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TIPS-5-Ethynyl-dU-CE Phosphoramidite

Clickable phosphoramidite for Oligo synthesis

Currency:  
  • Size
  • Catalog No.
  • Price
  • 100 mg
  • BCA-25-100

  • € 250,00
  • 250 mg
  • BCA-25-250

  • € 580,00
  • 1 g
  • BCA-25-1g

  • € 1.800,00
Clear
  • TIPS-5-Ethynyl-dU-CE Phosphoramidite can be used instead of the 5-Ethynyl-dU-CE Phosphoramidite under standard conditions for solid phase synthesis. The protecting group reduces the risk of side products. The oligo is deprotected after the synthesis leading to ethynyl modified oligonucleotides. The usage of TIPS-5-Ethynyl-dU-CEP in combination with other alkyne modified phosphoramidites (e.g. 5-Ethynyl-dU-CEP or C8-Alkyne-dU-CEP) enables the possibility to create Oligos which can be modified by Click Chemistry consecutively. Therefore, firstly the unprotected alkyne is clicked and after deprotection of TIPS the second click can be performed.

     

    LITERATURE

    Ethynyl Side Chain Hydration during Synthesis and Workup of “Clickable” Oligonucleotides: Bypassing Acetyl Group Formation by Triisopropylsilyl Protection, S. A. Ingale et al., 2013J. Org. Chem., Vol. 78, p. 11271–11282.

    https://doi.org/10.1021/jo401780u

    Nucleosides And Oligonucleotides With Diynyl Side Chains: The Huisgen-Sharpless Cycloaddition “Click Reaction” Performed On Dna And Their Constituents, F. Seela et al., 2007Nucleosides, Nucleotides & Nucleic Acids, Vol. 26, p. 597–601.

    https://doi.org/10.1080/15257770701490308

    Postsynthetic DNA Modification through the Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction, P. M. E. Gramlich et al., 2008Angew. Chemie Int. Ed., Vol. 47, p. 8350–8358.

    https://doi.org/10.1002/anie.200802077

    Efficiency and Fidelity in a Click-Chemistry Route to Triazole Dendrimers by the Copper(I)-Catalyzed Ligation of Azides and Alkynes, P. Wu et al., 2004, Angew. Chemie Int. Ed., Vol. 43, p. 3928–3932.

    https://doi.org/10.1002/anie.200454078

    Peptidotriazoles on Solid Phase:  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides, C. W. Tornøe et al., 2002, J. Org. Chem., Vol. 67, p. 3057–3064.

    https://doi.org/10.1021/jo011148j

    Click Chemistry: Diverse Chemical Function from a Few Good Reactions, H. C. Kolb et al., 2001, Angew. Chemie Int. Ed., Vol. 40, p. 2004–2021.

    https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5

    • Molecular Formula

      C50H67N4O8PSi

    • Shelf Life

      12 months unopened after receipt

    • Storage Conditions

      -20 °C dry, inert gas

    • Molecular Weight

      911.16 g/mol

    • Purity

      ≥ 90% (LCMS and 31P NMR)

    • Physical State

      off-white colored fluffy solid

    • CAS Number

      1472616-97-9

    • Additional name

      5-TIPS-EDU Amidite; TIPS-5-Ethynyl dU CEP; TIPS-5-Ethynyl dU Phosphoramidite

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