Synthesis and properties of 2'-O-methyl-2-thiouridine and oligoribonucleotides containing 2'-O-methyl-2-thiouridine.
A new method for the synthesis of 2'-O-methyl-2-thiouridine (s2Um) found in thermophilic bacterial tRNA was developed. Structural properties of s2Um and s2Um(p)U were studied by using 1H NMR spectroscopy. A modified nonaribonucleotide (RNA*: 5'-CGUUs2UmUUGC-3') was synthesized to study the base-recognition ability of s2Um in formation of RNA-RNA and RNA DNA duplexes. The UV melting experiments revealed that RNA*-RNA and RNA*-DNA duplexes having an s2U-A base pair are more stable than those having a U-A base pair. On the contrary, the thermal stability of RNA*-RNA and RNA*-DNA duplexes having an s2U-G wobble base pair was much lower than that of the unmodified duplexes having a natural U-G base pair. It is concluded that s2Um has higher selectivity toward A over G than unmodified U.
Shohda
K
K
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Okamoto
I
I
Wada
T
T
Seio
K
K
Sekine
M
M
D001105:Archaea / Q000235:genetics; D020029:Base Pairing; D004247:DNA / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009692:Nucleic Acid Heteroduplexes; D009693:Nucleic Acid Hybridization; D009843:Oligoribonucleotides / Q000737:chemistry*; D020320:Oligoribonucleotides, Antisense; D012313:RNA / Q000737:chemistry; D013816:Thermodynamics; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
C409967:2'-O-methyl-2-thiouridine; D009692:Nucleic Acid Heteroduplexes; D009843:Oligoribonucleotides; D020320:Oligoribonucleotides, Antisense; D013891:Thiouridine; D012313:RNA; D004247:DNA