net)
Biomolecules3
Alkyne-or Azide-functionalized substrates e.g. fixed and permeabilized cells containing metabolically functionalized Alkyne- or Azide-modified biomolecules. (jenabioscience.com)
A general protocol for labeling of fixed and permeabilized cells containing metabolically functionalized Alkyne- or Azide-modified biomolecules is outlined below (see 3. (jenabioscience.com)
MB 660R Alkyne is often a reagent of choice for imaging of low abundance azide-containing biomolecules. (vectorlabs.com)
Selective1
A general, selective, and atom economic metal-catalyzed conversion of primary diols and amines to highly valuable 2,5-unsubstituted pyrroles is catalyzed by a stable manganese complex in the absence of organic solvents. (organic-chemistry.org)
Proteins3
The presence of copper has been a serious problem, often leading to lost and damaged proteins. (umass.edu)
Following copper catalyzed azide-alkyne cycloaddition, the candidate GlcNAc proteins were detected by SDS-polyacrylamide gel electrophoresis and identified by mass spectrometry. (nih.gov)
He and co-recipient Morten Meldal, University of Copenhagen, Denmark, who is not funded by NIH, then independently introduced a copper-catalyzed click that further refined the chemistry and helped popularize it across biology and the material sciences [2,3]. (nih.gov)
Bertozzi was recognized for expanding the use of click chemistry with so-called bioorthogonal chemistry, which is a copper-free version of the approach that can be used inside living cells without the risk of metal-associated toxicities [4,5]. (nih.gov)
Meldal2
The copper(I)-catalyzed variant was first reported in 2002 in independent publications by Morten Meldal at the Carlsberg Laboratory in Denmark and Valery Fokin and K. Barry Sharpless at the Scripps Research Institute. (wikipedia.org)
Shortly afterward, Meldal and Sharpless (independently of each other) presented the copper catalyzed azide-alkyne cycloaddition. (genengnews.com)
Reagent2
Picolyl)-Azide or Alkyne detection reagent and appropriate solvent (e.g. (jenabioscience.com)
Different copper sources, reduction reagents and Cu(I) stabilizing ligands are available however, for most bioconjugation applications the combination of the Cu(II) salt CuSO 4 as copper source, a water-soluble Cu(I) stabilizing ligand such as BTTAA and sodium ascorbate as a reduction reagent is recommended. (jenabioscience.com)
Dyes1
introduce a fluorescent group for subsequent microscopic imaging (via Alkynes of fluorescent dyes or DBCO-functionalized fluorescent dyes, respectivly). (jenabioscience.com)
Heterogeneous copper catalyst for the cycloaddition of azides and alkynes without additives under ambient conditions. (nih.gov)
For the copper-catalyzed azide-alkyne cycloaddition, stainless steel or copper jet feeds were effective reservoirs of active copper catalyst. (rsc.org)
N -Sulfonyl- and N -acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines followed by in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. (organic-chemistry.org)
Functionalities1
20. clickECM: Development of a cell-derived extracellular matrix with azide functionalities. (nih.gov)
Oxidation1
Using a similar strategy poly(ethylene glycol-co-glycolic acid) can be prepared by the ruthenium-catalyzed oxidation of poly(ethylene glycol) (PEG). (utexas.edu)
Banert1
NH-1,2,3-triazoles are also prepared from alkynes in a sequence called the Banert cascade. (wikipedia.org)
Subsequent1
The route starts with two subsequent Pd-catalyzed monoallylations of amines with allylic alcohols. (organic-chemistry.org)
Complexes1
Our article describing dicopper complexes in the copper-catalyzed azide-alkyne cycloaddition is featured in LBNL's Today at Berkeley Lab (4/17/2017). (micahsziegler.com)
Versatile1
It is expected that the ability to incorporate versatile functional groups, such as azides, into common polyolefin feedstocks should expand their applications and potentially enable the realization of new classes of materials. (utexas.edu)
Sodium1
For lyophilized antibodies, we recommend reconstituting the antibody with glycerol and antimicrobial preservative like sodium azide for the longest shelf life (note that sodium azide is not compatible with HRP-conjugates). (biotium.com)
Ruthenium1
In this dissertation, it is first demonstrated that poly(vinyl ester)s and poly(vinyl ether-co-vinyl ester) can be readily prepared via a ruthenium catalyzed C-H oxyfunctionalization of the corresponding poly(vinyl ether)s under mild conditions. (utexas.edu)
Chemistry3
Despite the importance of azides in synthetic organic chemistry, it is not always easy to synthesize azides owing to the electrophilic nature of azido groups which are susceptible to various nucleophiles, such as carbanions ( Tanimoto and Kakiuchi, 2013 ). (frontiersin.org)
I want to get the latest chemistry news from C&EN in my inbox every week. (acs.org)
C&EN contributor Mark Peplow also joins the Stereo Chemistry crew to talk about his conversation with Nobel Laureate Carolyn Bertozzi. (acs.org)
Modification2
7. Modification of Protein Scaffolds via Copper-Catalyzed Azide-Alkyne Cycloaddition. (nih.gov)
11. Copper-Free Azide-Alkyne Cycloaddition for Peptide Modification of Alginate Hydrogels. (nih.gov)
Formation1
Regioselective formation of 2,5-disubstituted oxazoles via copper(I)-catalyzed cycloaddition of acyl azides and 1-alkynes. (nih.gov)
Group1
BSA contains a thiol group at Cys-34 which is functionalized with an alkyne group. (wikipedia.org)
Surface2
The copper-mediated azide-alkyne cycloaddition is receiving widespread use in material and surface sciences. (wikipedia.org)
Poly(propargyl acrylate) (PA) particles were surface modified through the copper-catalyzed azide/alkyne cycloaddition of azide-terminated indocyanine green (azICG), a near-infrared emitter, and poly(ethylene glycol) (azPEG) chains of various molecular weights. (nih.gov)
Water2
Running the metal-free azide-alkyne cycloaddition in this reactor revealed a dramatic enhancement of the "on water" effect. (rsc.org)
Gold-catalyzed cyclizations of diols and triols to the corresponding hetero- or spirocycles take place in an aqueous medium within nanomicelles, where the hydrophobic effect is operating, thereby driving the dehydrations, notwithstanding the surrounding water. (organic-chemistry.org)