EFFICIENT ASSESSMENT OF MODIFIED NUCLEOSIDE STABILITY UNDER CONDITIONS OF AUTOMATED OLIGONUCLEOTIDE SYNTHESIS: CHARACTERIZATION OF THE OXIDATION AND OXIDATIVE DESULFURIZATION OF 2-THIOURIDINE

In order to efficiently assess the chemical stability of modified nucleosides to the reagents and conditions of automated oligonucleotide synthesis, we designed, developed and tested a scheme in which the modified nucleoside, directly attached to a solid support, is exposed to the cyclic chemistry o...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2001-12, Vol.20 (10-11), p.1871-1879
Main Author: Sochacka, E.
Format: Article
Language:English
Subjects:
Acetonitriles - chemistry
Carbon Tetrachloride - chemistry
Chromatography, High Pressure Liquid
Hydrogen Peroxide - chemistry
Models, Chemical
Nucleic Acid Denaturation
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Oxygen - metabolism
Sulfur - chemistry
Thiouridine - analogs & derivatives
Thiouridine - chemistry
Time Factors
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Summary:In order to efficiently assess the chemical stability of modified nucleosides to the reagents and conditions of automated oligonucleotide synthesis, we designed, developed and tested a scheme in which the modified nucleoside, directly attached to a solid support, is exposed to the cyclic chemistry of the instrument. Stability of 2-thiouridine against different oxidizers was investigated. Tertbutyl hydroperoxide (1 M) in anhydrous acetonitrile was a more effective oxidizer for the incorporation of 2-thiouridine into oligonucleotide chains than the same oxidizer in methylene chloride. Carbon tetrachloride/water in the presence of a basic catalyst was superior in maintaining the thiocarbonyl function, but its utility for RNA synthesis has yet to be fully tested, whereas 2-phenylsulfonyloxaziridine was a very efficient reagent for oxidative desulfurization of 2-thiouridine.
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-100107198