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Review
. 2009 Sep;109(9):4207-20.
doi: 10.1021/cr9001462.

Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry

Franck Amblard  1 , Jong Hyun Cho, Raymond F Schinazi
Affiliations
Review

Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry

Franck Amblard et al. Chem Rev. 2009 Sep.
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Nucleoside Analogs Used for the Treatment of HIV, HBV, HCV, HSV, CMV and VZV.
Figure 2
Figure 2
Nucleoside Analogs Used for the Treatment of Various Cancers.
Figure 3
Figure 3
Actives Five Membered Heterocyclic Based Nucleosides Analogs.
Figure 4
Figure 4
Adenosine Dimer 24.
Figure 5
Figure 5
Structures of Compounds 37–42.
Figure 6
Figure 6
Rational for the Design of Compound 47.
Figure 7
Figure 7
Chemical Structure of Boronic Acid-Labeled Thymidine-5’-Triphosphate 52.
Figure 8
Figure 8
Structure of Nucleosides Conjugates 53–56.
Figure 9
Figure 9
Structure of Nucleosides Conjugates 57–59.
Figure 10
Figure 10
Structure of Nucleosides Conjugates 60–62.
Figure 11
Figure 11
Structure of 1,2,3-Triazole-Fused Oligonucleosides Analogs 63–66.
Figure 12
Figure 12
Structure of Pleuromutilin 69 and Pleuromutilin Bioconjugates 70.
Figure 13
Figure 13
Structure of Adenosine-Quaterthiophene 81 and Corresponding Thymidine 80.
Figure 14
Figure 14
AFM tapping-mode image of a 1:1 mixture of adenosine-quaterthiophene 81 and corresponding thymidine 80 deposited from toluene on HOPG after annealing: topography representation (17 × 17 µm2) (left) and detailed amplitude image (2.5 × 2.5 mm2) (right). In the middle a calculated model for the fiber growth (gray arrow) is shown, including a detail of the molecular interactions involved (oval and square insets) and the molecular dimensions. Reprinted with permission from ref 35. Copyright 2008 American Chemical Society.
Figure 15
Figure 15
Structures of oligonucleotides analogs 84–86
Scheme 1
Scheme 1
1,3-Dipolar Cycloaddition Between Azides and Alkynes
Scheme 2
Scheme 2
Most Common Methods for the Introduction of a Terminal Alkyne
Scheme 3
Scheme 3
Most Common Methods for the Introduction of an Azide Functional Group
Scheme 4
Scheme 4
Synthesis of 1,2,3-Triazolo Nucleosides Analogs 3.
Scheme 5
Scheme 5
Synthesis of 1,2,3-Triazolo Nucleosides Analogs 5.
Scheme 6
Scheme 6
Synthesis of 1,2,3-Triazolo Nucleosides Analogs 7 Using Microwave Irradiation.
Scheme 7
Scheme 7
Synthesis of 1,2,3-Triazolo Nucleosides Analogs 3C Using Microwave Irradiation.
Scheme 8
Scheme 8
Synthesis of Nucleobase-Simplified cADPR Mimics 11.
Scheme 9
Scheme 9
Plausible Mechanism of Preparation of Compound 15.
Scheme 10
Scheme 10
Synthesis of Bis-triazolyl Nucleosides 17.
Scheme 11
Scheme 11
Reactivity of Azido Compound 18 Under CuAAC Conditions.
Scheme 12
Scheme 12
Plausible Mechanism for the Formation of Amide 21A.
Scheme 13
Scheme 13
Synthesis of 2-(1,2,3-Triazolyl)Adenosine Derivatives 27 and 29.
Scheme 14
Scheme 14
Azido/Tetrazole Tautomerism of 2-Substituted Adenosine Derivative 28.
Scheme 15
Scheme 15
Double Effect of the Sonogashira Conditions on Compound 31.
Scheme 16
Scheme 16
Synthesis of 2-Triazole Substituted 36, Analogs of Sal-AMS 33.
Scheme 17
Scheme 17
Synthesis of 6’-Branched Locked Nucleic Acid 45.
Scheme 18
Scheme 18
Solid-Phase Synthesis of Heterocyclic Nucleosides Analogs 51.
Scheme 19
Scheme 19
Synthesis of Compound 68.
Scheme 20
Scheme 20
Triazole Synthesis in Microliter Plate for Screening in situ.
Scheme 21
Scheme 21
Synthesis of Compounds 78 and 79.
Scheme 22
Scheme 22
One-pot Synthesis of Radiolabeled Conjugate 83.
Scheme 23
Scheme 23
Synthesis of 10-Mer TLDNA 90.
Scheme 24
Scheme 24
Azido Resin Derivatization with a Nucleoside Monomer using CuAAC.
Scheme 25
Scheme 25
Postsynthetic and Presynthetic Strategies for DNA Labeling.
Scheme 26
Scheme 26
Synthesis of Lipid-Oligonucleotides Conjugates 97.
Scheme 27
Scheme 27
Synthesis of Modified Oligonucleotides 100.
Scheme 28
Scheme 28
Synthesis of “Fleximers” 102.
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References

    1. Huisgen R, Szeimies G, Möbius L. Chem.Ber. 1967;100:2494.

    1. For reviews see: Kolb HC, Sharpless KB. Drug Discovery Today. 2003;8:1128. Bock VD, Hiemstra H, van Maarseveen JH. Eur. J. Org. Chem. 2006;51 Binder WH, Kluger C. Curr. Org. Chem. 2006;10:1791. Binder WH, Sachsenhofer R. Macromol. Rapid Commun. 2007;28:15. Moorhouse AD, Moses JE. Chem. Med. Chem. 2008;3:715. Binder WH, Sachsenhofer R. Macromol. Rapid Commun. 2008;29:952. Lutz J-F, Zarafshani Z. Adv.Drug. Deliv. Rev. 2008;60:958.

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    1. For Pd-catalyzed Sonogashira reaction on nucleosides see: Agrofoglio LA, Gillaizeau I, Saito Y. Chem. Rev. 2003;103:1875. For the preparation of alkynes from aldehydes: Roth GJ, Liepold B, Mömlller SG, Bestmann HJ. Synthesis. 2004;59 For a review on the preparation of azidonucleosides see: Pathak T. Chem. Rev. 2002;102:1623.

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