| Active transport of amino acids by a guanidiniocarbonyl-pyrrole receptor. | |
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MedLine Citation:
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PMID: 20480464 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Herein we report the synthesis and characterization of a transporter 9 for N-acetylated amino acids. Transporter 9 is a conjugate of a guanidiniocarbonyl pyrrole cation, one of the most efficient carboxylate binding motifs reported so far, and a hydrophobic tris(dodecylbenzyl) group, which ensures solubility in organic solvents. In its protonated form, 9 binds N-acetylated amino acid carboxylates in wet organic solvents with association constants in the range of 10(4) M(-1) as estimated by extraction experiments. Aromatic amino acids are preferred due to additional cation-pi-interactions of the amino acid side chain with the guanidiniocarbonyl pyrrole moiety. U-tube experiments established efficient transport across a bulk liquid chloroform phase with fluxes approaching 10(-6) mol m(-2) s(-1). In experiments with single substrates, the release rate of the amino acid from the receptor-substrate complex at the interface with the receiving phase is rate determining. In contrast to this, in competition experiments with several substrates, the thermodynamic affinity to 9 becomes decisive. As 9 can only transport anions in its protonated form and has a pK(a) value of approximately 7, pH-driven active transport of amino acids is also possible. Transport occurs as a symport of the amino acid carboxylate and a proton. |
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Authors:
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Christian Urban; Carsten Schmuck |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 16 ISSN: 1521-3765 ISO Abbreviation: Chemistry Publication Date: 2010 Aug |
Date Detail:
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Created Date: 2010-08-30 Completed Date: 2010-11-26 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 9502-10 Citation Subset: IM |
Affiliation:
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Universität Duisburg-Essen, Institut für Organische Chemie, Universitätsstrasse 7, 45141 Essen, Germany. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry,
metabolism* Anions / chemistry, metabolism Binding Sites Biological Transport, Active / physiology* Cations / chemistry, metabolism* Guanidine / chemistry, metabolism* Molecular Structure Pyrroles / chemistry, metabolism* Solvents / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Anions; 0/Cations; 0/Pyrroles; 0/Solvents; 113-00-8/Guanidine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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