Synthesis of 6-(2-thienyl)purine nucleoside derivatives toward the expansion of the genetic code.
Unnatural bases specifically pairing with pyridin-2-one, 2-amino-6-(2-thienyl) purine and 2-amino-6-(2-furanyl)purine, were newly designed to replace 2-amino-6-(N,N-dimethylamino)purine. It was expected that these novel purine analogues, as compared with 2-amino-6-(N,N-dimethylamino)purine, might reduce the interference in the stacking interactions with the neighboring bases in a duplex and improve the efficiency of the enzymatic incorporation of the nucleoside triphosphate of pyridin-2-one opposite these unnatural bases. The syntheses of these nucleoside derivatives and the DNA fragments were examined.
Fujiwara
T
T
Yokoyama CytoLogic Project, ERATO, JST, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
Sugiyama
H
H
Hirao
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I
Yokoyama
S
S
D020029:Base Pairing; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry / Q000235:genetics; D003853:Deoxyribonucleosides / Q000138:chemical synthesis / Q000737:chemistry; D005815:Genetic Code; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D003853:Deoxyribonucleosides; D011684:Purine Nucleosides; D004247:DNA