Synthesis and characterization of CuII complexes with amino acid substituted di(2-pyridyl)amine ligands

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Abstract

The two-step syntheses of the substituted di(2-pyridyl)amine ligands (dpa), dpa-CH2CO2H (1) and dpa-PhCO2H (2), are described. Ligands 1 and 2 are successfully coupled to the amino acid phenylalanine, yielding the derivatives 4 and 6, respectively. Four Cu II(dpa)2 complexes, [Cu(dpa-CH2CO 2tBu)2(NO3)2] (3Cu), [Cu(dpa-CH2CO-PheOMe)2(H2O)2] (NO3)2·2MeOH (4Cu), [Cu(dpa-PhCO 2Me)2 (MeOH)2](ClO4)2 (5Cu) and [Cu(dpa-PhCO-PheOMe)2(ClO4) 2] (6Cu) have been prepared and characterized, including their single crystal X-ray structures. Fluorescence emission at UV (for 3 and 4) or blue (for 5 and 6) wavelengths of the free ligands is preserved in the corresponding Cu complexes, although with lower intensity. X-band EPR spectra of 4Cu and 6Cu both revealed one axial CuII signal with hyperfine and superhyperfine splittings. Complexes 4Cu and 6Cu are chiral inorganic complexes with amino acid bioconjugates that may serve as nucleoside analogs in modified peptide nucleic acids (PNA).

Original languageEnglish (US)
Pages (from-to)3686-3694
Number of pages9
JournalEuropean Journal of Inorganic Chemistry
Issue number23
DOIs
StatePublished - Aug 27 2007

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Amines
Ligands
Amino Acids
Peptide Nucleic Acids
Phenylalanine
Nucleosides
Paramagnetic resonance
Fluorescence
Single crystals
Derivatives
X rays
Wavelength
perchlorate

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

@article{36fd330b9b304b6e89f42cde01a18242,
title = "Synthesis and characterization of CuII complexes with amino acid substituted di(2-pyridyl)amine ligands",
abstract = "The two-step syntheses of the substituted di(2-pyridyl)amine ligands (dpa), dpa-CH2CO2H (1) and dpa-PhCO2H (2), are described. Ligands 1 and 2 are successfully coupled to the amino acid phenylalanine, yielding the derivatives 4 and 6, respectively. Four Cu II(dpa)2 complexes, [Cu(dpa-CH2CO 2tBu)2(NO3)2] (3Cu), [Cu(dpa-CH2CO-PheOMe)2(H2O)2] (NO3)2·2MeOH (4Cu), [Cu(dpa-PhCO 2Me)2 (MeOH)2](ClO4)2 (5Cu) and [Cu(dpa-PhCO-PheOMe)2(ClO4) 2] (6Cu) have been prepared and characterized, including their single crystal X-ray structures. Fluorescence emission at UV (for 3 and 4) or blue (for 5 and 6) wavelengths of the free ligands is preserved in the corresponding Cu complexes, although with lower intensity. X-band EPR spectra of 4Cu and 6Cu both revealed one axial CuII signal with hyperfine and superhyperfine splittings. Complexes 4Cu and 6Cu are chiral inorganic complexes with amino acid bioconjugates that may serve as nucleoside analogs in modified peptide nucleic acids (PNA).",
author = "Kirin, {Srećko I.} and Yennawar, {Hemant P.} and Williams, {Mary Elizabeth}",
year = "2007",
month = "8",
day = "27",
doi = "10.1002/ejic.200700273",
language = "English (US)",
pages = "3686--3694",
journal = "Chemische Berichte",
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T1 - Synthesis and characterization of CuII complexes with amino acid substituted di(2-pyridyl)amine ligands

AU - Kirin, Srećko I.

AU - Yennawar, Hemant P.

AU - Williams, Mary Elizabeth

PY - 2007/8/27

Y1 - 2007/8/27

N2 - The two-step syntheses of the substituted di(2-pyridyl)amine ligands (dpa), dpa-CH2CO2H (1) and dpa-PhCO2H (2), are described. Ligands 1 and 2 are successfully coupled to the amino acid phenylalanine, yielding the derivatives 4 and 6, respectively. Four Cu II(dpa)2 complexes, [Cu(dpa-CH2CO 2tBu)2(NO3)2] (3Cu), [Cu(dpa-CH2CO-PheOMe)2(H2O)2] (NO3)2·2MeOH (4Cu), [Cu(dpa-PhCO 2Me)2 (MeOH)2](ClO4)2 (5Cu) and [Cu(dpa-PhCO-PheOMe)2(ClO4) 2] (6Cu) have been prepared and characterized, including their single crystal X-ray structures. Fluorescence emission at UV (for 3 and 4) or blue (for 5 and 6) wavelengths of the free ligands is preserved in the corresponding Cu complexes, although with lower intensity. X-band EPR spectra of 4Cu and 6Cu both revealed one axial CuII signal with hyperfine and superhyperfine splittings. Complexes 4Cu and 6Cu are chiral inorganic complexes with amino acid bioconjugates that may serve as nucleoside analogs in modified peptide nucleic acids (PNA).

AB - The two-step syntheses of the substituted di(2-pyridyl)amine ligands (dpa), dpa-CH2CO2H (1) and dpa-PhCO2H (2), are described. Ligands 1 and 2 are successfully coupled to the amino acid phenylalanine, yielding the derivatives 4 and 6, respectively. Four Cu II(dpa)2 complexes, [Cu(dpa-CH2CO 2tBu)2(NO3)2] (3Cu), [Cu(dpa-CH2CO-PheOMe)2(H2O)2] (NO3)2·2MeOH (4Cu), [Cu(dpa-PhCO 2Me)2 (MeOH)2](ClO4)2 (5Cu) and [Cu(dpa-PhCO-PheOMe)2(ClO4) 2] (6Cu) have been prepared and characterized, including their single crystal X-ray structures. Fluorescence emission at UV (for 3 and 4) or blue (for 5 and 6) wavelengths of the free ligands is preserved in the corresponding Cu complexes, although with lower intensity. X-band EPR spectra of 4Cu and 6Cu both revealed one axial CuII signal with hyperfine and superhyperfine splittings. Complexes 4Cu and 6Cu are chiral inorganic complexes with amino acid bioconjugates that may serve as nucleoside analogs in modified peptide nucleic acids (PNA).

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