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Closed Access item Synthesis and Biological Evaluation of Guanidine-Type Iminosugars

Authors:Aguilar Moncayo, Matilde
Díaz Pérez, Paula
García Moreno, María Isabel
Ortiz-Mellet, Carmen
García-Fernández, José Manuel
Keywords:Guanidine, Imino sugars, Magnetic resonance Spectroscopy, Spectrometry
Issue Date:24-Jan-2008
Publisher:American Chemical Society
Citation:Journal of Organic Chemistry 73(5): 1995-1998 (2008)
Abstract:The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported.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.
Description:4 páginas, 1 tabla, 5 esquemas.
Publisher version (URL):http://dx.doi.org/10.1021/jo702374f
Appears in Collections:(IIQ) Artículos

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