A cleavable amino-thiol linker for reversible linking of amines to DNA

被引:13
作者
Hojfeldt, Jonas W.
Blakskjær, Peter
Gothelf, Kurt V.
机构
[1] Univ Aarhus, Dept Chem, Ctr Catalysis & Interdisciplinary Nanosci Ctr, iNANO, DK-8000 Aarhus C, Denmark
[2] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[3] Vipergen, DK-2100 Copenhagen OE, Denmark
关键词
D O I
10.1021/jo0619736
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cleavable heterobifunctional cross-linker for the reversible conjugation of amines to thiol-modified DNA has been developed and tested. The succinimidyl 2-(vinylsulfonyl)-ethyl carbonate (SVEC) was prepared in three steps and tested for its ability to react with amines and thiols. The linker was efficient for binding leucine to a thiol-modified DNA sequence and for releasing the amino acid at pH 11.8.
引用
收藏
页码:9556 / 9559
页数:4
相关论文
共 17 条
[1]   Synthesis of an elongated linear oligo(phenyleneethynylene)-based building block for application in DNA-programmed assembly [J].
Blakskjaer, Peter ;
Gothelf, Kurt V. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (18) :3442-3447
[2]   Self-assembly of aluminium-salen coupled nanostructures from encoded modules with cleavable disulfide DNA-linkers [J].
Brown, RS ;
Nielsen, M ;
Gothelf, KV .
CHEMICAL COMMUNICATIONS, 2004, (13) :1464-1465
[3]   DNA-programmed control of photosensitized singlet oxygen production [J].
Cló, E ;
Snyder, JW ;
Voigt, NV ;
Ogilby, PR ;
Gothelf, KV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) :4200-4201
[4]   DNA-templated organic synthesis and selection of a library of macrocycles [J].
Gartner, ZJ ;
Tse, BN ;
Grubina, R ;
Doyon, JB ;
Snyder, TM ;
Liu, DR .
SCIENCE, 2004, 305 (5690) :1601-1605
[5]   N,N'-DISUCCINIMIDYL CARBONATE - A USEFUL REAGENT FOR ALKOXYCARBONYLATION OF AMINES [J].
GHOSH, AK ;
DUONG, TT ;
MCKEE, SP ;
THOMPSON, WJ .
TETRAHEDRON LETTERS, 1992, 33 (20) :2781-2784
[6]   Convenient synthesis of novel macrocyclic urethanes: Alkoxycarbonylation of amines and ring-closing metathesis strategy [J].
Ghosh, AK ;
Hussain, KA .
TETRAHEDRON LETTERS, 1998, 39 (14) :1881-1884
[7]   DNA-programmed assembly of nanostructures [J].
Gothelf, KV ;
LaBean, TH .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (22) :4023-4037
[8]   A modular approach to DNA-programmed self-assembly of macromolecular nanostructures [J].
Gothelf, KV ;
Brown, RS .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (04) :1062-1069
[9]   Modular DNA-programmed assembly of linear and branched conjugated nanostructures [J].
Gothelf, KV ;
Thomsen, A ;
Nielsen, M ;
Cló, E ;
Brown, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (04) :1044-1046
[10]   Femtomolar electrochemical detection of DNA targets using metal sulfide nanoparticles [J].
Hansen, JA ;
Mukhopadhyay, R ;
Hansen, JO ;
Gothelf, KV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3860-3861