• Home
  • Search Results
  • Postsynthetic conjugation of RNA to carboxylate and dicarboxylate molecules.

Postsynthetic conjugation of RNA to carboxylate and dicarboxylate molecules.

Nucleosides, nucleotides & nucleic acids (2015-10-01)
Yossi Shemesh, Eylon Yavin
ABSTRACT

Carboxylates and dicarboxylates are important phosphate mimics. Herein, we present a simple synthetic route for the preparation of RNA carboxylate/dicarboxylate conjugates, starting from suitably protected NH2- and COOH-containing molecules that are coupled to the RNA on the solid support. The key point in our method was the use of trimethylsilylethanol (TMSE-OH) protecting group, which is removed simultaneously with the silyl protecting group on the 2'-OH of the RNA ribose (e.g. t-Butyldimethylsilyl) during the final RNA cleavage/deprotection steps. The usefulness of this method was demonstrated by preparing different RNA-phosphate mimics oligos.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Hydrochloric acid, ACS reagent, 37%
Sigma-Aldrich
Hydrochloric acid, ACS reagent, 37%
Sigma-Aldrich
N,N-Diisopropylethylamine, ReagentPlus®, ≥99%
Sigma-Aldrich
Hydrogen chloride solution, 4.0 M in dioxane
Sigma-Aldrich
Hydrochloric acid solution, 1.0 N, BioReagent, suitable for cell culture
Sigma-Aldrich
Hydrochloric acid, 36.5-38.0%, BioReagent, for molecular biology
Sigma-Aldrich
Ammonia solution, 7 N in methanol
Sigma-Aldrich
1-Butanol, anhydrous, 99.8%
Sigma-Aldrich
Hydrochloric acid, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., fuming, ≥37%, APHA: ≤10
Sigma-Aldrich
N,N-Diisopropylethylamine, purified by redistillation, 99.5%
Sigma-Aldrich
1-Butanol, 99.9%
Sigma-Aldrich
CDI, reagent grade
Sigma-Aldrich
1-Butanol, ACS reagent, ≥99.4%
Sigma-Aldrich
Ammonia, anhydrous, ≥99.98%
Supelco
Hydrochloric acid solution, volumetric, 0.1 M HCl (0.1N), endotoxin free
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, meets USP testing specifications
Sigma-Aldrich
Hydrogen chloride solution, 2.0 M in diethyl ether
Sigma-Aldrich
Methylamine solution, 2.0 M in THF
Sigma-Aldrich
1-Butanol, for molecular biology, ≥99%
Sigma-Aldrich
Palladium hydroxide on carbon, extent of labeling: 20 wt. % loading (dry basis), matrix carbon, wet support
Sigma-Aldrich
Hydrochloric acid, meets analytical specification of Ph. Eur., BP, NF, fuming, 36.5-38%
Sigma-Aldrich
CDI, ≥97.0% (T)
Sigma-Aldrich
Butyl alcohol, natural, ≥99.5%, FCC, FG
Sigma-Aldrich
N,N-Diisopropylethylamine, 99.5%, biotech. grade
Sigma-Aldrich
Methylamine solution, 2.0 M in methanol
Sigma-Aldrich
Hydrochloric acid solution, ~6 M in H2O, for amino acid analysis
Sigma-Aldrich
Ammonia solution, 0.4 M in THF
Sigma-Aldrich
Hydrogen chloride solution, 3 M in cyclopentyl methyl ether (CPME)
Sigma-Aldrich
Hydrochloric acid solution, 32 wt. % in H2O, FCC
Sigma-Aldrich
Hydrogen chloride solution, 1.0 M in diethyl ether