CHEMOENZYMATIC PROCESS FOR THE PREPARATION OF IMINOCYCLITOLS

• Main Authors: CLAPES SABORIT PERE, LOZANO PEREZ CARLES, CASTILLO EXPOSITO JOSE ANTONIO, JOGLAR TAMARGO JESUS
• Format: Patent
• Language: English; Spanish
• Published: 01.05.2008
• Subjects: BEER; BIOCHEMISTRY; CHEMISTRY; ENZYMOLOGY; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; SPIRITS; VINEGAR; WINE

The present invention discloses a chemoenzymatic process for the preparation of an iminocyclitol corresponding to formula (I), (II), (III) or (IV), wherein: R and R are the same or different, and independently selected from the group consisting of: H, OH, hydroxymethyl, methyl, ethyl, butyl, pentyl, hexyl, octyl, isopropyl, isobutyl, 2-methylbutyl, and benzyl R is selected from the group consisting of: H, hydroxymethyl, hydroxyethyl, ethyl, butyl, pentyl, hexyl, octyl, dodecyl, isobutyl, isopropyl, isopentyl, 2- methylbutyl, benzyl, and phenylethyl n: O or 1 the process comprising: (i) an aldol addition catalyzed by a D-fructose-6-phosphate aldolase enzyme (FSA) and an acceptor aminoaldehyde and (ii) an intramolecular reductive amination of the addition adduct obtained in step (i) with H2, in the presence of a metallic catalyst, optionally being carried out said step (ii) in the presence of an aldehyde of formula R -CHO, wherein R is as defined above. Procedimiento quimo-enzimático para la síntesis de iminociclitoles e iminociclitoles así obtenidos. La presente invención describe un procedimiento quimo-enzimático útil para la síntesis de iminociclitoles basado en la utilización de la enzima D-fructosa-6-fosfato aldolasa (FSA), como por ejemplo: D-fagomina, 1-deoxinojirimicina y derivados N-sustituidos. Estos iminociclitoles, así obtenidos, pueden ser inhibidores de glicosiltransferasas y glicosidasas y pueden ser, por tanto, útiles para la elaboración de composiciones farmacéuticas para el tratamiento de enfermedades humanas.