1,3‐Dipolar Cycloadditions. Past and Future

Huisgen, Rolf

doi:10.1002/anie.196305651

Cited by 2,772 publications

(1,278 citation statements)

References 197 publications

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“…In the last years triazolium derivatives have attracted the attention of scientists because the N-alkyl-1,2,3-triazoles moiety is easily accessible through the versatile copper-catalyzed (CuAAC) [2 + 3] cycloaddition (Huisgen, 1963;Meldal and Tornoe 2008;Finn and Fokin, 2010).…”

Section: Introductionmentioning

confidence: 99%

Development and characterization of co-loaded curcumin/triazole-halloysite systems and evaluation of their potential anticancer activity

Riela

Massaro

Colletti

et al. 2014

International Journal of Pharmaceutics

109

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Section: Introductionmentioning

confidence: 99%

Development and characterization of co-loaded curcumin/triazole-halloysite systems and evaluation of their potential anticancer activity

Riela

Massaro

Colletti

et al. 2014

International Journal of Pharmaceutics

109

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“…The dipolarophile can be almost any double or triple bond, containing functionality such as C≡C, 48 C=C, 49 C≡N, 50 C=N, 51 C=O, 5 and C=S. 52 The -bond may be isolated, conjugated 53 or part of a cumulene 54 system.…”

Section: The Dipolarophilementioning

confidence: 99%

“…A synchronous, concerted mechanism was proposed by Huisgen,5,56,57 whereas the stepwise, diradical pathway was favoured by Firestone (Scheme 4). [58][59][60] …”

Section: Mechanism Of 13-dipolar Cycloadditionmentioning

confidence: 99%

“…The nitrile oxide is generated very slowly so that a low stationary concentration is maintained. 5 The 1,3-dipolar cycloaddition of nitrile oxides is a very versatile reaction for the construction of stereoselective compounds. The isoxazoline ring can be readily cleaved, allowing stereocontrolled access to a variety of acyclic compounds, including -hydroxyketones and -amino alcohols (Scheme 14).…”

Section: Scheme 13mentioning

confidence: 99%

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Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references)

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“…1,2 Recently, two reactions based on the specific reactivity of the azide moiety were introduced. [3][4][5] One method is based on the [3 + 2] cyclo addition reaction of an azide and a terminal alkyne 6 promoted by copper catalysis. 7,8 This reaction has been employed extensively and recently been extended for conjugation of DNA.…”

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confidence: 99%

A nucleoside triphosphate for site-specific labelling of DNA by the Staudinger ligation

Weisbrod

Marx

2007

Chem. Commun.

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A novel nucleotide building block for enzymatic synthesis of azide modified DNA and subsequent conjugation via Staudinger ligation was developed.Many studies of complex biological systems are only feasible through conjugation of biopolymers with other functional molecules like dyes or affinity tags. Linkage of a complex biomolecule with another molecular entity is often a challenging task. Albeit several bioconjugation methods are available, truly chemoselective methods are rarely represented. 1,2 Recently, two reactions based on the specific reactivity of the azide moiety were introduced. [3][4][5] One method is based on the [3 + 2] cyclo addition reaction of an azide and a terminal alkyne 6 promoted by copper catalysis. 7,8 This reaction has been employed extensively and recently been extended for conjugation of DNA. 9,10 On the other side, the so-called Staudinger ligation developed by Bertozzi [11][12][13] readily occurs between an azide and a phosphine to form an azaylide that can be trapped by an acyl group to form a stable amide bond. This reaction has been employed in numerous applications e.g. for the conjugation of carbohydrates, protein 14,15 and phage particles 16 as well as peptide ligation and immobilization. [17][18][19][20][21] Recently, methods were devised to employ the Staudinger ligation for conjugation of DNA. It was shown that conjugation of an azide functionality via a suitable linker system enables conjugation of dyes to the 59-end of single stranded DNA. 22 Rajski et al. employed the Staudinger ligation to conjugate DNA with phenanthroline moieties for subsequent Cu(I) induced strand scission. 23 Here we report on the development of a novel azide modified nucleoside triphosphate building block, that is readily incorporated into DNA enzymatically by a DNA polymerase. The resulting double stranded azide modified DNA can be smoothly conjugated with modified phosphines via the Staudinger ligation.Our strategy to modify DNA site-specifically with azide functions by use of DNA polymerases for subsequent Staudinger ligation is depicted in Scheme 1B. The first step consists of a DNA polymerase reaction in which one of the natural nucleoside triphosphates (dNTPs) is substituted by a modified analogue that contains an azide functionality. Obviously the success of this step is contingent on the ability of a DNA polymerase to accept the modified nucleotide. The azide-modified double stranded DNA in turn should serve as substrate for Staudinger ligation with a suitably functionalized phosphine.Thus, first we developed the synthesis of the nucleoside triphosphate 1, a 29-deoxyadenosine analogue (Scheme 1A). Since it has been shown that 7-modified 7-deaza-29-deoxyadenosine derivatives are accepted by DNA polymerases 24-28 we focused our synthesis on these kinds of analogues. Following a published procedure 24 we synthesised a 7-deaza-29-deoxyadenosine 2, which was readily converted into the corresponding triphosphate 3. After saponification 24 the azide moiety was introduced via EDC promoted amide bond...

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1,3‐Dipolar Cycloadditions. Past and Future

Cited by 2,772 publications

References 197 publications

Development and characterization of co-loaded curcumin/triazole-halloysite systems and evaluation of their potential anticancer activity

Development and characterization of co-loaded curcumin/triazole-halloysite systems and evaluation of their potential anticancer activity

Asymmetric 1,3-dipolar cycloadditions of acrylamides

A nucleoside triphosphate for site-specific labelling of DNA by the Staudinger ligation

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