Synthesis of the oligoribonucleotides incorporating 8-oxo-guanosine and evaluation of their base pairing properties

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Abstract

6-O-7-N-Bis(diphenylcarbamoyl)-2-N-phenoxyacetyl-5'-O-dimethoxytrityl-2'-O- {[(triisopropyl- silyl)oxy]methyl}-8-oxoguanosine-3'-yl-β-cyanoethyl-N,N- diisopropylphosphoramidite (5) was synt- hesized as a new phosphoramidite precursor unit for the synthesis of RNA. Compound 5 was successfully incorporated into the middle of the RNA sequences, and the synthesized RNAs were identified by MALDI-TOF mass measurements. Their properties were evaluated for formation of the RNA duplex and RNA/DNA heteroduplex. ORNs 1 and 4 containing 8-oxo-G can form base pairs with rC or dC in an anti conformation, while it can also interact with rA or dA in a syn conformation in the RNA duplex or RNA/DNA heteroduplex. The described synthetic method is therefore a useful procedure for the synthesis of ORN containing 8-oxo-G and contributes to the study of 8-oxo-G in RNA.

Original languageEnglish
Pages (from-to)124-136
Number of pages13
JournalNucleosides, Nucleotides and Nucleic Acids
Volume32
Issue number3
DOIs
Publication statusPublished - Jan 1 2013

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Oligoribonucleotides
Guanosine
Base Pairing
RNA
Nucleic Acid Heteroduplexes
Nucleic Acid Conformation
Conformations
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry

All Science Journal Classification (ASJC) codes

  • Genetics
  • Biochemistry
  • Molecular Medicine

Cite this

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title = "Synthesis of the oligoribonucleotides incorporating 8-oxo-guanosine and evaluation of their base pairing properties",
abstract = "6-O-7-N-Bis(diphenylcarbamoyl)-2-N-phenoxyacetyl-5'-O-dimethoxytrityl-2'-O- {[(triisopropyl- silyl)oxy]methyl}-8-oxoguanosine-3'-yl-β-cyanoethyl-N,N- diisopropylphosphoramidite (5) was synt- hesized as a new phosphoramidite precursor unit for the synthesis of RNA. Compound 5 was successfully incorporated into the middle of the RNA sequences, and the synthesized RNAs were identified by MALDI-TOF mass measurements. Their properties were evaluated for formation of the RNA duplex and RNA/DNA heteroduplex. ORNs 1 and 4 containing 8-oxo-G can form base pairs with rC or dC in an anti conformation, while it can also interact with rA or dA in a syn conformation in the RNA duplex or RNA/DNA heteroduplex. The described synthetic method is therefore a useful procedure for the synthesis of ORN containing 8-oxo-G and contributes to the study of 8-oxo-G in RNA.",
author = "Yohei Koga and Yosuke Taniguchi and Shigeki Sasaki",
year = "2013",
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AU - Koga, Yohei

AU - Taniguchi, Yosuke

AU - Sasaki, Shigeki

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AB - 6-O-7-N-Bis(diphenylcarbamoyl)-2-N-phenoxyacetyl-5'-O-dimethoxytrityl-2'-O- {[(triisopropyl- silyl)oxy]methyl}-8-oxoguanosine-3'-yl-β-cyanoethyl-N,N- diisopropylphosphoramidite (5) was synt- hesized as a new phosphoramidite precursor unit for the synthesis of RNA. Compound 5 was successfully incorporated into the middle of the RNA sequences, and the synthesized RNAs were identified by MALDI-TOF mass measurements. Their properties were evaluated for formation of the RNA duplex and RNA/DNA heteroduplex. ORNs 1 and 4 containing 8-oxo-G can form base pairs with rC or dC in an anti conformation, while it can also interact with rA or dA in a syn conformation in the RNA duplex or RNA/DNA heteroduplex. The described synthetic method is therefore a useful procedure for the synthesis of ORN containing 8-oxo-G and contributes to the study of 8-oxo-G in RNA.

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