Volume 32, Issue 45
Natural Products
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ChemInform Abstract: Synthesis of 6-(2-Thienyl)purine Nucleoside Derivatives That Form Unnatural Base Pairs with Pyridin-2-one Nucleosides.

Tsuyoshi Fujiwara

Tsuyoshi Fujiwara

Yokoyama CytoLogic Project, ERATO, Japan Sci. Technol. Corp., RIKEN, Wako 351-0198, Japan

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Michiko Kimoto

Michiko Kimoto

Yokoyama CytoLogic Project, ERATO, Japan Sci. Technol. Corp., RIKEN, Wako 351-0198, Japan

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Hiroshi Sugiyama

Hiroshi Sugiyama

Yokoyama CytoLogic Project, ERATO, Japan Sci. Technol. Corp., RIKEN, Wako 351-0198, Japan

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Ichiro Hirao

Ichiro Hirao

Yokoyama CytoLogic Project, ERATO, Japan Sci. Technol. Corp., RIKEN, Wako 351-0198, Japan

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Shigeyuki Yokoyama

Shigeyuki Yokoyama

Yokoyama CytoLogic Project, ERATO, Japan Sci. Technol. Corp., RIKEN, Wako 351-0198, Japan

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First published: 23 May 2010

Abstract

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ChemInform Abstract

The unnatural nucleosides (III) as well as the amidite (IX) are prepared for DNA synthesis. Base (IV) reduces the interference in the stacking interactions with the neighboring bases in a DNA duplex and improves the efficiency of the enzymatic incorporation of the nucleoside triphosphate of pyridin-2-one opposite the unnatural base. The furanyl derivatives (IIIa) and (IIIc) gradually decomposes under the basic conditions used in DNA synthesis.

chemical structure image

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