Synthesis of 6-(2-thienyl)purine nucleoside derivatives that form unnatural base pairs with pyridin-2-one nucleosides.
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.
Fujiwara
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T
Yokoyama CytoLogic Project, ERATO, JST, c/o RIKEN, 2-1 Hirosawa, Wako-shi, 351-0198, Saitama, Japan.
Kimoto
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M
Sugiyama
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H
Hirao
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I
Yokoyama
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S
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
C435687:2-amino-6-(2-furanyl)purine; C435686:2-amino-6-(2-thienyl)purine; D005663:Furans; D011684:Purine Nucleosides; D011687:Purines