Methods for producing optically active amino acids

Details Methods for producing optically active amino acids Methods for producing optically active amino acids

2000-03-29

2004-08-24

Marx, Irene (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...

C435S106000, C435S128000, C435S136000

Reexamination Certificate

active

06780633

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method for producing an optically active amino acid and the like.
2. Description of the Prior Art
An optically active amino acid is known to be a compound which is useful as an intermediate for a pharmaceutical such as an anti-asthmatic agent, an anti-depressant and an anti-thrombotic agent and as a feed or food additive and the like.
A biochemical method for producing an optically active amino acid is believed generally to be advantageous in terms of the simplicity of an operation, the yield of a product, the prices of starting materials and the optical purity of an intended substance when compared with a synthetic chemical method. Such biochemical method may for example be a method in which one of the optical isomers of an amino acid as a racemic mixture is decomposed, a method in which an aminoacyl-form of an amino acid as a racemic mixture is deacylated in an optically selective manner, a method in which an amino acid as a L-form is produced from a keto acid in the presence of an amino-donating compound and a method utilizing a fermentation of a microorganism.
SUMMARY OF THE INVENTION
An objective of the present invention is to provide a method for producing an optically active amino acid effeciently.
Now we discovered a biological material which has an ability of converting one of the optical isomers of a certain amino acid to the other of the optical isomers, the isomerism being on the basis of an asymmetric carbon atom to which both of an amino group and a carboxyl group are bound and the ability described above being not inhibited seriously by an aminotransferase inhibitor-chloro-D-alanine, -chloro-L-alanine or gabaculine, and finally established the present invention by applying said biological material to the production of an optically active amino acid of the amino acid described above.
That is, the present invention provides:
1. A method for producing from one of the optical isomers (optical isomer I) of an amino acid represented by Formula (1):
R—CH(NH2)—COOH  (1)
 (wherein R is an optionally substituted C1-C12 alkyl group, an optionally substituted C4-C8 cycloalkyl group or an optionally substituted C6-C14 aryl group) (hereinafter, it is sometimes referred to as the amino acid (1)) the other of the optical isomers (optical isomer II), said method comprising reacting a biological material which has an ability of converting said one of the optical isomers (optical isomer I) to said the other of the optical isomers (optical isomer II), the isomerism being on the basis of an asymmetric carbon atom to which both of an amino group and a carboxyl group are bound and said ability being not inhibited seriously by an aminotransferase inhibitor -chloro-D-alanine, -chloro-L-alanine or gabaculine, with said one of the optical isomers (optical isomer I). (Hereinafter, it is sometimes referred to as the method of the present invention.)
2. the method according to the above 1, wherein said one of the optical isomers (optical isomer I) is a D-form and said the other of the optical isomers (optical isomer II) is a L-form.
3. the method according to the above 1, wherein said one of the optical isomers (optical isomer I) with which said biological material is reacted is present in a mixture of said the other of the optical isomers (optical isomer II).
4. the method according to the above 1, wherein said biological material is a whole cell.
5. the method according to the above 1, wherein said biological material is one derived from a microorganism belonging to the genus Arthrobacter, Flavimonas, Klebsiella, Nocardia, Pseudomonas, Rhizobium, Saccharopolyspora or Streptomyces.
6. the method according to the above 1, wherein said biological material is one derived from a microorganism classified to
Arthrobacter pascens, Flavimonas oryzihabitans, Klebsiella planticola, Nocardia diaphanozonaria, Pseudomonas chlororaphis, Pseudomonas oleovorans, Pseudomonas oxalaticus, Pseudomonas taetrolens, Rhizobium meliloti, Saccharopolyspora hirsuta or Streptomyces roseus.
7. the method according to the above 1, wherein said biological material is one derived from
Arthrobacter pascens
strain IFO12139
, Flavimonas oryzihabitans
strain JCM2952
, Klebsiella planticola
strain JCM7251
, Nocardia diaphanozonaria
strain JCM3208,
Pseudomonas chlororaphis
strain IFO3521
, Pseudomonas oleovorans
strain IFO13583
, Pseudomonas oxalaticus
strain IFO13593
, Pseudomonas taetrolens
strain IFO3460
, Rhizobium meliloti
strain IFO14782
, Saccharopolyspora hirsuta
subsp.kobensis strain JCM9109 or
Streptomyces roseus
strain IFO12818.
8. a method for improving the optical purity of an amino acid represented by Formula (1):
R—CH(NH2)—COOH  (1)
(wherein R is an optionally substituted C1-C12 alkyl group, an optionally substituted C4-C8 cycloalkyl group or an optionally substituted C6-C14 aryl group), said method comprising reacting a biological material which has an ability of converting one of the optical isomers (optical isomer I) of said amino acid to the other of the optical isomers (optical isomer II), the isomerism being on the basis of an asymmetric carbon atom to which both of an amino group and a carboxyl group are bound and said ability being not inhibited seriously by an aminotransferase inhibitor &bgr;-chloro-D-alanine, &bgr;-chloro-L-alanine or gabaculine, with said amino acid represented by Formula (1).
9. the method according to the above 8, wherein said one of the optical isomers (optical isomer I) is a D-form and said the other of the optical isomers (optical isomer II) is a L-form.
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 INVENTION
The invention is described in detail below.
A biological material which can be employed in the present invention is a biological material which has an ability of converting one of the optical isomers (optical isomer I) of the amino acid (1) to the other of the optical isomers (optical isomer II), the isomerism being on the basis of an asymmetric carbon atom to which both of an amino group and a carboxyl group are bound and the ability being not inhibited seriously by an aminotransferase inhibitor &bgr;-chloro-D-alanine, &bgr;-chloro-L-alanine or gabaculine (hereinafter sometimes referred to as the biological material of the present invention).
The ability being not inhibited seriously by an aminotransferase inhibitor &bgr;-chloro-D-alanine, &bgr;-chloro-L-alanine or gabaculine described herein means that the converting ability in the presence of an inhibitor is about 70% or more of thrat in the absence of the inhibitor when assuming the ability in the absence of the inhibitor to be 100%. Furthermore, it is preferred to be the ability being not inhibited substantially by an aminotransferase inhibitor &bgr;-chloro-D-alanine, &bgr;-chloro-L-alanine or gabaculine described herein means that the converting ability in the presence of an inhibitor is about 90% or more of that in the absence of the inhibitor when assuming the ability in the absence of the inhibitor to be 100%.
While a conversion reaction described above involves the formation of a product (optical isomer II) corresponding to the consumption of a substrate (optical isomer I) until an equilibrium

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