909580

Sigma-Aldrich

TIPS-5-Ethynyl-dU-CEP

Synonym(s):
TIPS-5-Ethynyl dU phosphoramidite, TIPS-5-EdU CEP, TIPS-5-Ethynyl dU CEP
Empirical Formula (Hill Notation):
C50H67N4O8PSi
Molecular Weight:
911.15

form

powder

reaction suitability

reaction type: click chemistry

mp

>300 °C

storage temp.

−20°C

Application

This functional phosphoramidite is used to introduce click handles universally (5′ internal and 3′ end) into oligonucleotides under standard conditions for solid phase synthesis. Afterwards the oligonucleotide (RNA, PNA, DNA) can be efficiently conjugated using a copper catalyzed click reaction to azide functionalized moieties such as fluorescent dye azides and azido amino acids. In contrast to 5-Ethynyl dU CEP, TIPS-5-EdU CEP allows side product free synthesis of highly modified oligonucleotides (>10 modifications).

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Sachin A Ingale et al.
The Journal of organic chemistry, 78(22), 11271-11282 (2013-10-22)
Clickable oligonucleotides with ethynyl residues in the 5-position of pyrimidines ((eth)dC and (eth)dU) or the 7-position of 7-deazaguanine ((eth)c(7)G(d)) are hydrated during solid-phase oligonucleotide synthesis and workup conditions. The side products were identified as acetyl derivatives by MALDI-TOF mass spectra...
Johannes Gierlich et al.
Organic letters, 8(17), 3639-3642 (2006-08-11)
[reaction: see text] We report the development of the Cu(I)-catalyzed Huisgen cycloaddition (click) reaction for the multiple postsynthetic labeling of alkyne-modified DNA. A series of alkyne-modified oligodeoxyribonucleotides (ODNs) of increasing alkyne density were prepared, and the click reaction using various...

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