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Titolo:
Receptor properties of cyclic peptides composed of alternating natural amino acids and 3-aminobenzoic acid derivatives
Autore:
Kubik, S; Bitta, J; Goddard, R; Kubik, D; Pohl, S;
Indirizzi:
Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany Univ Dusseldorf Dusseldorf Germany D-40225 , D-40225 Dusseldorf, Germany Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany Max Planck Inst Kohlenforsch Mulheim Germany D-45470 70 Mulheim, Germany
Titolo Testata:
MATERIALS SCIENCE & ENGINEERING C-BIOMIMETIC AND SUPRAMOLECULAR SYSTEMS
fascicolo: 1-2, volume: 18, anno: 2001,
pagine: 125 - 133
SICI:
0928-4931(200112)18:1-2<125:RPOCPC>2.0.ZU;2-J
Fonte:
ISI
Lingua:
ENG
Soggetto:
CATION-PI INTERACTIONS; QUATERNARY AMMONIUM-IONS; HIGH-AFFINITY LIGANDS; MOLECULAR RECOGNITION; COMPLEXATION; TEMPLATE; CALIXARENES; BINDING; SIZE; HOMOOXACALIXARENES;
Keywords:
cyclopeptides; artificial receptors; cation-pi interactions; conformation analysis; carbohydrate recognition;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
52
Recensione:
Indirizzi per estratti:
Indirizzo: Kubik, S Univ Dusseldorf, Inst Organ Chem & Makromol Chem, Univ Str 1, D-40225 Dusseldorf, Germany Univ Dusseldorf Univ Str 1 Dusseldorf Germany D-40225 f, Germany
Citazione:
S. Kubik et al., "Receptor properties of cyclic peptides composed of alternating natural amino acids and 3-aminobenzoic acid derivatives", MAT SCI E C, 18(1-2), 2001, pp. 125-133

Abstract

Our investigations into the receptor properties of cyclic hexapeptides composed of alternating natural amino acids and 3-aminobenzoic acids are presented. Peptides of this type bind cations such as quaternary ammonium ions by cation-pi interactions with the aromatic subunits. Anions can be bound, but only when they are able to form hydrogen bonds to the peptide NH groups. Anion complexation causes a receptor preorganization and results in a drastic increase in cation complex stability. In the absence of anions that bind to the NH groups, the solution conformation and consequently also the receptor properties of the peptides are sensitive to the nature of the subunits from which they are composed. A cyclic peptide with proline subunits, e.g., forms more stable cation complexes than a more flexible peptide with glutamic acid subunits. Conformational control can alternatively be achieved by introducing substituents in the 4-position of the aromatic subunits of the proline containing peptide. By varying these substituents, systematically, receptors are accessible whose cation complex stabilities range between ca. 100 and 10,000 M-1 in CDCl3. Interestingly, substituents other than H completely eliminate the anion affinity of the corresponding macrocycles. Residues in the 5-position of the aromatic subunits have no influence on peptide conformation. They can be used as binding sites for guest molecules, andpeptide derivatives carrying substituents with free carboxylate groups at the 5-position of the aromatic subunits bind monosaccharides in chloroform. (C) 2001 Elsevier Science B.V. All rights reserved.

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Documento generato il 23/01/20 alle ore 06:53:40