{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,31]],"date-time":"2025-12-31T18:34:39Z","timestamp":1767206079594,"version":"build-2238731810"},"reference-count":66,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2022,4,14]],"date-time":"2022-04-14T00:00:00Z","timestamp":1649894400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>\n                    We present the synthesis of new chiral water-soluble dimeric capsules by the multicomponent Mannich reaction between charged amino acids (glutamic acid or arginine), resorcinarene, and formaldehyde and by subsequent self-assembly. The zwitterionic character of the backbones enables electrostatic interactions between arms and induces self-assembly of dimeric capsules, namely, (L-\n                    <jats:bold>ArgR<\/jats:bold>\n                    )\n                    <jats:sub>2<\/jats:sub>\n                    and (L-\n                    <jats:bold>GluR<\/jats:bold>\n                    )\n                    <jats:sub>2<\/jats:sub>\n                    , in water with a wide range of pH, as demonstrated by NMR, diffusion coefficient measurement, and circular dichroism. The assembly\/disassembly processes are fast on the NMR timescale. This mode of dimerization leaves side chains available for additional interactions and creates chiral cavities of mixed hydrophobic\/hydrophilic character. According to this characteristic, capsules do not bind fully nonpolar or fully polar guests but effectively encapsulate a variety of chiral molecules with mixed polar\/apolar characters (aliphatic and aromatic aldehydes, epoxides, alcohols, carboxylic acids, amines, and amino acids) with moderate strength. We also demonstrate the formation of heterocapsules (\n                    <jats:bold>GluR<\/jats:bold>\n                    ) (\n                    <jats:bold>ArgR<\/jats:bold>\n                    ) (homo- and heterochiral) that utilize additional interactions between charged acidic and basic side chains and have better encapsulation properties than those of the homodimers.\n                  <\/jats:p>","DOI":"10.3389\/fchem.2022.883093","type":"journal-article","created":{"date-parts":[[2022,4,14]],"date-time":"2022-04-14T06:55:07Z","timestamp":1649919307000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":2,"title":["Chiral Water-Soluble Molecular Capsules With Amphiphilic Interiors"],"prefix":"10.3389","volume":"10","author":[{"given":"Arkadiusz Marek","family":"Sakowicz","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Agnieszka","family":"Szumna","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1965","published-online":{"date-parts":[[2022,4,14]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"3261","DOI":"10.1039\/c2cs35461f","article-title":"Hydrogen-Bonded Supramolecular Capsules with Functionalized Interiors: the Controlled Orientation of Included Guests","volume":"42","author":"Adriaenssens","year":"2013","journal-title":"Chem. 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