An Octa‐Urea [Pd2L4]4+ Cage that Selectively Binds to n‐octyl‐α‐D‐Mannoside. Issue 12 (19th May 2021)

• Record Type: Journal Article
• Authors: Schaapkens, Xander; Holdener, Joël H.; Tolboom, Jens; Bobylev, Eduard O.; Reek, Joost N. H.; Mooibroek, Tiddo J.
• Is Part Of: Chemphyschem. Volume 22:Issue 12(2021)
• Page Start: 1187
• Page End: 1192
• Publication Date: 2021-05-19
• Subjects: molecular recognition -- carbohydrates -- cage compounds -- supramolecular chemistry -- coordination compound; Chemistry, Physical and theoretical -- Periodicals; 541.05
• DOI: 10.1002/cphc.202100229
• Languages: English
• ISSNs: 1439-4235

Abstract

Abstract: Designing compounds for the selective molecular recognition of carbohydrates is a challenging task for supramolecular chemists. Macrocyclic compounds that incorporate isophtalamide or bisurea spacers linking two aromatic moieties have proven effective for the selective recognition of all‐equatorial carbohydrates. Here, we explore the molecular recognition properties of an octa‐urea [Pd2 L4 ] 4+ cage complex (4 ). It was found that small anions like NO3 − and BF4 − bind inside 4 and inhibit binding of n ‐octyl glycosides. When the large non‐coordinating anion 'BAr F ' was used, 4 showed excellent selectivity towards n ‐octyl‐α‐D‐Mannoside with binding in the order of K a ≈16 M −1 versus non‐measurable affinities for other glycosides including n ‐octyl‐β‐D‐Glucoside (in CH3 CN/H2 O 91 : 9). Abstract : An octa‐urea [Pd2 L4 ] 4+ cage complex with non‐coordinating BAr F counter ions selectively binds to n ‐Oct‐α‐D‐Mannoside with K a =16 M −1 in CH3 CN/H2 O (91 : 9). Other carbohydrates such as n ‐Oct‐β‐D‐Glucoside do not bind in this competitive matrix.