共查询到20条相似文献,搜索用时 0 毫秒
1.
Wang Q Chan TR Hilgraf R Fokin VV Sharpless KB Finn MG 《Journal of the American Chemical Society》2003,125(11):3192-3193
The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand. The process has been employed to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties. The chelating ligand plays a crucial role in stabilizing the Cu(I) oxidation state and protecting the protein from Cu(triazole)-induced denaturation. Because the azide and alkyne groups themselves are unreactive with protein residues or other biomolecules, their ligation is of potential utility as a general bioconjugation method. 相似文献
2.
Cavalli S Tipton AR Overhand M Kros A 《Chemical communications (Cambridge, England)》2006,(30):3193-3195
A generic method for the efficient in-situ modification of liposomes is described based on "click" chemistry, and a simple colorimetric assay is developed for monitoring the reaction. 相似文献
3.
《Tetrahedron letters》1986,27(35):4137-4140
4.
Toward the goal of assigning function to the tens of thousands of protein products encoded by eukaryotic and prokaryotic genomes, the field of proteomics requires new technologies that can functionally characterize proteins within the dynamic environment of the cell, where these biomolecules are subject to myriad posttranslational modifications and the actions of endogenous activators and inhibitors. Here, we report an advanced strategy for activity-based protein profiling (ABPP) that addresses this important need. We show that several enzymes can be labeled in an activity-based manner both in vitro and in vivo by an azido-sulfonate ester probe and that these labeling events can be detected in whole proteomes by copper-catalyzed ligation with a rhodamine-alkyne reagent. This click chemistry-based strategy for ABPP represents a unique and versatile method for functional proteome analysis. 相似文献
5.
Szychowski J Mahdavi A Hodas JJ Bagert JD Ngo JT Landgraf P Dieterich DC Schuman EM Tirrell DA 《Journal of the American Chemical Society》2010,132(51):18351-18360
The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na(2)S(2)O(4), 2% HOCH(2)CH(2)SH, 10% HCO(2)H, 95% CF(3)CO(2)H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO(2)H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies. 相似文献
6.
Crina M. Orac 《Tetrahedron letters》2009,50(12):1261-3485
A new and a direct synthetic method for the construction of the bicyclo[3.2.1]octane system is envisioned by assembling cyclic allylsilanes with electron-deficient double bonds in a single step via a formal diastereoselective Lewis acid-promoted [3+2] cycloaddition. 相似文献
7.
The review, covering the literature of roughly the last three decades, describes the [3+2] cycloaddition reactions of metalla dipolarophiles M=X with organic 1,3-dipoles, and of metalla 1,3-dipoles, M---X=Y and X---M=Y, with organic dipolarophiles. The resulting 5-membered metalla heterocycles can undergo consecutive insertion and/or reductive elimination reactions to give synthetically interesting organic heterocycles. The reactivity of the organometal 1,3-dipoles is explained by extensive series of isolobal transformations to classic organic 1,3-dipoles. 相似文献
8.
Yoshiro Masuyama Kazuki YoshikawaNoriyuki Suzuki Kenji HaraAtsushi Fukuoka 《Tetrahedron letters》2011,52(51):6916-6918
Copper(II)-exchanged hydroxyapatite, prepared by ion-exchanging of Ca(II) in calcium hydroxyapatite [Ca10(PO4)6(OH)2] with Cu(NO3)2 at 70 °C in water, functions as a reusable heterogeneous catalyst with neither reducing agents nor bases for azide-alkyne [3+2] cycloaddition at 50 °C in water under air. 相似文献
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10.
The synthesis of a phosphoramidite reagent for 5′-modification of oligonucleotides by introducing an arylacetylene residue
has been described. Using the reaction with 3-(perylen-3-yl)propyl azide as an example, it was shown that the acetylene derivatives
of oligonucleotides synthesized using this reagent undergo CuI-catalyzed [3+2] dipolar cycloaddition. Fluorescent conjugates were obtained in high yields and characterized by mass spectra.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1220–1226, July, 2006. 相似文献
11.
