title: Synthesis and properties of thymidines with six-membered amide bridge.
abstract: Artificial thymidine monomers possessing amide or N-methylamide bridges were designed, synthesized, and introduced into oligonucleotides. UV-melting experiments showed that these oligonucleotides preferred single-stranded RNA (ssRNA) to single-stranded DNA (ssDNA) in duplex formation. Both amide- and N-methylamide-modified oligonucleotides led to a significant increase in the binding affinity to ssRNA by up to +4.7 and +3.7°C of the Tm value per modification, respectively, compared with natural oligonucleotide. In addition, their oligonucleotides showed high stability against 3'-exonuclease.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Hari
authors.forename: Takashi
authors.initials: T
authors.lastname: Osawa
authors.forename: Yutaro
authors.initials: Y
authors.lastname: Kotobuki
authors.forename: Aiko
authors.initials: A
authors.lastname: Yahara
authors.forename: Ajaya R
authors.initials: AR
authors.lastname: Shrestha
authors.forename: Satoshi
authors.initials: S
authors.lastname: Obika
mesh_terms: D000577:Amides / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D015195:Drug Design; D015394:Molecular Structure; D012313:RNA / Q000737:chemistry*; D013936:Thymidine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D012313:RNA; D004247:DNA; D013936:Thymidine