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"snippet" : true } ], "journal" : { "otype" : "Journal", "mtid" : 1062264, "link" : "/api/journal/1062264", "label" : "CHEMISTRY-A EUROPEAN JOURNAL 0947-6539 1521-3765", "pIssn" : "0947-6539", "eIssn" : "1521-3765", "reviewType" : "REVIEWED", "noIF" : false, "sciIndexed" : true, "scopusIndexed" : true, "lang" : "FOREIGN", "hungarian" : false, "published" : true, "oldId" : 1062264, "snippet" : true }, "volume" : "21", "issue" : "16", "firstPage" : "6173", "lastPage" : "6180", "firstPageOrInternalIdForSort" : "6173", "pageLength" : 8, "publishedYear" : 2015, "abstractText" : "The mimicry of protein-sized β-sheet structures with unnatural peptidic sequences (foldamers) is a considerable challenge. In this work, the de novo designed betabellin-14 β-sheet has been used as a template, and α→β residue mutations were carried out in the hydrophobic core (positions 12 and 19). β-Residues with diverse structural properties were utilized: Homologous β3-amino acids, (1R,2S)-2-aminocyclopentanecarboxylic acid (ACPC), (1R,2S)-2-aminocyclohexanecarboxylic acid (ACHC), (1R,2S)-2-aminocyclohex-3-enecarboxylic acid (ACEC), and (1S,2S,3R,5S)-2-amino-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxylic acid (ABHC). Six α/β-peptidic chains were constructed in both monomeric and disulfide-linked dimeric forms. Structural studies based on circular dichroism spectroscopy, the analysis of NMR chemical shifts, and molecular dynamics simulations revealed that dimerization induced β-sheet formation in the 64-residue foldameric systems. Core replacement with (1R,2S)-ACHC was found to be unique among the β-amino acid building blocks studied because it was simultaneously able to maintain the interstrand hydrogen-bonding network and to fit sterically into the hydrophobic interior of the β-sandwich. The novel β-sandwich model containing 25% unnatural building blocks afforded protein-like thermal denaturation behavior. Dissolving sandwiches: A water-soluble β-sandwich has been constructed by using cyclic β-amino acids in the hydrophobic core (see figure). The structural stability is highly dependent on the side-chain, and the destructuring effects of the β-residues could be minimized by using (1R,2S)-2-aminocyclohexanecarboxylic acid. The β-sandwich displays protein-like thermal denaturation behavior.", "subjects" : [ { "otype" : "Classification", "mtid" : 12184, "link" : "/api/classification/12184", "label" : "Farmakológia és gyógyszerészet", "published" : true, "snippet" : true }, { "otype" : "Classification", "mtid" : 10398, "link" : "/api/classification/10398", "label" : "Gyógyszerkémia", "published" : true, "snippet" : true }, { "otype" : "Classification", "mtid" : 10293, "link" : "/api/classification/10293", "label" : "Kémiai tudományok", "published" : true, "snippet" : true }, { "otype" : "Classification", "mtid" : 10299, "link" : "/api/classification/10299", "label" : "Szintetikus szerveskémia", "published" : true, "snippet" : true }, { "otype" : "Classification", "mtid" : 10306, "link" : "/api/classification/10306", "label" : "Sztereokémia", "published" : true, "snippet" : true } ], "keywords" : [ { "otype" : "Keyword", "mtid" : 384, "link" : "/api/keyword/384", "label" : "PROTEINS", "published" : true, 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Unnatural self-organizing biomimetic polymers (foldamers) emerged as promising materials for biomolecule recognition and inhibition. Our goal was to construct multivalent foldamer-dendrimer conjugates which wrap the synaptotoxic β-amyloid (Aβ) oligomers with high affinity through their helical foldamer tentacles. Oligomeric Aβ species play pivotal role in Alzheimer's disease, therefore recognition and direct inhibition of this undruggable target is a great current challenge.
Short helical β-peptide foldamers with designed secondary structures and side chain chemistry patterns were applied as potential recognition segments and their binding to the target was tested with NMR methods (saturation transfer difference and transferred-nuclear Overhauser effect). Helices exhibiting binding in the µM region were coupled to a tetravalent G0-PAMAM dendrimer.
The combination of the foldamer methodology, the fragment-based approach and the multivalent design offers a pathway to unnatural protein mimetics that are capable of specific molecular recognition, and has already resulted in an inhibitor for an extremely difficult target.