The first chemical synthesis of boronic acid-modified DNA through a copper-free click reaction

被引：25

作者：

Dai, Chaofeng

Wang, Lifang

Sheng, Jia

Peng, Hanjing

Draganov, Alexander Boryanov

Huang, Zhen

Wang, Binghe ^{[1
]}

机构：

[1] Georgia State Univ, Dept Chem, Atlanta, GA 30302 USA

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 12期

基金：

美国国家卫生研究院;

关键词：

CYCLOADDITION REACTION; TERMINAL ALKYNES; CHEMISTRY; DESIGN; AZIDES;

D O I：

10.1039/c0cc04546b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first chemical incorporation of the boronic acid group into DNA using a copper-free click reagent was reported. Compared with the PCR-based method, this approach allows for site-specific incorporation and synthesis on a larger scale.

引用

页码：3598 / 3600

页数：3

共 24 条

[1] Cu(I)-Catalyzed Huisgen Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry [J].

Amblard, Franck ;

Cho, Jong Hyun ;

Schinazi, Raymond F. .

CHEMICAL REVIEWS, 2009, 109 (09) :4207-4220

[2]

Blackburn GM, 2006, NUCLEIC ACIDS IN CHEMISTRY AND BIOLOGY, THIRD EDITION, pV, DOI 10.1039/9781847555380

[3]

Bloomfield V., 2000, NUCL ACIDS STRUCTURE

[4] Amino-functionalized DNA:: the properties of C5-amino-alkyl substituted 2′-deoxyuridines and their application in DNA triplex formation [J].

Brazier, JA ;

Shibata, T ;

Townsley, J ;

Taylor, BF ;

Frary, E ;

Williams, NH ;

Williams, DM .

NUCLEIC ACIDS RESEARCH, 2005, 33 (04) :1362-1371

[5] Second-generation difluorinated cyclooctynes for copper-free click chemistry [J].

Codelli, Julian A. ;

Baskin, Jeremy M. ;

Agard, Nicholas J. ;

Berozzi, Carolyn R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11486-11493

[6] RIBONUCLEOSIDES AND RNA [J].

EATON, BE ;

PIEKEN, WA .

ANNUAL REVIEW OF BIOCHEMISTRY, 1995, 64 :837-863

[7] Boronic acids in molecular self-assembly [J].

Fujita, Norifumi ;

Shinkai, Seiji ;

James, Tony D. .

CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (07) :1076-1091

[8] Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA [J].

Gierlich, Johannes ;

Burley, Glenn A. ;

Gramlich, Philipp M. E. ;

Hammond, David M. ;

Carell, Thomas .

ORGANIC LETTERS, 2006, 8 (17) :3639-3642

[9] Postsynthetic DNA Modification through the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction [J].

Gramlich, Philipp M. E. ;

Wirges, Christian T. ;

Manetto, Antonio ;

Carell, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8350-8358

[10]

Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548

← 1 2 3 →