Photochemical ligation of DNA conjugates through anthracene cyclodimer formation and its fidelity to the template sequences

被引：72

作者：

Ihara, T ^{[1
]}

Fujii, T ^{[1
]}

Mukae, M ^{[1
]}

Kitamura, Y ^{[1
]}

Jyo, A ^{[1
]}

机构：

[1] Kumamoto Univ, Fac Engn, Dept Appl Chem & Biochem, Kumamoto 8608555, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 29期

关键词：

D O I：

10.1021/ja047784r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Anthracene readily forms photoadducts, anthracene dimers, and this photodimerization reaction has been well characterized. In general, however, the reaction requires close proximity and certain spatial alignment of both reaction partners. DNA could provide an ideal scaffold for accelerating the photocyclic addition. We synthesized a number of anthracene-DNA conjugates. The sequences of the conjugates, 5′AntODNn and 3′AntODNn (the length of methylene linkers: n = 3 or 6), were designed to bind adjacent sequences of the template with the anthracene units directed such that they stacked with each other. The conjugates were only dimerized in the presence of the template by light irradiation. The efficiency was affected by one-base displacement in the template sequence. Copyright © 2004 American Chemical Society.

引用

页码：8880 / 8881

页数：2

共 19 条

[1]

BOUASLAURENT H, 1990, PHOTOCHROMISM MOL SY, pCH14

[2] Nucleic acid template-directed assembly of metallosalen-DNA conjugates [J].

Czlapinski, JL ;

Sheppard, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8618-8619

[3] Template-directed photoreversible ligation of deoxyoligonucleotides via 5-vinyldeoxyuridine [J].

Fujimoto, K ;

Matsuda, S ;

Takahashi, N ;

Saito, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5646-5647

[4] Two enabling architectures for DNA-templated organic synthesis [J].

Gartner, ZJ ;

Grubina, R ;

Calderone, CT ;

Liu, DR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) :1370-1375

[5]

GILBERT A, 1991, ESSENTIALS MOL PHOTO, pCH8

[6] A COVALENT LOCK FOR SELF-ASSEMBLED OLIGONUCLEOTIDE CONJUGATES [J].

HERRLEIN, MK ;

NELSON, JS ;

LETSINGER, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (40) :10151-10152

[7] Colorimetric SNP analysis using oligonucleotide-modified nanoparticles [J].

Ihara, T ;

Chikaura, Y ;

Tanaka, S ;

Jyo, A .

CHEMICAL COMMUNICATIONS, 2002, (18) :2152-2153

[8] Mixed-phase hybridization of short Oligodeoxyribonucleotides on microscopic polymer particles:: Effect of one-base mismatches on duplex stability [J].

Ketomäki, K ;

Hakala, H ;

Lönnberg, H .

BIOCONJUGATE CHEMISTRY, 2002, 13 (03) :542-547

[9] Template-directed photoligation of oligodeoxyribonucleotides via 4-thiothymidine [J].

Liu, JQ ;

Taylor, JS .

NUCLEIC ACIDS RESEARCH, 1998, 26 (13) :3300-3304

[10] Programming the assembly of two- and three-dimensional architectures with DNA and nanoscale inorganic building blocks [J].

Mirkin, CA .

INORGANIC CHEMISTRY, 2000, 39 (11) :2258-2272

← 1 2 →