Zinc binding with l-dopa peptides

Zinc binding with l-dopa peptides

[Display omitted] •l-dopa is incorporated into a series of β-hairpin peptides.•The catechol of l-dopa is found to bind to zinc from spectroscopic, mass spectrometry and NMR investigations.•The binding stoichiometry of peptide and zinc is found to be 1:1 under the conditions examined.•Association ene...

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Bibliographic Details
Published in:Inorganica Chimica Acta Vol. 461; pp. 120 - 126
Main Authors: Veldkamp, Kelsey L., Tubergen, Philip J., Swartz, Mason A., DeVries, Jodie T., Tatko, Chad D.
Format: Journal Article
Language:English
Published: Amsterdam Elsevier B.V 01-05-2017
Elsevier Science Ltd
Subjects:
Binding
Dihydroxyphenylalanine
Homeostasis
Mass spectrometry
NMR
Nuclear magnetic resonance
Pathology
Peptide binding
Peptide bound l-dopa
Peptides
Spectrophotometry
Studies
Tyrosine
Zinc
Zinc chelation
Zinc complexes
Zinc compounds
β-Hairpin peptide
β-Hairpin peptide
Peptide bound l-dopa
Zinc complexes
Peptide binding
Zinc chelation
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Summary:[Display omitted] •l-dopa is incorporated into a series of β-hairpin peptides.•The catechol of l-dopa is found to bind to zinc from spectroscopic, mass spectrometry and NMR investigations.•The binding stoichiometry of peptide and zinc is found to be 1:1 under the conditions examined.•Association energies range from 4.3 to 5.2kcalmol−1. The combination of zinc dyshomoeostasis and oxidative damage has been linked to a number of human disease pathologies. A common pathway of oxidative damage centers on tyrosine with the generation of 3,4-dihydroxyphenylalanine (l-dopa). Once formed this catecholic moiety can be involved in metal binding. Herein, an l-dopa residue is incorporated into a peptide designed to adopt a β-hairpin configuration. Variation of the cross strand partner to l-dopa introduces an aromatic pair to enhance structure. Mass spectrometry indicates successful zinc binding, consistent with a 1:1 peptide:zinc complex. NMR and spectrophotometric investigations reveal the l-dopa as the binding locus with association energies ranging between 4.3 and 5.2kcalmol−1.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2017.02.006