A second-generation copper(II)-mediated metallo-DNA-base pair

Bioorganic Chemistry

Volumn 32, Issue 1, 2004, Pages 13-25

  Zimmermann, Nicole ^a   Meggers, Eric ^a   Schultz, Peter G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Alternative binding schemes; Copper(II); Metallo DNA base pairs; Nucleobases; Tridentate pyridine ligands

Indexed keywords

(5 BROMO 6 HYDROXYMETHYLPYRIDIN 2 YL)METHANOL; 2 [4 METHOXYBENZYLOXY (4 METHOXYBENZYLOXYMETHYL)TETRAHYDROFURANYL]PYRIDINE 2,6 DICARBOXYLIC ACID; 2,6 BIS(TERT BUTYLDIMETHYLSILANYLOXYMETHYL) 3 [4 METHOXYBENZYLOXY (4 METHOXYBENZYLOXYMETHYL)TETRAHYDROFURANYL]PYRIDINE; 3 (HYDROXYHYDROXYMETHYLTETRAHYDROFURANYL)PYRIDINE 2,6 DICARBOXYLIC ACID DIMETHYL ESTER; 3 BROMO 2,6 BIS(TERT BUTYLDIMETHYLSILANYLOXYMETHYL)PYRIDINE; 3 BROMO 2,6 DIMETHYLPYRIDINE; 3 BROMOPYRIDINE 2,6 DICARBOXYLIC ACID DIMETHYL ESTER; 3 [4 METHOXYBENZYLOXY (4 METHOXYBENZYLOXYMETHYL)TETRAHYDROFURANYL]PYRIDINE 2,6 DICARBOXYLIC ACID DIMETHYL ESTER; 3 [[BIS(4 METHOXYPHENYL)PHENYLMETHOXYMETHYL]HYDROXYTETRAHYDROFURANYL]PYRIDINE 2,6 DICARBOXYLIC ACID DIMETHYL ESTER; 3 [[BIS(4 METHOXYPHENYL)PHENYLMETHOXYMETHYL][(2 CYANOETHOXY)DIISOPROPYLAMINOPHOSPHANYLOXY]TETRAHYDROFURANYL]PYRIDINE 2,6 DICARBOXYLIC ACID DIMETHYL ESTER; COPPER ION; DIPICOLINIC ACID; DNA BASE; DOUBLE STRANDED DNA; HYDROGEN; METAL; NUCLEIC ACID BASE; PYRIDINE 2,6 DICARBOXAMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; [2,6 BIS(TERT BUTYLDIMETHYLSILANYLOXYMETHYL)PYRIDIN 3 YL] 5 TRIS(4 METHOXYBENZYLOXY)PENTAN 1 OL; [6 HYDROXYMETHYL 5 [4 METHOXYBENZYLOXY (4 METHOXYBENZYLOXYMETHYL)TETRAHYDROFURANYL]PYRIDIN 2 YL]METHANOL;

ARTICLE; BASE MISPAIRING; BASE PAIRING; CHEMICAL REACTION; HYDROGEN BOND; PRIORITY JOURNAL; SYNTHESIS;

EID: 0346970894     PISSN: 00452068     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioorg.2003.09.001     Document Type: Article

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25. Yield is given after purification by reversed phase HPLC. Identities were confirmed by MALDI-TOF MS. 15-mer oligonucleotides containing Dipic-Ester or Me-Dipam have the same mass but could be distinguished by their different retention times using reversed phase HPLC.
26. m -values reported herein were confirmed by repeated experiments and were consistent under the experimental conditions reported here.
27. m=28.0 °C) which is not the case for the Dipic:Py base pair. This stabilizing effect may be caused by weak hydrogen bonding interactions. It might also explain the observed difference in required metal ion concentrations of both metallo-base pairs due to different kinetics for the formation of the corresponding metal complexes.
28. Shionoya and coworkers recently reported a self-assembled metal array in artificial DNA consisting of copper(II)-mediated base pairs between hydroxypyridone nucleobases: Tanaka K., Tengeiji A., Kato T., Toyama N., Shionoya M. Science. 299:2003;1212-1213.
29. Conditions: 5 mM sodium phosphate, 50 mM sodium perchlorate, pH 7, 1 μM DNA duplex, 30 μM (15a/b)/60 μM (16a/b) copper(II) acetate.
30. 2+ ions.