title: Synthesis and biological evaluation of guanidine-type iminosugars.
abstract: The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose --> piperidine rearrangement of 5-deoxy-5-guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.
authors.affiliation: Departamento de Química OrgAnica, Facultad de Química, Universidad de Sevilla, Profesor García GonzAlez 1, E-41012 Sevilla, Spain.
authors.forename: Matilde
authors.initials: M
authors.lastname: Aguilar
authors.forename: Paula
authors.initials: P
authors.lastname: Díaz-Pérez
authors.forename: M Isabel
authors.initials: MI
authors.lastname: García-Moreno
authors.forename: Carmen Ortiz
authors.initials: CO
authors.lastname: Mellet
authors.forename: José M
authors.initials: JM
authors.lastname: García Fernandez
mesh_terms: D004353:Drug Evaluation, Preclinical; D019791:Guanidine / Q000138:chemical synthesis* / Q000494:pharmacology*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment
chemical_list: D050111:Imino Sugars; D019791:Guanidine