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

被引：60

作者：

Kimoto, Michiko ^{[1
,2
]}

Mitsui, Tsuneo ^{[2
]}

Yokoyama, Shigeyuki ^{[1
,3
]}

Hirao, Ichiro ^{[1
,2
]}

机构：

[1] RIKEN, SSBC, Tsurumi Ku, Kanagawa 2300045, Japan

[2] TagCyx Biotechnol, Tsurumi Ku, Kanagawa 2300045, Japan

[3] Univ Tokyo, Grad Sch Sci, Dept Biophys & Biochem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 14期

关键词：

DNA-REPLICATION FIDELITY; PAIR SYSTEM; RNA;

D O I：

10.1021/ja100806c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：4988 / +

页数：4

共 17 条

[1] Development and applications of fluorescent oligonucleotides [J].

Asseline, U .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (04) :491-518

[2] Nucleic Acid Base Analog FRET-Pair Facilitating Detailed Structural Measurements in Nucleic Acid Containing Systems [J].

Borjesson, Karl ;

Preus, Soren ;

El-Sagheer, Afaf H. ;

Brown, Tom ;

Albinsson, Bo ;

Wilhelmsson, L. Marcus .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (12) :4288-4293

[3] EFFECT OF END SUBSTITUTION ON ELECTROCHEMICAL AND OPTICAL-PROPERTIES OF OLIGOTHIOPHENES [J].

GARCIA, P ;

PERNAUT, JM ;

HAPIOT, P ;

WINTGENS, V ;

VALAT, P ;

GARNIER, F ;

DELABOUGLISE, D .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (02) :513-516

[4] BIOCHEMICAL BASIS OF DNA-REPLICATION FIDELITY [J].

GOODMAN, MF ;

CREIGHTON, S ;

BLOOM, LB ;

PETRUSKA, J .

CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1993, 28 (02) :83-126

[5] A two-unnatural-base-pair system toward the expansion of the genetic code [J].

Hirao, I ;

Harada, Y ;

Kimoto, M ;

Mitsui, T ;

Fujiwara, T ;

Yokoyama, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (41) :13298-13305

[6] An unnatural hydrophobic base pair system: site-specific incorporation of nucleotide analogs into DNA and RNA [J].

Hirao, Ichiro ;

Kimoto, Michiko ;

Mitsui, Tsuneo ;

Fujiwara, Tsuyoshi ;

Kawai, Rie ;

Sato, Akira ;

Harada, Yoko ;

Yokoyama, Shigeyuki .

NATURE METHODS, 2006, 3 (09) :729-735

[7] A quantitative, non-radioactive single-nucleotide insertion assay for analysis of DNA replication fidelity by using an automated DNA sequencer [J].

Kimoto, M ;

Yokoyama, S ;

Hirao, I .

BIOTECHNOLOGY LETTERS, 2004, 26 (12) :999-1005

[8] Fluorescent probing for RNA molecules by an unnatural base-pair system [J].

Kimoto, Michiko ;

Mitsui, Tsuneo ;

Harada, Yoko ;

Sato, Akira ;

Yokoyama, Shigeyuki ;

Hirao, Ichiro .

NUCLEIC ACIDS RESEARCH, 2007, 35 (16) :5360-5369

[9] An unnatural base pair system for efficient PCR amplification and functionalization of DNA molecules [J].

Kimoto, Michiko ;

Kawai, Rie ;

Mitsui, Tsuneo ;

Yokoyama, Shigeyuki ;

Hirao, Ichiro .

NUCLEIC ACIDS RESEARCH, 2009, 37 (02)

[10] Fluorescence of size-expanded DNA bases: Reporting on DNA sequence and structure with an unnatural genetic set [J].

Krueger, Andrew T. ;

Kool, Eric T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) :3989-3999

← 1 2 →