Peptide‐Based Carbohydrate Receptors
Identifieur interne : 001D93 ( Main/Exploration ); précédent : 001D92; suivant : 001D94Peptide‐Based Carbohydrate Receptors
Auteurs : Melanie Rauschenberg [Allemagne] ; Sateesh Bandaru [Allemagne] ; Mark P. Waller [Allemagne] ; Bart Jan Ravoo [Allemagne]Source :
- Chemistry – A European Journal [ 0947-6539 ] ; 2014-03-03.
Abstract
A broad spectrum of physiological processes is mediated by highly specific noncovalent interactions of carbohydrates and proteins. In a recent communication we identified several cyclic hexapeptides in a dynamic combinatorial library that interact selectively with carbohydrates with high binding constants in water. Herein, we report a detailed investigation of the noncovalent interaction of two cyclic hexapeptides (Cys‐His‐Cys (which we call HisHis) and Cys‐Tyr‐Cys (which we call TyrTyr)) with a selection of monosaccharides and disaccharides in aqueous solution. The parallel and antiparallel isomers of HisHis or TyrTyr were synthesized separately, and their interaction with monosaccharides and disaccharides in aqueous solution was studied by isothermal titration calorimetry, NMR spectroscopic titrations, and circular dichroism spectroscopy. From these measurements, we identified particularly stable complexes (Ka>1000 M−1) of the parallel isomer of HisHis with N‐acetylneuraminic acid and with methyl‐α‐D‐galactopyranoside as well as of both isomers of TyrTyr with trehalose. To gain further insight into the structure of the peptide–carbohydrate complexes, structure prediction was performed using quantum chemical methods. The calculations confirm the selectivity observed in the experiments and indicate the formation of multiple intermolecular hydrogen bonds in the most stable complexes.
Peptide talk: Cyclic peptides (see figure) are potent and selective receptors for carbohydrates in aqueous solution. A detailed investigation of the noncovalent interaction of two cyclic hexapeptides with a selection of monosaccharides and disaccharides in aqueous solution is described.
Url:
DOI: 10.1002/chem.201303777
Affiliations:
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Waller</name><affiliation wicri:level="1"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Organic Chemistry Institute, Westfälische Wilhelms‐Universität Münster, Corrensstrasse 40</wicri:regionArea><wicri:noRegion>Corrensstrasse 40</wicri:noRegion><wicri:noRegion>Corrensstrasse 40</wicri:noRegion></affiliation></author><author><name sortKey="Ravoo, Bart Jan" sort="Ravoo, Bart Jan" uniqKey="Ravoo B" first="Bart Jan" last="Ravoo">Bart Jan Ravoo</name><affiliation wicri:level="1"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Organic Chemistry Institute, Westfälische Wilhelms‐Universität Münster, Corrensstrasse 40</wicri:regionArea><wicri:noRegion>Corrensstrasse 40</wicri:noRegion><wicri:noRegion>Corrensstrasse 40</wicri:noRegion></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Allemagne</country></affiliation><affiliation wicri:level="1"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Correspondence address: Organic Chemistry Institute, Westfälische Wilhelms‐Universität Münster, Corrensstrasse 40</wicri:regionArea><wicri:noRegion>Corrensstrasse 40</wicri:noRegion><wicri:noRegion>Corrensstrasse 40</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Chemistry – A European Journal</title><title level="j" type="alt">CHEMISTRY - A EUROPEAN JOURNAL</title><idno type="ISSN">0947-6539</idno><idno type="eISSN">1521-3765</idno><imprint><biblScope unit="vol">20</biblScope><biblScope unit="issue">10</biblScope><biblScope unit="page" from="2770">2770</biblScope><biblScope unit="page" to="2782">2782</biblScope><biblScope unit="page-count">13</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2014-03-03">2014-03-03</date></imprint><idno type="ISSN">0947-6539</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0947-6539</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A broad spectrum of physiological processes is mediated by highly specific noncovalent interactions of carbohydrates and proteins. In a recent communication we identified several cyclic hexapeptides in a dynamic combinatorial library that interact selectively with carbohydrates with high binding constants in water. Herein, we report a detailed investigation of the noncovalent interaction of two cyclic hexapeptides (Cys‐His‐Cys (which we call HisHis) and Cys‐Tyr‐Cys (which we call TyrTyr)) with a selection of monosaccharides and disaccharides in aqueous solution. The parallel and antiparallel isomers of HisHis or TyrTyr were synthesized separately, and their interaction with monosaccharides and disaccharides in aqueous solution was studied by isothermal titration calorimetry, NMR spectroscopic titrations, and circular dichroism spectroscopy. From these measurements, we identified particularly stable complexes (Ka>1000 M−1) of the parallel isomer of HisHis with N‐acetylneuraminic acid and with methyl‐α‐D‐galactopyranoside as well as of both isomers of TyrTyr with trehalose. To gain further insight into the structure of the peptide–carbohydrate complexes, structure prediction was performed using quantum chemical methods. The calculations confirm the selectivity observed in the experiments and indicate the formation of multiple intermolecular hydrogen bonds in the most stable complexes.</div><div type="abstract" xml:lang="en">Peptide talk: Cyclic peptides (see figure) are potent and selective receptors for carbohydrates in aqueous solution. A detailed investigation of the noncovalent interaction of two cyclic hexapeptides with a selection of monosaccharides and disaccharides in aqueous solution is described.</div></front></TEI><affiliations><list><country><li>Allemagne</li></country></list><tree><country name="Allemagne"><noRegion><name sortKey="Rauschenberg, Melanie" sort="Rauschenberg, Melanie" uniqKey="Rauschenberg M" first="Melanie" last="Rauschenberg">Melanie Rauschenberg</name></noRegion><name sortKey="Bandaru, Sateesh" sort="Bandaru, Sateesh" uniqKey="Bandaru S" first="Sateesh" last="Bandaru">Sateesh Bandaru</name><name sortKey="Ravoo, Bart Jan" sort="Ravoo, Bart Jan" uniqKey="Ravoo B" first="Bart Jan" last="Ravoo">Bart Jan Ravoo</name><name sortKey="Ravoo, Bart Jan" sort="Ravoo, Bart Jan" uniqKey="Ravoo B" first="Bart Jan" last="Ravoo">Bart Jan Ravoo</name><name sortKey="Ravoo, Bart Jan" sort="Ravoo, Bart Jan" uniqKey="Ravoo B" first="Bart Jan" last="Ravoo">Bart Jan Ravoo</name><name sortKey="Waller, Mark P" sort="Waller, Mark P" uniqKey="Waller M" first="Mark P." last="Waller">Mark P. 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