DNA-based phosphane ligands

被引:29
作者
Caprioara, Mihaela
Fiammengo, Roberto
Engeser, Marianne
Jaeschke, Andres
机构
[1] Univ Heidelberg, Inst Pharm & Mol Biotechnol, D-69120 Heidelberg, Germany
[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
关键词
DNA; nucleic acids; oxazoline; phosphane ligands;
D O I
10.1002/chem.200601058
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In order to expand the repertoire of DNA sequences specifically interacting with transition metals, we report here the first examples of DNA sequences carrying mono- and bidentate phosphane ligands as well as P,N-ligands. Aminoalkyl-modified oligonucleotides have been reacted at predetermined internal sites with carboxylate derivatives of pyrphos, BINAP and phosphinooxazoline (PHOX) 2b-d. Carbodiimide coupling in the presence of N-hydroxysuccinimide provided the DNA-ligand conjugates in 38-78% yield. Phosphane-containing oligonucleotides and their phosphane sulfide analogues were characterized by mass spectrometry (MALDI-TOF and FT-ICR-ESI) and their stability after purification and isolation was systematically investigated. While DNA-appended pyrphos ligand was quickly oxidized, BINAP and PHOX conjugates showed high stabilities, making them useful precursors for incorporation of transition metals into DNA.
引用
收藏
页码:2089 / 2095
页数:7
相关论文
共 60 条
[1]   SEQUENCE-SPECIFIC CLEAVAGE OF HIV MESSENGER-RNA BY A RIBOZYME MIMIC [J].
BASHKIN, JK ;
FROLOVA, EI ;
SAMPATH, US .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5981-5982
[2]   Immobilization of rhodium complexes at thiolate monolayers on gold surfaces:: Catalytic and structural studies [J].
Belser, T ;
Stöhr, M ;
Pfaltz, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8720-8731
[3]   PRECISION SEQUENCE-SPECIFIC CLEAVAGE OF A NUCLEIC-ACID BY A MINOR-GROOVE-DIRECTED METAL-BINDING LIGAND LINKED THROUGH N-2 OF DEOXYGUANOSINE [J].
BERGSTROM, DE ;
GERRY, NP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12067-12068
[4]   Directed DNA metallization [J].
Burley, GA ;
Gierlich, J ;
Mofid, MR ;
Nir, H ;
Tal, S ;
Eichen, Y ;
Carell, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1398-1399
[5]   A highly DNA-duplex-stabilizing metal-salen base pair [J].
Clever, GH ;
Polborn, K ;
Carell, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7204-7208
[6]   Artificial metalloenzymes for enantioselective catalysis based on biotin-avidin [J].
Collot, J ;
Gradinaru, J ;
Humbert, N ;
Skander, M ;
Zocchi, A ;
Ward, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9030-9031
[7]   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
[8]   SEQUENCE-SPECIFIC CLEAVAGE OF SINGLE-STRANDED-DNA - OLIGODEOXYNUCLEOTIDE-EDTA.FE(II) [J].
DREYER, GB ;
DERVAN, PB .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1985, 82 (04) :968-972
[9]  
Engel GD, 2002, CHEM-EUR J, V8, P4319, DOI 10.1002/1521-3765(20020916)8:18<4319::AID-CHEM4319>3.0.CO
[10]  
2-L