title: Carbohydrate-steroid conjugation by Ugi reaction: one-pot synthesis of triple sugar/pseudo-peptide/spirostane hybrids.
abstract: The one-pot synthesis of novel molecular chimeras incorporating sugar, pseudo-peptide, and steroidal moieties is described. For this, a new carbohydrate-steroid conjugation approach based on the Ugi four-component reaction was implemented for the ligation of glucose and chacotriose to spirostanic steroids. The approach proved wide substrate scope, as both mono and oligosaccharides functionalized with amino, carboxy, and isocyano groups were conjugated to steroidal substrates in an efficient, multicomponent manner. Two alternative strategies based on the hydrazoic acid variant of the Ugi reaction were employed for the synthesis of tetrazole-based chacotriose-diosgenin conjugates resembling naturally occurring spirostan saponins. This is the first time that triple sugar/pseudo-peptide/steroid hybrids are produced, thus opening up an avenue of opportunities for applications in drug discovery and biological chemistry.
authors.affiliation: Center for Natural Products Study, Faculty of Chemistry, University of Havana, La Habana, Cuba. dgr@fq.uh.cu
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Rivera
authors.forename: Karell
authors.initials: K
authors.lastname: Pérez-Labrada
authors.forename: Liudmila
authors.initials: L
authors.lastname: Lambert
authors.forename: Simon
authors.initials: S
authors.lastname: Dörner
authors.forename: Bernhard
authors.initials: B
authors.lastname: Westermann
authors.forename: Ludger A
authors.initials: LA
authors.lastname: Wessjohann
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D057786:Peptidomimetics / Q000737:chemistry*; D013150:Spirostans / Q000737:chemistry*; D013777:Tetrazoles / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D057786:Peptidomimetics; D013150:Spirostans; D013777:Tetrazoles