Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Reexamination Certificate
2000-07-25
2002-04-02
Saucier, Sandra E. (Department: 1651)
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Resolution of optical isomers or purification of organic...
Reexamination Certificate
active
06365399
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for producing a carboxylic acid isomer.
2. Description of the Related Art
Carboxylic acids are widely used as intermediates of medicines such as an anti-inflammatory agent and the like and intermediates of agricultural chemicals such as a herbicide and the like, and optical isomers corresponding to the configurations of intended medicines and agricultural chemicals are required.
A method for producing a compound using a microorganism, so called bioconversion method can be generally conducted under mild condition, and is effective in small waste load, and the like and recognized as an advantageous method. There is known a method in which a certain microorganism is allowed to act on a compound (X) represented by the general formula (X):
(wherein, L′ is an aryl group or aryloxy group.) to produce a compound (Y) represented by the general formula (Y):
(wherein, L′ has the same meaning as defined above.), according to a bioconversion method (Japanese Patent Application Laid-Open (JP-A) No. 2-65785, J. Appl. Microbiol., 85, 155-163 (1998), JP-A Nos. 60-43388, 60-43389, and the like.). However, the compound obtained by this method is limited to the compound (Y), and a method for producing the reverse optical isomer efficiently has been required.
SUMMARY OF THE INVENTION
Under such conditions, the present inventors have intensively studied, a process for producing a carboxylic acid isomer, and resultantly found a microorganism having an ability to produce a carboxylic acid isomer B represented by the general formula (2):
(wherein, L is a C
6
to C
14
aryl group which may optionally been substituted, C
4
to C
12
heteroaryl group which may optionally been substituted, C
6
to C
14
aryloxy group which may optionally been substituted or C
4
to C
12
heteroaryloxy group which may optionally been substituted, and M is an C
1
to C
3
alkyl group.), (hereinafter, referred to as the carboxylic acid isomer B(2)) by reversing the configuration based on an asymmetric carbon atom of a carboxylic acid, and further found that the carboxylic acid isomer B(2) can be obtained in high yield by using this microorganism, leading to completion of the present invention.
Namely, the present invention provide:
1. A process for producing a carboxylic acid isomer B represented by the general formula (2):
(wherein, L is a C
6
to C
14
aryl group which may optionally been substituted, C
4
to C
12
heteroaryl group which may optionally been substituted, C
6
to C
14
aryloxy group which may optionally been substituted or C
4
to C
12
heteroaryloxy group which may optionally been substituted, and M is an C
1
to C
3
alkyl group.), which comprises:
allowing a carboxylic acid isomer A represented by the general formula (1):
(wherein, L and M have meanings as defined above.) to contact with a microbiological material having an ability to convert the carboxylic acid isomer A(1) into the carboxylic acid isomer B(2).
2. The process according to the above 1, wherein L in the carboxylic acid isomer A(1) is a C
6
to C
14
aryl group which may optionally been substituted or C
4
to C
12
heteroaryl group which may optionally been substituted.
3. The process according to the above 1, wherein M in the carboxylic acid isomer A(1) is a methyl group.
4. The process according to the above 1, wherein the microbiological material is a cultured broth of microbial cells, microbial cells or materials obtainable by treating a microorganism belonging to Actinomycetes group.
5. The process according to the above 1 wherein the microbiological material is a cultured broth of microbial cells, microbial cells or materials obtainable by treating a microorganism belonging to the genus Nocardia.
6. The process according to the above 1, wherein the microbiological material is a cultured broth of microbial cells, microbial cells or materials obtainable by treating a microorganism of Nocardia diaphanozonaria JCM3208 or a mutant thereof.
7. The process according to the above 1 wherein the microbiological material is a cultured broth of microbial cells, microbial cells or materials obtainable by treating a microorganism belonging to the genus Saccharopolyspora.
8. The process according to the above 1, wherein the microbiological material is a cultured broth of microbial cells, microbial cells or materials obtainable by treating a microorganism of Saccharopolyspora hirsuta subsp. Kobensis JCM 9109 or a mutant thereof.
9. A process for improving the optical purity of a carboxylic acid isomer B represented by the general formula (2):
(wherein, L is a C
6
to C
14
aryl group which may optionally been substituted, C
4
to C
12
heteroaryl group which may optionally been substituted, C
6
to C
14
aryloxy group which may optionally been substituted or C
4
to C
12
heteroaryloxy group which may optionally been substituted, and M is an C
1
to C
3
alkyl group.), which comprises:
allowing a carboxylic acid by the general formula (3):
L—CH(M)—COOH
(wherein, L and M have meanings as defined above.) to contact with a microbiological material having an ability to convert a carboxylic acid isomer A represented by the general formula (1):
(wherein, L and M have meanings as defined above.) into the carboxylic acid isomer B(2).
10. A use of a microbiological material having an ability to convert a carboxylic acid isomer A represented by the general formula (1):
(wherein, L is a C
6
to C
14
aryl group which may optionally been substituted, C
4
to C
12
heteroaryl group which may optionally been substituted, C
6
to C
14
aryloxy group which may optionally been substituted or C
4
to C
12
heteroaryloxy group which may optionally been substituted, and M is an C
1
to C
3
alkyl group.)
into a carboxylic acid isomer B represented by the general formula (2):
(wherein, L and M have meanings as defined above.). for converting the carboxylic acid isomer A(1) into the carboxylic acid isomer B(2).
Further scope of applicability of the present invention will become apparent from the detailed description given hereinafter. However, it should be understood that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
Throughout this specification and the claims which follow, unless the context requires otherwise, the word “comprise”, and variations such as “comprises” and “comprising”, will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integer or step.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
In the process of the present invention, L in the carboxylic acid isomer A(1) is a C
6
to C
14
aryl group which may optionally been substituted (i.e. C
6
to C
14
aryl group or substituted C
6
to C
14
aryl group), C
4
to C
12
heteroaryl group which may optionally been substituted (i.e. C
4
to C
12
heteroaryl group or substituted C
4
to C
12
heteroaryl group), C
6
to C
14
aryloxy group which may optionally been substituted (i.e. C
6
to C
14
aryloxy group or substituted C
6
to C
14
aryloxy group) or C
4
to C
12
heteroaryloxy group which may optionally been substituted (i.e. C
4
to C
12
heteroaryloxy group or substituted C
4
to C
12
heteroaryloxy group). Examples of the C
6
to C
14
aryl group include a phenyl group, naphthyl group and the like. Preferable examples of the C
4
to C
12
heteroaryl group include those containing, as a hetero atom, 1 to 4 of at least one kind of atom among nitrogen, oxygen and sulfur atoms, and there specifically are listed
and the like.
Examples of the C
6
to C
14
aryloxy group include a phenyloxy group, naphthyloxy group and the like. Preferable examples of the C
4
to C
12
heteroaryloxy group include those containing, as a hetero at
Kobayashi Yuko
Takashima Yoshiki
Saucier Sandra E.
Sughrue & Mion, PLLC
Sumitomo Chemical Company Limited
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