Biomimetic zinc funnel complexes based on Calix[6]N3ArO ligands: An acid-base switch for guest binding

Journal of the American Chemical Society

Volumn 127, Issue 42, 2005, Pages 14833-14840

  Sénèque, Olivier ^a,e   Rager, Marie Noëlle ^b   Giorgi, Michel ^c   Prangé, Thierry ^d   Tomas, Alain ^d   Reinaud, Olivia ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b PSL RESEARCH UNIVERSITY   (France)

^c AIX MARSEILLE UNIVERSITY   (France)

^d UNIVERSITÉ PARIS DESCARTES   (France)

^e UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; AMINO ACIDS; BIOMIMETIC MATERIALS; ENZYMES; PHENOLS;

AMINO PHENOL MOEITY; COORDINATION CHEMISTRY; IMIDAZOLES; LEWIS ACIDITY;

ZINC;

ASTACIN; CALIX[6]ARENE DERIVATIVE; CALIXARENE; IMIDAZOLE DERIVATIVE; LEWIS ACID; LIGAND; PHENOL DERIVATIVE; SERRALISIN; UNCLASSIFIED DRUG; ZINC DERIVATIVE; ZINC PEPTIDASE;

ACID BASE BALANCE; ANION TRANSPORT; ARTICLE; BINDING AFFINITY; BINDING KINETICS; CATION TRANSPORT; COMPLEX FORMATION; ENZYME BINDING; LIGAND BINDING; METAL BINDING;

ACID-BASE EQUILIBRIUM; BIOMIMETICS; CALIXARENES; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, AROMATIC; IMIDAZOLES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHENOLS; REFERENCE STANDARDS; STEREOISOMERISM; ZINC;

EID: 27144474903     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053620e     Document Type: Article

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32. Finally, in our proposed catalytic cycle, inactivation of the enzyme at low pH could stem from the protonation of the glutamate residue.
33. Such a mechanism cannot be efficient in our calixarene-based system as the narrow rim of the macrocycle precludes the stabilization of a tetrahedral intermediate in the endo-position for sterical reasons.
34. 2] = 0.2124. See Table S1 in the Supporting Information.