title: Synthesis of 6-(2-thienyl)purine nucleoside derivatives that form unnatural base pairs with pyridin-2-one nucleosides.
abstract: Unnatural bases, 2-amino-6-(2-thienyl)purine and 2-amino-6-(2-furanyl)purine, were newly designed to replace the previously developed purine analogue, 2-amino-6-(N,N-dimethylamino)purine, which specifically pairs with pyridin-2-one. These nucleoside derivatives were synthesized via the 6-substitution of 6-iodopurine nucleosides with tributylstannylthiophene or tributylstannylfuran. As compared with 2-amino-6-(N,N-dimethylamino)purine, 2-amino-6-(2-thienyl)purine reduced the interference in the stacking interactions with the neighboring bases in a DNA duplex and improved the efficiency of the enzymatic incorporation of the nucleoside triphosphate of pyridin-2-one opposite the unnatural base.
authors.affiliation: Yokoyama CytoLogic Project, ERATO, JST, c/o RIKEN, 2-1 Hirosawa, Wako-shi, 351-0198, Saitama, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Fujiwara
authors.forename: M
authors.initials: M
authors.lastname: Kimoto
authors.forename: H
authors.initials: H
authors.lastname: Sugiyama
authors.forename: I
authors.initials: I
authors.lastname: Hirao
authors.forename: S
authors.initials: S
authors.lastname: Yokoyama
mesh_terms: D020029:Base Pairing; D005663:Furans / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009691:Nucleic Acid Denaturation; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000737:chemistry
chemical_list: C435687:2-amino-6-(2-furanyl)purine; C435686:2-amino-6-(2-thienyl)purine; D005663:Furans; D011684:Purine Nucleosides; D011687:Purines