Nitrogen-containing macrocycles having a carbohydrate scaffold.

Abstract

Nitrogen-containing macrocyclic compounds (amines, amides, and N-heterocyclic derivatives) are important targets in supramolecular chemistry. This chapter discusses the importance of aza-macrocycles in general and, in particular, those receptors containing sugar unit(s). The combination of a carbohydrate scaffold bearing nitrogen-containing functional groups in macrocyclic molecules opens a convenient route to chiral receptors having potentially useful properties. The carbohydrate-based macrocycles discussed are classified into several general groups: (1) aza-crown ethers containing a carbohydrate subunit, (2) cyclic homooligomers from amino sugars, (3) sugar-based cryptands, (4) cyclic peptides containing amino sugar units (including C2- and C3-symmetrical macrocyclic glycopeptides), (5) nitrogen- containing glycophanes, and (6) 1,2,3-triazoles containing synthetic cyclodextrin analogues. The general strategies employed, as well as specific ones leading to such complex derivatives, are surveyed. Applications of such carbohydrate receptors, pointing to their importance as hosts in supramolecular chemistry, are discussed.