title: Recent developments in glycosyl urea synthesis.
abstract: The area of sugar urea derivatives has received considerable attention in recent years because of the unique structural properties and activities that these compounds display. The urea-linkage at the anomeric center is a robust alternative to the naturally occurring O- and N-glycosidic linkages of oligosaccharides and glycoconjugates, and the natural products that have been identified to contain these structures show remarkable biological activity. While methods for installing the β-urea-linkage at the anomeric center have been around for decades, the first synthesis of α-urea glycosides has been much more recent. In either case, the selective synthesis of glycosyl ureas can be quite challenging, and a mixture of α- and β-isomers will often result. This paper will provide a comprehensive review of the synthetic approaches to α- and β-urea glycosides and examine the structure and activity of the natural products and their analogues that have been identified to contain them.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA 52242, United States.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: McKay
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA 52242, United States. Electronic address: hien-nguyen@uiowa.edu.
authors.forename: Hien M
authors.initials: HM
authors.lastname: Nguyen
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis; D006020:Glycopeptides / Q000138:chemical synthesis; D013095:Spermidine / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000617:Aminoglycosides; D006001:Glycoconjugates; D006020:Glycopeptides; D014508:Urea; D005947:Glucose; D013095:Spermidine; C034432:cinodine
keywords: Carbohydrate; Neoglycoconjugate; Pseudooligosaccharide; Rearrangement; Stereoselectivity; Urea