Deracemisation of amines

Chemistry: molecular biology and microbiology – Enzyme – proenzyme; compositions thereof; process for... – Oxidoreductase

Reexamination Certificate

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C435S106000, C435S128000, C435S069100, C536S023200

Reexamination Certificate

active

10508356

ABSTRACT:
The present invention relates to a method for the deracemisation or chiral inversion of chiral amines by enzymatic treatment. The method employs a stereoselective enzymatic conversion and either a non-selective or partially selective chemical or enzymatic conversion, simultaneously or sequentially. The invention also provides a method for selecting a suitable enzyme, particularly a suitable amine oxidase, and for the generation of novel enzymes suitable for use in the deracemisation method.

REFERENCES:
Alexeeva, Marina et al., “Deracemization of alpha-methylbenzylamine using an enzyme obtained by in vitro evolution,”Angewandte Chemie, Sep. 2, 2002, vol. 41, No. 17, pp. 3177-3180.
Beard, Timothy M. et al., “Deracemisation and stereoinversion of alpha-amino acids using D-amino acid oxidase and hydride reducing agents,”Chemical Communications, Feb. 7, 2002, pp. 246-247.
Alexandre, F-R, et al., “Amine-boranes: effective reducing agents for the deracemisation of dl-amino acids using 1-amino acid oxidase from Proteus myxofaciens,”Tetrahedron Letters, vol. 43, No. 4, Jan. 21, 2002, pp. 707-710.
Kroutil, W., et al., “Deracemization of compounds possessing a sec-alcohol or -amino group through a cyclic oxidation-reduction sequence: a kinetic treatment,”Tetrahedron: Asymmetry, vol. 9, No. 16, Aug. 1, 1998, pp. 2901-2913.
Schilling, B. et al., “Amine Oxidases from Aspergillus Niger: Identification of a Novel Flavin-Dependent Enzyme,”Biochimica et Biophysica ACTA, vol. 1243, 1995, pp. 529-537.
Doxtert, P.L., et al., Interactions of Monoamine Oxidase with Substrates and Inhibitors,Medicinal Research Reviews, vol. 9, No. 1, 1989, pp. 45-89.
Schilling, B., et al., “Cloning, Sequncing and Heterologous Expression of the Monoamine Oxidase Gene from Aspergillus Niger,”Mol. Gen. Genet, vol. 247, 1995, pp. 430-438.
Geha, Rani Maurice et al., “Substrate and inhibitor specificities for human monoamine oxidase A and B are influenced by a single amino acid,”Journal of Biological Chemistry, vol. 276, No. 13, Mar. 30, 2001, pp. 9877-9882.
Tsugeno, Yukio et al., “A key amino acid responsible for substrate selectivity of monoamine oxidase A and B,”Journal of Biological Chemistry, vol. 272, No. 22, 1997, pp. 14033-14036.

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