Chemistry: molecular biology and microbiology – Micro-organism – per se ; compositions thereof; proces of... – Bacteria or actinomycetales; media therefor
Reexamination Certificate
2001-09-26
2003-11-11
Saucier, Sandra E. (Department: 1651)
Chemistry: molecular biology and microbiology
Micro-organism, per se ; compositions thereof; proces of...
Bacteria or actinomycetales; media therefor
C435S252300
Reexamination Certificate
active
06645752
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a method of producing a corresponding &agr;-halo-&agr;,&bgr;-saturated carbonyl compound from an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond by hydrogenating the &agr;,&bgr;-carbon-carbon double bond using a microorganism belonging to the genus Acetobacter, Actinomyces, Acinetobacter, Agrobacterium, Aeromonas, Alcaligenes, Arthrobacter, Azotobacter, Bacillus, Brevibacterium, Burkholderia, Cellulomonas, Corynebacterium, Enterobacter, Enterococcus, Escherichia, Flavobacterium, Gluconobacter, Halobacteium, Halococccus, Klebsiella, Lactobacillus, Microbacterium, Micrococcus, Micropolyspora, Mycobacterium, Nocardia, Pseudomonas, Pseudonocardia, Rhodococcus, Rhodobacter, Serratia, Staphylococcus, Streptococcus, Streptomyces or Xanthomonas, preferably a microorganism belonging to the genus Pseudomonas or Burkholderia, more preferably Pseudomonas sp. SD810, Pseudomonas sp. SD811, Pseudomonas sp. SD812 or Burkholderia sp. SD816, or a microbial product thereof. The present invention also relates to novel microorganisms belonging to the genera Pseudomonas and Burkholderia, particularly Pseudomonas sp. SD810, Pseudomonas sp. SD811, Pseudomonas sp. SD812 and Burkholderia sp. SD816.
Furthermore, the present invention relates to a method of producing a corresponding &agr;-halo-&agr;,&bgr;-saturated carbonyl compound as an S form compound with respect to the &agr;-position from an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond by hydrogenating the carbon—carbon double bond. This method can be used in the production of optically active carbonyl compounds such as various optically active (having an absolute S form configuration at the &agr;-position) saturated carboxylic acids or amides. The optically active carbonyl compounds are a highly valuable chiral building block which is difficult to prepare by classical chemical processes, and are materials useful particularly as a raw material of medical or agricultural chemicals.
BACKGROUND OF THE INVENTION
In recent years, a method of producing various compounds, particularly optically active substances, by the reduction of a carbon—carbon double bond using a microorganism is drawing attention. To this effect, various methods of producing a corresponding &agr;,&bgr;-saturated carbonyl compound having a substituent at the &agr;-position from a carbonyl compound having an &agr;,&bgr;-carbon-carbon double bond and having a substituent at the &agr;-position by microbially reducing the carbon—carbon double bond have been reported (see, H. Simon, et al.,
Hoppe
-
Seyler's Z. Physiol. Chem.,
362, 33 (1981), H. Giesel, et al.,
Arch. Microbiol.,
135, 51 (1983), H. G. W. Leuenberger, et al.,
Helv. Chim. Acta.,
62, 455 (1979), R. Matsuno, et al.,
J. Ferm. Bioeng.,
84, 195 (1997)). However, for example, according to the method of using bacteria as the microorganism, an anaerobe such as
Clostridium kluyveri
(DSM-555) or Clostridium sp. La-1 (DSM-1460) is used. Therefore, the growing rate of the microorganism is slow, it is difficult to increase the cell concentration and accordingly, the reaction rate is not satisfactorily high. Thus, these methods have a problem in profitability and operability.
