Synthesis of aminocyclodextrin carboxylic acids (6-amino-6¢-carboxylic acid) via selective amination and oxidation of 6 A ,6 D -dihydroxy a-and b-cyclodextrins, respectively, is reported.Keywords: a-and b-cyclodextrin amino acids, azido cyclodextrin carboxylic acids, aminationIn spite of their many interesting molecular properties, the cyclodextrins (CDS) 1 have not been used as sugar-based macrocyclic amino hexuronic acids. 2 The proposed structures of such compounds in the a-and b-CD series are shown in Figure 1. Figure 1 a-and b-CD amino hexuronic acids.Among the many possible applications of such bifunctional amphoteric CDs, one can envisage appending preferred sequences of amino acids to both amino and carboxylic groups to create antiparallel arrays of templated peptidic sequences. 3 Depending on the nature and configuration of the amino acids, such oligopeptides may adopt interesting secondary structures including helical or b-sheet-like shapes. 4 With this ultimate objective in mind, we first set out to address the synthesis of CD bearing single amino and carboxylic acid groups on predetermined D-glucopyranosyl units by appropriate modification of two primary hydroxyl groups on a-and b-CD. We have previously reported on methods of functionalization of the primary and secondary faces of CD, 5 as well as the elaboration of CD-calixarene hybrids. 6
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