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Poznik, Michal ; König, Burkhard

Cooperative hydrolysis of aryl esters on functionalized membrane surfaces and in micellar solutions

Poznik, Michal und König, Burkhard (2014) Cooperative hydrolysis of aryl esters on functionalized membrane surfaces and in micellar solutions. Organic & Biomolecular Chemistry 12, S. 3175-3180.

Veröffentlichungsdatum dieses Volltextes: 21 Apr 2015 06:23
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.29820


Zusammenfassung

Catalytic hydrolysis of peptides, proteins, phosphates or carboxylate esters in nature is catalysed by enzymes, which are efficient, fast and selective. Most of the hydrolytic chemical catalysts published so far mimic the active site of enzymes and contain metal complexes and amino acid residues. Their synthesis can be laborious, while the hydrolytic activity is still limited compared to enzymes. ...

Catalytic hydrolysis of peptides, proteins, phosphates or carboxylate esters in nature is catalysed by enzymes, which are efficient, fast and selective. Most of the hydrolytic chemical catalysts published so far mimic the active site of enzymes and contain metal complexes and amino acid residues. Their synthesis can be laborious, while the hydrolytic activity is still limited compared to enzymes. We present an approach that uses fluid membranes of vesicles and micelles as a support for amphiphilic additives, which cooperatively cleave aryl ester bonds. The membrane anchored bis-Zn(II)-complex 1 is hydrolytically active and hydrolyses fluorescein diacetate (FDA) with a second order rate constant (k(2)) of 0.9 M-1 s(-1). The hydrolytic activity is modulated by co-embedded membrane additives, bearing common amino acid side chain functional groups. With this approach, the hydrolytic activity of the system is enhanced up to 16 fold in comparison with cyclen 1 (k(2) = 14.7 M-1 s(-1)). DOPC and DSPC lipids form at room temperature fluid or gel phase membranes, respectively. Omitting the lipid, micellar solutions were obtained with hydrolytic activity reaching k(2) = 13.4 M-1 s(-1). It is shown that cooperative hydrolysis is favoured in fluid membranes and micelles, allowing the active moieties to arrange freely. The embedding and dynamic self-assembly of membrane active components in fluid membranes and micelles provide facile access to hydrolytically active soft interfaces.



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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftOrganic & Biomolecular Chemistry
Verlag:ROYAL SOC CHEMISTRY
Ort der Veröffentlichung:CAMBRIDGE
Band:12
Seitenbereich:S. 3175-3180
Datum2014
Zusätzliche Informationen (Öffentlich)Open-Access-Komponente aus der Allianzlizenz
InstitutionenChemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identifikationsnummer
WertTyp
10.1039/c4ob00247dDOI
Stichwörter / Keywords1,4,7,10-TETRAAZACYCLODODECANE METAL-COMPLEXES; POTENT PROMOTERS; PHYSIOLOGICAL CONDITIONS; ACID ESTERS; ACCELERATION; VESICLES; METALLOMICELLES; METALLOENZYMES; SURFACTANTS; CATALYSIS;
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-298201
Dokumenten-ID29820

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