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NMR spectroscopy and isothermal titration calorimetry binding measurements showed that cleavage of one pillar of the cage was beneficial to the binding properties of the receptor, as long as two residual amino groups of the cleaved pillar were present. Removal of these two residual amino groups produced a dramatic loss of affinity for Oct\u03b2Glc of the resulting monocyclic analogue of the parent cage receptor. A significant improvement in the binding ability was achieved by replacing one pillar with two aminopyrrolic hydrogen\u2010bonding arms, despite the loss of a preorganized structure. In contrast to the cage receptor, recognition of Oct\u03b2Glc was observed, even in a competitive medium (30\u2009% DMF in chloroform). Structural studies in solution, carried out through NMR spectroscopy and molecular modeling calculations, led to the elucidation of the 3D binding modes of the side\u2010armed monocyclic receptors; this highlighted the key role of the amino groups and demonstrated the occurrence of a rotaxane\u2010like complex, which featured the octyl chain of the glucoside threaded through the macrocyclic ring.<\/jats:p>","DOI":"10.1002\/chem.201400365","type":"journal-article","created":{"date-parts":[[2014,4,3]],"date-time":"2014-04-03T12:36:38Z","timestamp":1396528598000},"page":"6081-6091","source":"Crossref","is-referenced-by-count":42,"title":["Systematic Dissection of an Aminopyrrolic Cage Receptor for \u03b2\u2010Glucopyranosides Reveals the Essentials for Effective Recognition"],"prefix":"10.1002","volume":"20","author":[{"given":"Oscar","family":"Francesconi","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matteo","family":"Gentili","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cristina","family":"Nativi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana","family":"Ard\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"F. 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