Chemoenzymatic process for the preparation of iminocyclitols

Details Chemoenzymatic process for the preparation of iminocyclitols Chemoenzymatic process for the preparation of iminocyclitols

C - Chemistry, Metallurgy

12

P

C12P 17/10 (2006.01) C12P 19/26 (2006.01)

Patent

CA 2661772

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: 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 R3-CHO, wherein R3 is as defined above.

L'invention concerne un procédé chimioenzymatique pour la préparation d'un iminocyclitol correspondant à la formule (I), (II), (III) ou (IV), dans laquelle R1 et R2 sont identiques ou différents, et indépendamment choisis dans le groupe formé de: H, OH, hydroxyméthyle, méthyle, éthyle, butyle, pentyle, hexyle, octyle, isopropyle, isobutyle, 2-méthylbutyle, et benzyle; R3 est choisi dans le groupe formé de H, hydroxyméthyle, hydroxyéthyle, éthyle, butyle, pentyle, hexyle, octyle, dodécyle, isobutyle, isopropyle, isopentyle, 2- méthylbutyle, benzyle, et phényléthyle; n étant égal à 0 ou 1; le procédé consistant: (i) en une addition d'aldol catalysée par une enzyme D-fructose-6-phosphate aldolase (FSA) et un aminoaldéhyde accepteur; et (ii) en une amination réductrice intramoléculaire du produit d'addition obtenu en (i) avec H2, en présence d'un catalyseur métallique, l'étape (ii) étant éventuellement réalisée en présence d'un aldéhyde de formule R3-CHO, R3 étant tel que défini ci-dessus.

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