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A Unique Fluorescent Base Analogue for the Expansion of the Genetic Alphabet

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Michiko Kimoto^†^‡, Tsuneo Mitsui^‡, Shigeyuki Yokoyama^†^§ and Ichiro Hirao*^†^‡

RIKEN Systems and Structural Biology Center (SSBC) and TagCyx Biotechnologies, 1-7-22 Suehiro-cho, Tsurumi-ku, Yokohama, Kanagawa 230-0045, Japan, and Department of Biophysics and Biochemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

J. Am. Chem. Soc., 2010, 132 (14), pp 4988–4989

DOI: 10.1021/ja100806c

Publication Date (Web): March 24, 2010

ihirao@riken.jp, †

RIKEN Systems and Structural Biology Center.

, ‡

TagCyx Biotechnologies.

, §

The University of Tokyo.

Section:

Carbohydrates

Abstract

Fluorescent nucleobase analogues are useful in a wide variety of biology and biotechnology tools as molecular probes and reporters for nucleic acids. Here we present a novel fluorescent purine analogue, 7-(2,2′-bithien-5-yl)-imidazo[4,5-b]pyridine (denoted as Dss). The nucleoside triphosphates of Dss can be site-specifically incorporated into DNA and RNA by polymerases, opposite its pairing partner, pyrrole-2-carbaldehyde (Pa), in DNA templates. Despite its high specificity in replication and transcription, Dss in oligonucleotides functions as a universal base that pairs with all four natural bases with nearly equal thermal stabilities. Thus, Dss would be a powerful tool for fluorescent base replacements at specific positions in functional DNA and RNA molecules.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Novel Modifications in RNA
Kelly Phelps, Alexi Morris, and Peter A. Beal
ACS Chemical Biology2012 7 (1), 100-109
- Novel Modifications in RNA
  Kelly Phelps, Alexi Morris, and Peter A. Beal
  ACS Chemical Biology2012 7 (1), 100-109
  The past several years have seen numerous reports of new chemical modifications for use in RNA. In addition, in that time period, we have seen the discovery of several previously unknown naturally occurring modifications that impart novel properties on ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
A New Unnatural Base Pair System between Fluorophore and Quencher Base Analogues for Nucleic Acid-Based Imaging Technology
Michiko Kimoto, Tsuneo Mitsui, Rie Yamashige, Akira Sato, Shigeyuki Yokoyama, and Ichiro Hirao
Journal of the American Chemical Society2010 132 (43), 15418-15426
- A New Unnatural Base Pair System between Fluorophore and Quencher Base Analogues for Nucleic Acid-Based Imaging Technology
  Michiko Kimoto, Tsuneo Mitsui, Rie Yamashige, Akira Sato, Shigeyuki Yokoyama, and Ichiro Hirao
  Journal of the American Chemical Society2010 132 (43), 15418-15426
  In the development of orthogonal extra base pairs for expanding the genetic alphabet, we created novel, unnatural base pairs between fluorophore and quencher nucleobase analogues. We found that the nucleobase analogue, 2-nitropyrrole (denoted by Pn), and ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links