Scaffolded amino acids as a close structural mimic of type-3 copper binding sites

doi:10.1039/b709400k

PMID: 18361361DOI: 10.1039/b709400kMar 26, 2008

Scaffolded amino acids as a close structural mimic of type-3 copper binding sites

Chemical Communications : Chem Comm

H Bauke AlbadaRob M J Liskamp

Abstract

We report the use of triazacyclophane (TAC)-scaffolded amino acids as a structural mimic for 3-histidine metal-binding sites in metalloproteins, especially for the mimicry of type-3 copper binding sites as are present in hemocyanin, tyrosinase and catechol oxidase.

References

Reversible cleavage and formation of the dioxygen O-O bond within a dicopper complex

Mar 8, 1996·Science·J A HalfenW B Tolman

Crystal structure of a plant catechol oxidase containing a dicopper center

Dec 10, 1998·Nature Structural Biology·T KlabundeB Krebs

Enzyme mimics complexing Cu(II) ion: structure-function relationships

Dec 22, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·A CorazzaM Scarpa

A selectively deprotectable triazacyclophane scaffold for the construction of artificial receptors

Oct 27, 2001·Organic Letters·T Opatz, Rob M J Liskamp

Synthesis and screening of libraries of synthetic tripodal receptor molecules with three different amino acid or peptide arms: identification of iron binders

Jul 9, 2002·Journal of Combinatorial Chemistry·Till Opatz, Rob M J Liskamp

Resonance raman investigation of equatorial ligand donor effects on the Cu(2)O(2)(2+) core in end-on and side-on mu-peroxo-dicopper(II) and bis-mu-oxo-dicopper(III) complexes

Apr 24, 2003·Journal of the American Chemical Society·Mark J HensonEdward I Solomon

Structure and spectroscopy of copper-dioxygen complexes

Feb 12, 2004·Chemical Reviews·Liviu M MiricaT Daniel P Stack

Bis(mu-oxo)dicopper(III) complexes of a homologous series of simple peralkylated 1,2-diamines: steric modulation of structure, stability, and reactivity

Oct 11, 2005·Inorganic Chemistry·Adam P ColeT Daniel P Stack

Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis

Jan 27, 2006·The Journal of Biological Chemistry·Yasuyuki MatobaMasanori Sugiyama

New insights into the coordination chemistry and molecular structure of copper(II) histidine complexes in aqueous solutions

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Zeolite framework stabilized copper complex inspired by the 2-His-1-carboxylate facial triad motif yielding oxidation catalysts

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Synthetic models of the active site of catechol oxidase: mechanistic studies

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Citations

Trivalent ultrashort lipopeptides are potent pH dependent antifungal agents

Jan 17, 2012·Journal of Medicinal Chemistry·Christopher J ArnuschYechiel Shai

Nucleoapzymes: Hemin/G-Quadruplex DNAzyme-Aptamer Binding Site Conjugates with Superior Enzyme-like Catalytic Functions

Dec 15, 2015·Journal of the American Chemical Society·Eyal GolubItamar Willner

Biocompatible Supramolecular Catalytic One-Dimensional Nanofibers for Efficient Labeling of Live Cells

Oct 13, 2015·Bioconjugate Chemistry·Mohammad Aref KhalilyMustafa O Guler

Copper(ii) complexes of macrocyclic and open-chain pseudopeptidic ligands: synthesis, characterization and interaction with dicarboxylates

Jun 19, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Enrico FaggiIgnacio Alfonso

Superoxide dismutase mimicking Cu(II)-mixed amino acid complexes covalently grafted onto silica gel--an FT-IR study

Jan 19, 2010·Analytical and Bioanalytical Chemistry·Zita CsendesIstván Pálinkó

A general approach for the non-stop solid phase synthesis of TAC-scaffolded loops towards protein mimics containing discontinuous epitopes

Mar 27, 2009·Chemical Communications : Chem Comm·Cristina ChamorroRob M J Liskamp

Triazacyclophane (TAC)-scaffolded histidine and aspartic acid residues as mimics of non-heme metalloenzyme active sites

Dec 20, 2011·Organic & Biomolecular Chemistry·H Bauke AlbadaRob M J Liskamp

Rational design of supramolecular hemin/G-quadruplex-dopamine aptamer nucleoapzyme systems with superior catalytic performance

May 1, 2016·Chemical Science·H Bauke AlbadaItamar Willner

Related Concepts

Copper

Catechol Oxidase

Hemocyanin

Histidine

Indicators

Metalloproteins

Dioxygen

Infrared Spectrophotometry

Spectrophotometry, Ultraviolet

Raman Optical Activity Spectroscopy

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Scaffolded amino acids as a close structural mimic of type-3 copper binding sites

Abstract

References

Reversible cleavage and formation of the dioxygen O-O bond within a dicopper complex

Crystal structure of a plant catechol oxidase containing a dicopper center

Enzyme mimics complexing Cu(II) ion: structure-function relationships

A selectively deprotectable triazacyclophane scaffold for the construction of artificial receptors

Synthesis and screening of libraries of synthetic tripodal receptor molecules with three different amino acid or peptide arms: identification of iron binders

Resonance raman investigation of equatorial ligand donor effects on the Cu(2)O(2)(2+) core in end-on and side-on mu-peroxo-dicopper(II) and bis-mu-oxo-dicopper(III) complexes

Structure and spectroscopy of copper-dioxygen complexes

Bis(mu-oxo)dicopper(III) complexes of a homologous series of simple peralkylated 1,2-diamines: steric modulation of structure, stability, and reactivity

Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis

New insights into the coordination chemistry and molecular structure of copper(II) histidine complexes in aqueous solutions

Zeolite framework stabilized copper complex inspired by the 2-His-1-carboxylate facial triad motif yielding oxidation catalysts

Synthetic models of the active site of catechol oxidase: mechanistic studies

Modeling the 2-His-1-carboxylate facial triad: iron-catecholato complexes as structural and functional models of the extradiol cleaving dioxygenases

Citations

Trivalent ultrashort lipopeptides are potent pH dependent antifungal agents

Nucleoapzymes: Hemin/G-Quadruplex DNAzyme-Aptamer Binding Site Conjugates with Superior Enzyme-like Catalytic Functions

Biocompatible Supramolecular Catalytic One-Dimensional Nanofibers for Efficient Labeling of Live Cells

Copper(ii) complexes of macrocyclic and open-chain pseudopeptidic ligands: synthesis, characterization and interaction with dicarboxylates

Superoxide dismutase mimicking Cu(II)-mixed amino acid complexes covalently grafted onto silica gel--an FT-IR study

A general approach for the non-stop solid phase synthesis of TAC-scaffolded loops towards protein mimics containing discontinuous epitopes

Triazacyclophane (TAC)-scaffolded histidine and aspartic acid residues as mimics of non-heme metalloenzyme active sites

Rational design of supramolecular hemin/G-quadruplex-dopamine aptamer nucleoapzyme systems with superior catalytic performance

Related Concepts

Related Feeds

Autoimmune Diseases

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