Pb(II)-binding capability of aminohydroxamic acids

Primary hydroxamic acid derivatives of α-amino acids as possible sequestering agents for Pb(II)

Dávid Bátka, E. Farkas

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Complexes of aminohydroxamic acids, d,l-α-alaninehydroxamic acid (α-Alaha), sarcosinehydroxamic acid (Sarha), d,l-N-methyl-α- alaninehydroxamic acid (N-Me-α-Alaha), β-alaninehydroxamic (β-Alaha), l-aspartic acid-β-hydroxamic acid (Asp-β-ha), l-glutamic acid-γ-hydroxamic acid (Glu-γ-ha) and l-histidinehydroxamic acid (Hisha) with lead(II) in aqueous solution were studied by pH-potentiometric, 1H NMR and electrospray ionization mass spectrometric (ESI MS) methods. The results were compared to those of a simple monohydroxamic acid, acetohydroxamic acid and the effects of the amino group, hydroxamate-N, as well as, additional side chain donors on the co-ordination mode and on the stability of the complexes formed were evaluated. It was found that the amino nitrogen atom situating in β- or in γ-position (β-Alaha, Asp-β-ha, Glu-γ-ha) does not co-ordinate to Pb(II), only hydroxamate type chelates are formed before the hydrolytic processes. However, the amino-N in α-position (α-Alaha, Sarha, Hisha) seems to form a stable 5-membered (N,N)-type chelate together with the deprotonated hydroxamate-N above pH 6. On the other hand, the hydroxamate (O,O)-type chelate also exists. Since steric reasons do not allow the coordination of these two chelates of a molecule to the same Pb(II) ion, polynuclear complexes with mixed co-ordination modes are formed with the α-derivatives above pH 6. Simple hydroxamate type complexes are formed with N-Me-α-Alaha, where the hydroxamate-N is not able to co-ordinate. The co-ordination of the side chain imidazole of Hisha is not measurable, while a weak interaction of the side chain carboxylates of Asp-β-ha and especially of Glu-γ-ha can be suggested.

Original languageEnglish
Pages (from-to)27-35
Number of pages9
JournalJournal of Inorganic Biochemistry
Volume100
Issue number1
DOIs
Publication statusPublished - Jan 2006

Fingerprint

Sequestering Agents
Hydroxamic Acids
Derivatives
Amino Acids
Acids
Aspartic Acid
Glutamic Acid
Electrospray ionization
Nitrogen
Nuclear magnetic resonance
Ions
Atoms
Molecules

Keywords

  • Aminohydroxamic acid
  • Co-ordination chemistry
  • Pb(II) complexes
  • Stability constants

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

Cite this

@article{3756d6ba1e094403bd9a199dc19d744c,
title = "Pb(II)-binding capability of aminohydroxamic acids: Primary hydroxamic acid derivatives of α-amino acids as possible sequestering agents for Pb(II)",
abstract = "Complexes of aminohydroxamic acids, d,l-α-alaninehydroxamic acid (α-Alaha), sarcosinehydroxamic acid (Sarha), d,l-N-methyl-α- alaninehydroxamic acid (N-Me-α-Alaha), β-alaninehydroxamic (β-Alaha), l-aspartic acid-β-hydroxamic acid (Asp-β-ha), l-glutamic acid-γ-hydroxamic acid (Glu-γ-ha) and l-histidinehydroxamic acid (Hisha) with lead(II) in aqueous solution were studied by pH-potentiometric, 1H NMR and electrospray ionization mass spectrometric (ESI MS) methods. The results were compared to those of a simple monohydroxamic acid, acetohydroxamic acid and the effects of the amino group, hydroxamate-N, as well as, additional side chain donors on the co-ordination mode and on the stability of the complexes formed were evaluated. It was found that the amino nitrogen atom situating in β- or in γ-position (β-Alaha, Asp-β-ha, Glu-γ-ha) does not co-ordinate to Pb(II), only hydroxamate type chelates are formed before the hydrolytic processes. However, the amino-N in α-position (α-Alaha, Sarha, Hisha) seems to form a stable 5-membered (N,N)-type chelate together with the deprotonated hydroxamate-N above pH 6. On the other hand, the hydroxamate (O,O)-type chelate also exists. Since steric reasons do not allow the coordination of these two chelates of a molecule to the same Pb(II) ion, polynuclear complexes with mixed co-ordination modes are formed with the α-derivatives above pH 6. Simple hydroxamate type complexes are formed with N-Me-α-Alaha, where the hydroxamate-N is not able to co-ordinate. The co-ordination of the side chain imidazole of Hisha is not measurable, while a weak interaction of the side chain carboxylates of Asp-β-ha and especially of Glu-γ-ha can be suggested.",
keywords = "Aminohydroxamic acid, Co-ordination chemistry, Pb(II) complexes, Stability constants",
author = "D{\'a}vid B{\'a}tka and E. Farkas",
year = "2006",
month = "1",
doi = "10.1016/j.jinorgbio.2005.09.009",
language = "English",
volume = "100",
pages = "27--35",
journal = "Journal of Inorganic Biochemistry",
issn = "0162-0134",
publisher = "Elsevier Inc.",
number = "1",

}

TY - JOUR

T1 - Pb(II)-binding capability of aminohydroxamic acids

T2 - Primary hydroxamic acid derivatives of α-amino acids as possible sequestering agents for Pb(II)

AU - Bátka, Dávid

AU - Farkas, E.

