5-Ethynyl-dU-CE Phosphoramidite
Clickable phosphoramidite for Oligo synthesis
| Size | Catalog No. | Price |
|---|---|---|
| 250 mg | BCA-09-250 | € 320,00 |
| 1 g | BCA-09-1g | € 1.050,00 |
Chemical Properties
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Molecular Formula
C41H47N4O8P
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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
754.81 g/mol
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Purity
≥ 95% (HPLC & 31P-NMR)
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Physical State
white to light brown solid
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CAS Number
615288-66-9
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Additional name
5-Ethynyl-dU CEP; 2′-Deoxy-5′-DMT-5-ethynyluridine 3′-CE phosphoramidite; 5′-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3′-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2′-deoxy-5-ethynyluridine; 5′-O-[Bis(4-methoxyphenyl)phenylmethyl]-2′-deoxy-5-ethynyl-uridine 3′-[2-cyanoethyl bis(1-methylethyl)phosphoramidite]
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Preparation/Handling
This phosphoramidite is used under standard conditions for solid phase synthesis of oligonucleotides.
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Solubility
MeCN
Product Information
5-Ethynyl-dU-CE Phosphoramidite is an universal alkyne modifier that can be used under standard conditions for solid phase synthesis of oligonucleotides. It has shown to be incorporated into DNA oligomers with high coupling efficiency.
LITERATURE
DNA duplexes stabilized by modified monomer residues: synthesis and stability, D. Graham et al., 1998, J. Chem. Soc., Perkin Trans. 1, p. 1131–1138.
https://doi.org/10.1039/A707031D
A Versatile Modification of On-Column Oligodeoxynucleotides Using a Copper-Catalyzed Oxidative Acetylenic Coupling Reaction, N. Minakawa et al., 2003, J. Am. Chem. Soc., Vol. 125, p. 11545–11552.
https://doi.org/10.1021/ja036055t
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
Click Reaction on Solid Phase Enables High Fidelity Synthesis of Nucleobase-Modified DNA, F. Tolle et al., 2016, Bioconjugate Chem., Vol. 27, p. 500–503.
https://doi.org/10.1021/acs.bioconjchem.5b00668
Efficient Long-Range Hole Transport Through G-Quadruplexes, J. Wu et al., 2017, Chemistry – A European Journal, Vol. 23(56), p. 13980-13985.
https://doi.org/10.1002/chem.201702478
Pyrene-Modified DNA Aptamers with High Affinity to Wild-Type EGFR and EGFRvIII, E. Zavyalova et al., 2020, Nucleic Acid Therapeutics, Vol. 30(3), p. 175-187.