Process for producing levodione

Details Process for producing levodione Process for producing levodione

2000-07-28

2002-08-06

Lankford, Jr., Leon B. (Department: 1651)

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing oxygen-containing organic compound

C435S071100, C435S132000, C424S195160

Reexamination Certificate

active

06428991

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to the microbial production of (6R)-2,2,6-trimethylcyclohexane-1,4-dione (hereinafter referred to as levodione), a useful intermediate in the production of carotenoids, such as (3R,3′R)-zeaxanthin. More particularly, the present invention relates to a process for producing levodione of high purity and in high yield by the catalytic reaction of 2,6,6-trimethyl-2-cyclohlexene-1,4-dione (hereinafter referred to as ketoisophorone) with a specific yeast.
BACKGROUND OF THE INVENTION
Levodione has previously been prepared through the reduction of the carbon-carbon double bond in ketoisophorone by contacting the ketoisophorone with baker's yeast, such as
Saccharomyces cervisiae,
which functions as an enantioselective biocatalyst (Biotechnology of Vitamins, Pigments and Growth Factors, Ed. Erick J. Vandamme, page 71, Elsevier Applied Science, London and New York). However, baker's yeast is not suitable for use in the industrial production of levodione because the yields are too low. In addition, the use of baker's yeast in the production of levodione is inefficient because the yeast cells cannot be reused because of the short lifetime of the reaction activity of the yeast. In addition, a complicated purification process is necessary when baker's yeast is used in the production process because it is difficult to separate the yeast from the culture solution after the catalytic reaction.
SUMMARY OF THE INVENTION
One embodiment of the invention is a process for producing (6R)-2,2,6-trimethylcyclohexane-1,4-dione. This process includes contacting, in a reactor, 2,6,6-trimethyl-2-cyclohexene-1,4-dione with a yeast selected from the group consisting: of
Saccharomyces rouxii
(
Zygosaccharomyces rouxii
),
Saccharomyces delbrueckii
(
Saccharomyces unisporus, Torulaspora delbrueckii
),
Saccharomyces willianus, Zygosaccharomyces bailii, Candida tropicalis,
functional equivalents, subcultures, mutants, and variants thereof, in water, a water-miscible organic solvent, or a mixture of water and the water-miscible organic solvent containing at least one assimilable carbon source; and isolating (6R)-2,2,6-trimethylcyclohexane-1,4-dione produced by the yeast from the reaction medium.
Another embodiment of the invention is a process for producing (6R)-2,2,6-trimethylcyclohexane-1,4-dione. This process includes contacting 2,6,6-trimethyl-2-cyclohexene-1,4-dione with a reaction medium containing yeast, an aqueous solvent, and at least one assimilable carbon source, wherein the yeast is selected from the group of
Saccharomyces rouxii
(
Zygosaccharomyces rouxii
),
Saccharomyces delbrueckii
(
Saccharomyces untisporus, Torulaspora delbrueckii
),
Saccharomyces willianus, Zygosaccharomyces bailii, and Candida tropicalis.
The (6R)-2,2,6-trimethylcyclohexane-1,4-dione produced by the yeast is then isolated from the reaction medium.
A further embodiment of the invention is process for producing (6R)-2,2,6-trimethylcyclohexane-1,4-dione. This process includes entrapping yeast cells within a carrier made of a hydrophobic photo-crosslinkable resin having at least two ethylenic unsaturated linkages per molecule, wherein the yeast cells are selected from the group of
Saccharomyces rouxii
(
Zygosaccharomyces rouxii
),
Saccharomyces delbrueckii
(
Saccharomyces unisporus, Torulaspora delbrueckii
),
Saccharomyces willianus, Zygosaccharomyces bailii, and Candida tropicalis.
The resin is then irradiated with UV light to form a polymerized yeast carrier. The yeast in the yeast carrier is then preconditioned in a growth medium containing at least one assimilable carbon source, an assimilable nitrogen source, and inorganic salts. 2,6,6-trimethyl-2-cyclohexene-1,4-dione is then added to a reaction medium containing the preconditioned yeast cells from the previous step, an aqueous solvent, and at least one assimilable carbon source. Then, the (6R)-2,2,6-trimethylcyclohexane-1,4-dione produced by the yeast is isolated from the reaction medium.


REFERENCES:
patent: 3960966 (1976-06-01), Widmer et al.
patent: 4072715 (1978-02-01), Boguth et al.
patent: 4156100 (1979-05-01), Boguth et al.
patent: 0864600 (1998-09-01), None
Nelis, et al., “Microbial Production of Carotenoids,” inBiotechnology of Vitamins, Pigments and Growth Factors, Ed. Erick J. Vandamme, Elsevier Applied Science, London and New York, pp. 71-73 (1989).
Powell, “Immobilized Biocatalyst Technology,”Microbial Enzymes and Biotechnology, 2nd Edition, Ed. William M. Fogarty and Catherine T. Kelly, Elsevier Applied Science, London and New York, pp. 369-394 (1990).
Derwent English language abstract of JP 61265/1994.

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