Nucleoside-Based Diarylethene Photoswitches and Their Facile Incorporation into Photoswitchable DNA

被引：97

作者：

Cahova, Hana ^{[1
]}

Jaeschke, Andres ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Pharm & Mol Biotechnol, D-69120 Heidelberg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 11期

关键词：

DNA damage; nucleosides; photochemistry; photoswitchable DNA; Suzuki cross-coupling; COVALENT MODIFICATION; POLYMERASE SYNTHESIS; FUNCTIONALIZED DNA; PHOTOREGULATION; TRIPHOSPHATES; AZOBENZENE; HYBRIDIZATION; TRANSCRIPTION; DERIVATIVES; PHOTOLYASE;

D O I：

10.1002/anie.201209943

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Come into the light: Pyrimidine nucleosides were found to undergo fast and reversible ring closure upon irradiation with light when covalently attached to 2-[2-methyl-5-phenylthien-3-yl]cyclopent-1-ene (see scheme). Synthesis using an aqueous-phase Suzuki-Miyaura cross-coupling allows for one-step conversion of iodo-modified oligonucleotides into fully reversible DNA photoswitches. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3186 / 3190

页数：5

共 40 条

[1]

[Anonymous], 2012, Angew. Chem

[2]

Asanuma H, 1999, ANGEW CHEM INT EDIT, V38, P2393, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2393::AID-ANIE2393>3.0.CO

[3]

2-7

[4]

Asanuma H., 1999, ANGEW CHEM INT EDIT, V111, P2547

[5] Covalent Modification of 2′-Deoxyuridine with Two Different Molecular Switches [J].

Barrois, Sebastian ;

Beyer, Christoph ;

Wagenknecht, Hans-Achim .

SYNLETT, 2012, (05) :711-716

[6] Azobenzene photoswitches for biomolecules [J].

Beharry, Andrew A. ;

Woolley, G. Andrew .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (08) :4422-4437

[7] Synthesis of DNA with Spirobenzopyran as an Internal Covalent Modification [J].

Beyer, Christoph ;

Wagenknecht, Hans-Achim .

SYNLETT, 2010, (09) :1371-1376

[8] Light-Controlled Tools [J].

Brieke, Clara ;

Rohrbach, Falk ;

Gottschalk, Alexander ;

Mayer, Guenter ;

Heckel, Alexander .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (34) :8446-8476

[9]

Cahova H., 2008, Angewandte Chemie, V120, P2089, DOI DOI 10.1002/ANGE.200705088

[10] Aminophenyl- and nitrophenyl-labeled nucleoside triphosphates:: Synthesis, enzymatic incorporation, and electrochemical detection [J].

Cahova, Hana ;

Havran, Ludek ;

Brazdilova, Petra ;

Pivonkova, Hana ;

Pohl, Radek ;

Fojta, Miroslav ;

Hocek, Michal .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2059-2062

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