A new route to 2'-O-alkyl-2-thiouridine derivatives via 4-O-protection of the uracil base and hybridization properties of oligonucleotides incorporating these modified nucleoside derivatives.
Oligonucleotides containing 2-thiouridine (s2U) in place of uridine form stable RNA duplexes with complementary RNAs. Particularly, this modified nucleoside has proved to recognize highly selectively adenosine, the genuine partner, without formation of a mismatched base pair with the guanosine counterpart. In this paper, we describe new methods for the synthesis of 2-thiouridine and various 2'-O-alkyl-2-thiouridine derivatives. Oligoribonucleotides having these modified nucleoside derivatives were synthesized, and their hybridization and structural properties were studied in detail by the 1H NMR analysis of these modified nucleosides and Tm experiments of RNA duplexes with their complementary RNA strands.
Okamoto
Itaru
I
Department of Life Science and Frontier Collaborative Research Center, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8501, Japan.
Shohda
Koh-ichiroh
K
Seio
Kohji
K
Sekine
Mitsuo
M
D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis; D018075:RNA, Complementary / Q000737:chemistry; D013696:Temperature; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000737:chemistry*
D009692:Nucleic Acid Heteroduplexes; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D018075:RNA, Complementary; C434331:phosphoramidite; D013891:Thiouridine; D014498:Uracil