Trost BM Stambuli JP Silverman SM Schwörer U 《Journal of the American Chemical Society》2006,128(41):13328-13329
Transition-metal-catalyzed trimethylenemethane (TMM) [3 + 2] cycloadditions provide direct routes to functionalized cyclopentanes. This reaction has been shown to be a highly chemo-, regio-, and diastereoselective process. We report a palladium-catalyzed asymmetric [3 + 2] trimethylenemethane (TMM) cycloaddition between 3-acetoxy-2-trimethylsilylmethyl-1-propene and various di- and trisubstituted olefins. Yields of exo-methylenecyclopentane products range from 59 to 99%, and enantiomeric excesses range from 58 to 92% ee. 相似文献
12.
Cyclic ketimines as electrophiles for [2+2] and [3+2] cycloaddition reactions of allenoates have been developed, affording functionalized sultam-fused azetidines and dihydropyrroles, respectively, in good yields with high regioselectivities. 相似文献
13.
Strain-promoted cycloadditions of cyclic nitrones with biaryl-aza-cyclooctynone (BARAC) proceed with rate constants up to 47.3 M(-1) s(-1), this corresponds to a 47-fold rate enhancement relative to reaction of BARAC with benzyl azide and a 14-fold enhancement over previously reported strain promoted alkyne-nitrone cycloadditions (SPANC). Studies of the SPANC reaction using the linear free energy relationship defined by the Hammett equation demonstrated that the cycloaddition reaction has a rho value of 0.25 ± 0.04, indicating that reaction is not sensitive to substituents and thus should have broad applicability. 相似文献
14.
《Tetrahedron letters》1986,27(17):1913-1914
Pyrolysis of N-allyl enaminoesters is a general method for the stereoselective synthesis of 3-azabicyclo[3.2.0] heptenones ; the reaction involves a [2+2] intramolecular cycloaddition of an intermediate iminoketene. 相似文献
15.
Irradiation of 2-cyanochromone in the presence of olefins gave rise to [3 + 2] cycloadducts together with the formation of normal [2 + 2] cycloadducts with the product ratio being temperature-dependent. The mechanism involving a vinyl nitrene intermediate was proposed. 相似文献
16.
The [2+2+2] cycloaddition is an elegant, atom-efficient and group tolerant process for the synthesis of carbo- and heterocycles, mostly aromatic, involving the formation of several C-C bonds in a single step. Cyclotrimerisation is catalyzed by a variety of organometallic complexes, including more than 15 different metals. The aim of this tutorial review is to point out the most recent advances in this field and to encourage the use of this reaction enroute to complex molecules. After summarizing the most common catalysts and reaction conditions generally used, we survey the mechanistic features currently accepted for this reaction. Section 4 covers the scope of the different [2+2+2] cycloaddition versions starting with the cyclotrimerisation of three triple bonds, including nitriles, with especial emphasis on asymmetric reactions that create central, axial or planar chirality. Then, reactions that use double bonds are addressed. Finally, the most outstanding examples of natural products synthesis using [2+2+2] cycloadditions as a key step reported recently are shown. 相似文献
17.
Enantioselective cycloaddition using chiral transition metal catalysts is an atom-economical and efficient synthetic tool for the construction of chiral carbo- and heterocyclic skeletons. This short account discloses our recent results of inter- and intramolecular enantioselective [2 + 2 + 2] cycloadditions of alkyne and/or alkene moiety(ies). Chiral iridium complexes catalyzed the alkyne trimerization for the generation of axial chirality(ies), and chiral rhodium ones catalyzed alkyne-alkyne-alkene cyclization for the generation of a quaternary carbon including spirocyclic system. 相似文献
18.
An efficient, modular synthesis of triptycene derivatives is presented, in which the triptycene ring system is constructed from readily available anthraquinone and alkyne starting materials. A rhodium-catalyzed alkyne cyclotrimerization reaction serves as the key step in this new method for the preparation of these useful unnatural products. 相似文献
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20.
Surface modification of magnetic nanoparticle via Cu(I)-catalyzed alkyne-azide [2 + 3] cycloaddition 总被引:1,自引:0,他引:1
The Cu(I)-catalyzed alkyne-azide [2 + 3] cycloaddition has been demonstrated to be an effective and orthogonal conjugation reaction to covalently immobilize biomolecules on magnetic nanoparticles (MNPs). The azido group on the MNP surface provides better conjugation efficiency with alkynated molecules. Moreover, the C-terminal alkynated protein was site-specifically immobilized on MNP. The protein binding activity presented by site-specific immobilization is higher than that by random amide bond formation. 相似文献