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Water-soluble cavitands: Synthesis of methylene-bridged resorcin[4]arenes containing hydroxyls and phosphates at their feet and bromomethyls and thiomethyls at their rims

TitleWater-soluble cavitands: Synthesis of methylene-bridged resorcin[4]arenes containing hydroxyls and phosphates at their feet and bromomethyls and thiomethyls at their rims
Publication TypeJournal Article
Year of Publication1998
AuthorsMezo, AR, Sherman, JC
JournalJournal of Organic Chemistry
Volume63
Pagination6824-6829
Date PublishedOct
Type of ArticleArticle
ISBN Number0022-3263
KeywordsADSORPTION, BUILDING-BLOCKS, CARCERANDS, ENCAPSULATION, HOST-GUEST COMPLEXATION, MOLECULAR, PHASE, RECOGNITION, RESORCINARENES, SELF-ASSEMBLED MONOLAYERS
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.

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