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An examination of the binding behavior of histidine-containing peptides with immobilized metal complexes derived from the macrocyclic ligand, 1,4,7-triazacyclononane

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Abstract

In this study, two different experimental approaches have been employed to examine the binding behavior of histidine-containing peptides with metal ion complexes derived from the macrocyclic ligand 1,4,7-triazacyclononane (tacn). Firstly, a molecular modeling approach has been employed to derive the strain energies for test peptide sequences that have a predicted propensity to readily adopt an α-helical conformation. To this end, binuclear metal complexes were examined with peptides containing two histidine residues in different locations in a pair of peptides of the same composition but different sequence. These modeling results indicate that there are no energetic constraints for two-point binding to occur with dicopper(II) binuclear complexes when two histidine residues are appropriately placed in an α-helical conformation. Secondly, binding experiments were carried out to establish the effect of one or more histidine residues within a peptide sequence on the affinity of a peptide for these Cu(II)–tacn derived binuclear complexes when immobilized onto a chromatographic support material. The results confirm that for all chelating systems, higher affinity is achieved as the histidine number in the peptide structure increases, although the relative location of the histidine residues in these small peptides did not introduce a significant constraint to the conformation on interacting with the immobilized Cu(II) binuclear complexes.

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Abbreviations

Ac2O:

Acetic anhydride

AMBER:

Assisted model building using energy refinement

DIEA:

Diisopropylethylamine

DMF:

N,N-Dimethylformamide

Et3N:

Triethylamine

Fmoc:

9-Fluorenylmethoxycarbonyl

HBTU:

o-Benzotriazole-N,N,N′,N′-tetramethyluronium hexafluorophosphate

HOBT:

1-Hydroxybenzotriazole

HPLC:

High-performance liquid chromatography

IMAC:

Immobilized metal affinity chromatography

Lbut :

1,4-Bis(1,4,7-triazacyclonon-1-yl)butane

Lmx :

1,3-Bis(1,4,7-triazacyclonon-1-ylmethyl)benzene

Lox :

1,2-Bis(1,4,7-triazacyclonon-1-ylmethyl)benzene

Lpx :

1,4-Bis(1,4,7-triazacyclonon-1-ylmethyl)benzene

PIP:

Piperidine

tacn:

1,4,7-Triazacyclononane

TFA:

Trifluoroacetic acid

TNBSA:

1,3,5-Trinitrobenzenesulfonic acid

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Acknowledgements

These investigations were supported by the Australian Research Council.

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Authors and Affiliations

  1. ARC Special Research Center for Green Chemistry, Monash University, Claylon, VIC, 3800, Australia

    Milton T. W. Hearn

  2. School of Chemistry, Monash University, Claylon, VIC , 3800, Australia

    Bim Graham & Leone Spiccia

  3. Anorganisch-Chemisches Institut, University of Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany

    Peter Comba

Authors
  1. Bim Graham
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  2. Peter Comba
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  3. Milton T. W. Hearn
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  4. Leone Spiccia
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Correspondence to Leone Spiccia.

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Graham, B., Comba, P., Hearn, M.T.W. et al. An examination of the binding behavior of histidine-containing peptides with immobilized metal complexes derived from the macrocyclic ligand, 1,4,7-triazacyclononane. J Biol Inorg Chem 12, 11–21 (2007). https://doi.org/10.1007/s00775-006-0160-3

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