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Association constants showed to be unfavorably affected by increasing steric hindrance of the side chain. Quite surprisingly, different association constants were measured for the <jats:sc>L<\/jats:sc> and <jats:sc>D<\/jats:sc> enantiomers. These data suggest that aminoacids are bound via two interactions, zinc\u2010carboxylate coordination and two hydrogen bonds between the ammonium group of the aminoacid and two oxygen atoms of one <jats:sc>D<\/jats:sc>\u2010glucose moiety. Such conclusion is supported by the result of semiempirical (PM3) calculations. Notably, the <jats:italic>K<\/jats:italic><jats:sub>L<\/jats:sub>\/<jats:italic>K<\/jats:italic><jats:sub>D<\/jats:sub> value of 9.6 observed for the association of phenylalanine rivals with the highest values found for the chiral recognition of aminoacids in water. Chirality, 2009. \u00a9 2008 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/chir.20614","type":"journal-article","created":{"date-parts":[[2008,7,24]],"date-time":"2008-07-24T19:43:13Z","timestamp":1216928593000},"page":"104-109","source":"Crossref","is-referenced-by-count":33,"title":["A new water soluble Zn\u2010salophen derivative as a receptor for \u03b1\u2010aminoacids: Unexpected chiral discrimination"],"prefix":"10.1002","volume":"21","author":[{"given":"Antonella","family":"Dalla Cort","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paolo","family":"De Bernardin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luca","family":"Schiaffino","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2008,7,24]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)02654-9"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)01687-7"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/b514896k"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0356340"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0302837"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.12.120"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/B307853C"},{"key":"e_1_2_1_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702680"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/b700723j"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/b702375h"},{"key":"e_1_2_1_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200500227"},{"key":"e_1_2_1_13_2","doi-asserted-by":"publisher","DOI":"10.1038\/258677a0"},{"key":"e_1_2_1_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390256"},{"key":"e_1_2_1_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2006.08.043"},{"key":"e_1_2_1_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)79304-X"},{"key":"e_1_2_1_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(96)00832-0"},{"key":"e_1_2_1_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00103a047"},{"key":"e_1_2_1_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp052408u"},{"key":"e_1_2_1_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/b613705a"},{"key":"e_1_2_1_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2006.11.026"},{"key":"e_1_2_1_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0020-1693(97)06131-8"},{"key":"e_1_2_1_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/b503708e"},{"key":"e_1_2_1_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2006.05.039"},{"key":"e_1_2_1_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic701385m"},{"key":"e_1_2_1_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0206263"},{"key":"e_1_2_1_27_2","unstructured":"Gaussian 03 Revision B.05 FrischMJ TrucksGW SchlegelHB ScuseriaGE RobbMA CheesemanJR MontgomeryJA Jr VrevenT KudinKN BurantJC MillamJM IyengarSS TomasiJ BaroneV MennucciB CossiM ScalmaniG RegaN PeterssonGA NakatsujiH HadaM EharaM ToyotaK FukudaR HasegawaJ IshidaM NakajimaT HondaY KitaoO NakaiH KleneM LiX KnoxJE HratchianHP CrossJB BakkenV AdamoC JaramilloJ GompertsR StratmannRE YazyevO AustinAJ CammiR PomelliC OchterskiJW AyalaPY MorokumaK VothGA SalvadorP DannenbergJJ ZakrzewskiVG DapprichS DanielsAD StrainMC FarkasO MalickDK RabuckAD RaghavachariK ForesmanJB OrtizJV CuiQ BaboulAG CliffordS CioslowskiJ StefanovBB LiuG LiashenkoA PiskorzP KomaromiI MartinRL FoxDJ KeithT Al\u2010LahamMA PengCY NanayakkaraA ChallacombeM GillPMW JohnsonBCW WongMW GonzalezC andPopleJA Gaussian Inc. 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