TIPS-5-Ethynyl-dU-CE Phosphoramidite
Clickable phosphoramidite for Oligo synthesis
| 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 |
Chemical Properties
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Molecular Formula
C50H67N4O8PSi
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Shelf Life
12 months unopened after receipt
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Storage Conditions
-20 °C dry, inert gas
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Molecular Weight
911.16 g/mol
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Purity
≥ 95% (HPLC and 31P NMR)
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Physical State
off-white colored fluffy solid
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CAS Number
1472616-97-9
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Additional name
5-TIPS-EDU Amidite; TIPS-5-Ethynyl dU CEP; TIPS-5-Ethynyl dU Phosphoramidite
Product Information
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., 2013, J. 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., 2007, Nucleosides, 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., 2008, Angew. 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