Patent number: 8288132
Abstract: The present invention discloses a chemoenzymatic process for the preparation of an iminocyclitol corresponding to formula (I), (II), (III) or (IV), wherein: R1 and R2 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; R3 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: 0 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 R3—CHO, wherein R3 is as defined above.
Type:
Grant
Filed:
August 30, 2007
Date of Patent:
October 16, 2012
Assignees:
Consejo Superior de Investigaciones Cientificas, Bioglane, S.L.N.E.
Inventors:
Pere Clapés Saborit, Jesús Joglar Tamargo, José Antonio Castillo Expósito, Carles Lozano Pérez
Publication number: 20100009417
Abstract: The present invention discloses a chemoenzymatic process for the preparation of an iminocyclitol corresponding to formula (I), (II), (III) or (IV), wherein: R1 and R2 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; R3 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: 0 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 R3—CHO, wherein R3 is as defined above.
Type:
Application
Filed:
August 30, 2007
Publication date:
January 14, 2010
Applicants:
CONSEJO SUPERIOR DE INVESTIGACIONES CIENTÍFICAS, BIOGLANE, S.L.N.E.
Inventors:
Pere Clapés Saborit, Jusús Joglar Tamargo, José Antonio Castillo Expósito, Carles Lozano Pérez