title: 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.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland. Electronic address: potopnyk@gmail.com.
authors.forename: Mykhaylo A
authors.initials: MA
authors.lastname: Potopnyk
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland. Electronic address: slawomir.jarosz@icho.edu.pl.
authors.forename: Sławomir
authors.initials: S
authors.lastname: Jarosz
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry; D015195:Drug Design; D004987:Ethers / Q000737:chemistry; D006020:Glycopeptides / Q000737:chemistry; D006031:Glycosylation; D006801:Humans; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D043844:Crown Ethers; D004987:Ethers; D006020:Glycopeptides; D047028:Macrocyclic Compounds; D010455:Peptides; D010456:Peptides, Cyclic; D009584:Nitrogen
keywords: Aza-crown ethers; Complexation; Macrocyclic receptors; Sugars; Synthesis