Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing alpha or beta amino acid or substituted amino acid...
Reexamination Certificate
2001-10-24
2003-01-07
Raymond, Richard L. (Department: 1624)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing alpha or beta amino acid or substituted amino acid...
C435S042000, C435S128000, C562S565000
Reexamination Certificate
active
06503739
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid by making use of the action of a lyase possessed by a microorganism.
S,S-2-Hydroxypropylenediamine-N,N′-disuccinic acid is a compound which is expected to be used in the fields of photography, detergents, paper making, etc. as a biodegradable chelating agent.
BACKGROUND ART
As to a process for producing 2-hydroxypropylenediamine-N,N′-disuccinic acid (hereinafter abbreviated as HPDDS), there have been disclosed a process for producing its stereoisomer mixture (a mixture of meso-compound and racemic modification) from maleic acid and 2-hydroxypropylenediamine (alias: 1,3-diamino-2-propanol) (cf. U.S. Pat. No. 3,158,635) and a process for producing its optically active S,S-isomer from S-aspartic acid, which is an optically active substance, and 1,3-dichloro-2-propanol (cf. Zhurnal Obshuchei Khimii, Vol. 49, p. 663, 1979). Further, it is known that among the three isomers of S,S-, R,R- and meso-, only the S,S-isomer is easily biodegradable (cf. JP-A-8-507805).
DISCLOSURE OF THE INVENTION
On the other hand, the present inventors have previously found a novel lyase activity of a microorganism which catalytically converts fumaric acid and ethylenediamine into S,S-ethylenediamine-N,N′-disuccinic acid (said lyase being hereinafter designated as ethylenediamine disuccinic acid ethylenediamine lyase and abbreviated as EDDS-ase) and proposed an economical and efficient process for producing an optically active aminopolycarboxylic acid which makes use of the above-mentioned catalytic action (cf. JP-A-9-140390). The inventors have further developed various technologies regarding the process for producing such optically active aminopolycarboxylic acids (cf., for example, JP-A-9-289895, JP-A-10-52292, JP-A-10-218846 and JP-A-10-271999). However, in almost all cases, an enzyme has a strict substrate specificity, and it has been utterly unknown whether HPDDS can be synthesized by the action of EDDS-ase or not.
The object of the present invention is to provide an economically advantageous process for producing S,S-HPDDS which does not use an expensive optically active substance.
The present inventors have made extensive study to attain the above-mentioned object and resultantly found that, by the action of EDDS-ase, S-2-hydroxypropylenediamine-N-monosuccinic acid is synthesized from one molecule of fumaric acid and one molecule of 2-hydroxypropylenediamine and further one molecule of fumaric acid reacts thereto, whereby S,S-HPDDS can be synthesized stereospecifically, and that S,S-HPDDS can be similarly synthesized from maleic acid and 2-hydroxypropylenediamine by combining the above-mentioned action of EDDS-ase with the action of maleic acid isomerase. The present invention has been accomplished on the basis of the above findings.
Thus, according to the present invention, there are provided
(1) a process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid which comprises producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid, in an aqueous medium containing fumaric acid and 2-hydroxypropylenediamine as substrates, from said substrates by the action of ethylenediamine disuccinic acid ethylenediamine lyase of a microorganism origin,
(2) a process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid which comprises producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid, in an aqueous medium containing maleic acid or maleic anhydride and 2-hydroxypropylenediamine as substrates, from said substrates by combined actions of ethylenediamine disuccinic acid ethylenediamine lyase and maleic acid isomerase each of a microorganism origin,
(3) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in (1) or (2) above wherein at least one metal ion selected from the group consisting of alkaline earth metals, iron, zinc, copper, nickel, aluminum, titanium and manganese is made to exist in the aqueous medium containing the substrates,
(4) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in (3) above wherein the metal ion is at least one metal ion selected from the group consisting of magnesium, manganese and iron,
(5) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in (1) or (2) above wherein a content of R-2-hydroxypropylenediamine-N-monosuccinic acid contained as an impurity in the aqueous medium containing the substrates is 2.5% by mole or less of the theoretical value of S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid to be formed,
(6) a process for producing an S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid alkali metal salt which comprises adding an alkali hydroxide to the reaction product mixture obtained in (3) or (4) described above to separate and recover as an insoluble precipitate the metal ions, which had been made to exist, and simultaneously to convert the S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid into its alkali metal salt,
(7) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in (3) or (4) above wherein the separated and recovered insoluble precipitate is reused as a metal ion source,
(8) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in any of (1) to (5) above which comprises adding at least one organic acid selected from the group consisting of fumaric acid, maleic acid and maleic anhydride to the reaction product mixture, recovering S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid or its salt as an insoluble substance and reusing the resulting supernatant for the reaction,
(9) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in any of (1) to (5) above which further includes the step of precipitating and recovering S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid as crystalline powder from the reaction product mixture under an acidic condition by use of a mineral acid,
(10) a crystalline powder of S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid in which the sum of contents of cyclic compounds represented by the following structural formulas [1] and [2] is 1% by mole or less relative to S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid,
(11) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in (1) above wherein the ethylenediamine disuccinic acid ethylenediamine lyase originates from a microorganism belonging to the genus Brevundimonas, the genus Paracoccus, the genus Sphingomonas, the genus Acidovorax, the genus Pseudomonas or the genus Burkholderia or from a microorganism transformed by a gene DNA which codes ethylenediaminedisuccinic acid ethylenediamine lyase of these microorganisms origin, and
(12) the process for producing S,S-2-hydroxypropylenediamine-N,N′-disuccinic acid described in (2) above wherein the ethylenediamine disuccinic acid ethylenediamine lyase originates from a microorganism belonging to the genus Brevundimonas, the genus Paracoccus, the genus Sphingomonas, the genus Acidovorax, the genus Pseudomonas or the genus Burkholderia or from a microorganism transformed by a gene DNA which codes ethylenediamine disuccinic acid ethylenediamine lyase of these microorganisms origin and the maleic acid isomerase originates from a microorganism belonging to the genus Alcaligenes, the genus Pseudomonas, the genus Xanthomonas or the genus Bacillusor or from a microorganism transformed by a gene DNA which codes maleic acid isomerase of these microorganisms origin.
BEST MODE FOR CARRYING OUT THE INVENTION
Cultivation of Microorganism
The microorganisms used in the present invention are as described later.
The kind of culture media for the microorganism used in the present invention is not particularly limited and both a synthetic medium and a natural medium may be used so long as they appropri
Mitsubishi Rayon Co. Ltd.
Tucker Zachary C.
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