title: Water-Soluble Cavitands: Synthesis of Methylene-Bridged Resorcin[4]arenes Containing Hydroxyls and Phosphates at Their Feet and Bromomethyls and Thiomethyls at Their Rims.
abstract: The synthesis of rim-functionalized methylene-bridged resorcin[4]arenes ("cavitands") containing hydrophilic propanol or water-solublilizing propylphosphate feet is described. The cavitands possess the synthetically useful benzylthiol (cavitands 6 and 16) or benzylbromide (cavitands 9 and 11) functionalities at their rims, which are suitable for further derivatization near the hydrophobic cavity of the cavitand. These water-soluble cavitands represent new building blocks that are ideal for use in aqueous supramolecular chemistry. As an example of their synthetic utility in supramolecular studies, we have reacted phosphate-footed cavitands 11 and 16 with cysteine-containing peptide 17 and chloroacetylated peptide 19, respectively, to afford the corresponding de novo proteins 18 and 20.
authors.affiliation: Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada, V6T 1Z1.
authors.forename: Adam R.
authors.initials: AR
authors.lastname: Mezo
authors.forename: John C.
authors.initials: JC
authors.lastname: Sherman