Method for the production of (r)- and...

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing sulfur-containing organic compound

Reexamination Certificate

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Reexamination Certificate

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10493630

ABSTRACT:
The invention relates to a method for the production of (R)- or (S)-8-chloro-6-hydroxyoctanoic acid alkyl esters of the general formula (R)-II or (S)-IIin which R has the meaning C1-4-alkyl, from 8-chloro-6-oxooctanoic acid alkyl esters of the general formula Iin which R has the above meaning, by enzymatic reduction using alcohol dehydrogenases, such asLactobacillus brevisorThermoanaerobium brokii, in the presence of cofactor regeneration systems.The resulting (R)- and (S)-8-chloro-6-hydroxyoctanoic acid esters can be converted in a known manner into (R)-α-lipoic acid and (S)-α-lipoic acid, respectively.

REFERENCES:
patent: 19533882 (1997-03-01), None
patent: 0939132 (1999-09-01), None
patent: 939132 (1999-09-01), None
patent: 0210422 (2002-02-01), None
Fronza et al., J. Org. Chem, vol. 56, 1991, pp. 6019-6023.
Tsuboi et al., J. Org. Chen., vol. 63, 1998, pp. 1102-1108.
Ema et al., J. Org. Chem., vol. 66, pp. 8682-8694, 2001.
Fronza et al, “On the Mode of Bakers' Yeast Transformation of 3-Chloropropiophenone and Related Ketones,” J. Org. Chem, vol. 56, 1991, pp. 6019-6023.
Tsuboi et al, “Highly Enantioselective Synthesis of Both Enantiomers of gamma-substituted butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis,” J. Org. Chem, vol. 63, 1998, pp. 1102-1108.
Ema et al, “High Enantioselectivity and Broad Substrate Specificity of a Carbonyl Reductase,” J. Org. Chem, vol. 66, 2001, pp. 8682-8684.
Kleemann und Engel, “Pharmaceutical Substances,” 1999, pp. 1860-1861.

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