TY - JOUR
T1 - Synthesis of the oligoribonucleotides incorporating 8-oxo-guanosine and evaluation of their base pairing properties
AU - Koga, Yohei
AU - Taniguchi, Yosuke
AU - Sasaki, Shigeki
N1 - Funding Information:
Received 1 December 2012; accepted 14 January 2013. This study was supported by a Grant-in-Aid Scientific Research (S) (Grant Numbers 21229002 for Shigeki Sasaki) and for Challenging Exploratory Research (Grant Number 24659047 for Yosuke Taniguchi) from JSPS. Yosuke Taniguchi acknowledges support from a Kyushu University Interdisciplinary Program in Education and Projects in Research Development (P&P). Address correspondence to Shigeki Sasaki, Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka, 812-8582 Japan. E-mail: [email protected]
PY - 2013/1/1
Y1 - 2013/1/1
N2 - 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.
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.
UR - https://www.scopus.com/pages/publications/84875946685
UR - https://www.scopus.com/pages/publications/84875946685#tab=citedBy
U2 - 10.1080/15257770.2013.767461
DO - 10.1080/15257770.2013.767461
M3 - Article
C2 - 23473100
AN - SCOPUS:84875946685
SN - 1525-7770
VL - 32
SP - 124
EP - 136
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
IS - 3
ER -