PY - 2006/1

Y1 - 2006/1

N2 - Complexes of aminohydroxamic acids, d,l-α-alaninehydroxamic acid (α-Alaha), sarcosinehydroxamic acid (Sarha), d,l-N-methyl-α- alaninehydroxamic acid (N-Me-α-Alaha), β-alaninehydroxamic (β-Alaha), l-aspartic acid-β-hydroxamic acid (Asp-β-ha), l-glutamic acid-γ-hydroxamic acid (Glu-γ-ha) and l-histidinehydroxamic acid (Hisha) with lead(II) in aqueous solution were studied by pH-potentiometric, 1H NMR and electrospray ionization mass spectrometric (ESI MS) methods. The results were compared to those of a simple monohydroxamic acid, acetohydroxamic acid and the effects of the amino group, hydroxamate-N, as well as, additional side chain donors on the co-ordination mode and on the stability of the complexes formed were evaluated. It was found that the amino nitrogen atom situating in β- or in γ-position (β-Alaha, Asp-β-ha, Glu-γ-ha) does not co-ordinate to Pb(II), only hydroxamate type chelates are formed before the hydrolytic processes. However, the amino-N in α-position (α-Alaha, Sarha, Hisha) seems to form a stable 5-membered (N,N)-type chelate together with the deprotonated hydroxamate-N above pH 6. On the other hand, the hydroxamate (O,O)-type chelate also exists. Since steric reasons do not allow the coordination of these two chelates of a molecule to the same Pb(II) ion, polynuclear complexes with mixed co-ordination modes are formed with the α-derivatives above pH 6. Simple hydroxamate type complexes are formed with N-Me-α-Alaha, where the hydroxamate-N is not able to co-ordinate. The co-ordination of the side chain imidazole of Hisha is not measurable, while a weak interaction of the side chain carboxylates of Asp-β-ha and especially of Glu-γ-ha can be suggested.

AB - Complexes of aminohydroxamic acids, d,l-α-alaninehydroxamic acid (α-Alaha), sarcosinehydroxamic acid (Sarha), d,l-N-methyl-α- alaninehydroxamic acid (N-Me-α-Alaha), β-alaninehydroxamic (β-Alaha), l-aspartic acid-β-hydroxamic acid (Asp-β-ha), l-glutamic acid-γ-hydroxamic acid (Glu-γ-ha) and l-histidinehydroxamic acid (Hisha) with lead(II) in aqueous solution were studied by pH-potentiometric, 1H NMR and electrospray ionization mass spectrometric (ESI MS) methods. The results were compared to those of a simple monohydroxamic acid, acetohydroxamic acid and the effects of the amino group, hydroxamate-N, as well as, additional side chain donors on the co-ordination mode and on the stability of the complexes formed were evaluated. It was found that the amino nitrogen atom situating in β- or in γ-position (β-Alaha, Asp-β-ha, Glu-γ-ha) does not co-ordinate to Pb(II), only hydroxamate type chelates are formed before the hydrolytic processes. However, the amino-N in α-position (α-Alaha, Sarha, Hisha) seems to form a stable 5-membered (N,N)-type chelate together with the deprotonated hydroxamate-N above pH 6. On the other hand, the hydroxamate (O,O)-type chelate also exists. Since steric reasons do not allow the coordination of these two chelates of a molecule to the same Pb(II) ion, polynuclear complexes with mixed co-ordination modes are formed with the α-derivatives above pH 6. Simple hydroxamate type complexes are formed with N-Me-α-Alaha, where the hydroxamate-N is not able to co-ordinate. The co-ordination of the side chain imidazole of Hisha is not measurable, while a weak interaction of the side chain carboxylates of Asp-β-ha and especially of Glu-γ-ha can be suggested.

KW - Aminohydroxamic acid

KW - Co-ordination chemistry

KW - Pb(II) complexes

KW - Stability constants

UR - http://www.scopus.com/inward/record.url?scp=29444459260&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=29444459260&partnerID=8YFLogxK

U2 - 10.1016/j.jinorgbio.2005.09.009

DO - 10.1016/j.jinorgbio.2005.09.009

M3 - Article

VL - 100

SP - 27

EP - 35

JO - Journal of Inorganic Biochemistry

JF - Journal of Inorganic Biochemistry

SN - 0162-0134

IS - 1

ER -