The method using
Clostridium theremosaccharolyticum
disclosed in JP-A-63-003794 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”) has an object of solving the above-descried problem by using a thermophilic bacterium. However, the bacterium used is still anaerobic, therefore, the growing rate and the reaction rate both are not satisfactorily high and the process involves use of hydrogen. Thus, the method fails in solving the problems in profitability and safety. Furthermore, the &agr;,&bgr;-saturated carbonyl compound having a substituent at the &agr;-position produced by reducing a prochiral carbonyl compound having an &agr;,&bgr;-carbon-carbon double bond and having a substituent at the &agr;-position using a microorganism is a compound having an absolute R form configuration and an S form configuration compound cannot be produced.
The method of reducing the &agr;,&bgr;-carbon-carbon double bond using a bread yeast as the microorganism has general-purpose applicability because compounds over a wide range can be reduced. In addition, since the microorganism used is aerobic, good operability can be attained. Furthermore, the optically active substances produced include both S form and R form, therefore, this method is most abundant in the cases reported. However, the yeast grows slowly as compared with bacteria, the optical selectivity is not sufficiently high in many cases in the reduction reaction for obtaining a more optically active product, and reduction of an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond is not known.
As described above, in the technique of producing a corresponding &agr;-halo-&agr;,&bgr;-saturated carbonyl compound from an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond by reducing the carbon—carbon double bond using a microorganism, a method satisfying all of the requirements regarding operability, profitability, safety and reaction properties is not yet known.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a method of producing a corresponding &agr;-halo-&agr;,&bgr;-saturated carbonyl compound from an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond by reducing the carbon—carbon double bond using a microorganism, which method can satisfy all of the requirements for operability, profitability, safety and reaction properties and ensure excellent optical selectivity.
As a result of thorough screening from soil, the present inventors have found that surprisingly, microorganisms capable of producing a corresponding &agr;-halo-&agr;,&bgr;-saturated carbonyl compound from an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond by reducing the carbon—carbon double bond are distributed over a relatively wide genus range of the aerobes and facultative anaerobes. In particular, it has been found that strains having this activity are present in a large number in microorganisms belonging to the genera Pseudomonas and Burkholderia, and some of these strains can reduce an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond and thereby produce an extremely high-purity &agr;-halo-&agr;,&bgr;-saturated carbonyl compound having an absolute configuration of S form at the &agr;-position. The present invention has been accomplished based on these findings.
More specifically, the present invention relates to the following embodiments:
[1] a method of producing an &agr;-halo-&agr;,&bgr;-saturated carbonyl compound from an &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond by reducing the &agr;,&bgr;-carbon-carbon double bond using a microorganism belonging to any one of the genera Acetobacter, Actinomyces, Acinetobacter, Agrobacterium, Aeromonas, Alcaligenes, Arthrobacter, Azotobacter, Bacillus, Brevibacterium, Burkholderia, Cellulomonas, Corynebacterium, Enterobacter, Enterococcus, Escherichia, Flavobacterium, Gluconobacter, Halobacteium, Halococccus, Klebsiella, Lactobacillus, Microbacterium, Micrococcus, Micropolyspora, Mycobacterium, Nocardia, Pseudomonas, Pseudonocardia, Rhodococcus, Rhodobacter, Serratia, Staphylococcus, Streptococcus, Streptomyces and Xanthomonas, or a microbial product thereof;
[2] the method of producing an &agr;-halo-&agr;,&bgr;-saturated carbonyl compound as described in [1], wherein the &agr;,&bgr;-carbon-carbon double bond of the &agr;-halocarbonyl compound having an &agr;,&bgr;-carbon-carbon double bond is reduced using a microorganism belonging to the genus Pseudomonas or a microbial product thereof;
[3] the method of producing an &agr;-halo-&agr;,&bgr;-saturated carbonyl compound as described in [1], wherein the &agr;,&bgr;-carbon-ca
Esaki Nobuyoshi
Kamachi Harumi
Kamachi Motoaki
Yoneda Tadashi
Saucier Sandra E.
Showa Denko Kabushiki Kaisha
Sughrue & Mion, PLLC
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