JPH08134021A - Carbonate compound and its production - Google Patents

Abstract

PURPOSE: To obtain a new carbonate compound extremely useful as a synthetic raw material for medicines, agrochemicals, other physiologically active substances and further a new material such as a liquid crystal material. CONSTITUTION: A carbonate compound of formula I (R<1> is an alkyl), e.g. 3- chloro-2-methoxycarbonyloxy-1-propanol. This compound is obtained by reacting a dicarbonate compound of formula II (R<2> is an alkyl) as a substrate with a culture solution, a microbial cell or a treated substance of a microorganism, belonging to the genus Bacillus, Brevibacterium, Corynebacterium, Micrococcus, Xanthomonas, Nocardia or Rhodococcus and having the ability to selectively hydrolyze an alkoxycarbonyl group in the terminal part of the carbon chain of the dicarbonate compound when reacting the dicarbonate compound therewith. The compound of formula II is obtained by reacting, e.g. 3-chloro-1,2-propanediol with a monoalkyl halogenocarbonate in the presence of a base.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a carbonate compound and a method for producing the same.

[0002]

2. Description of the Related Art 3-Chloro-1,2-propanediol is easy to introduce other functional groups in place of chlorine and hydroxyl groups bound to the compound, and is used as a drug, a pesticide, other physiologically active substance, and a liquid crystal material. It is an extremely important compound as a raw material for the synthesis of new materials such as.

However, in order to convert 3-chloro-1,2-propanediol into a desired derivative, one of two hydroxyl groups having similar reactivity is often protected with some protecting group. There is a need.

Conventionally, as a method for protecting the hydroxyl group of 3-chloro-1,2-propanediol, 3-chloro-
A method in which 1,2-pronediol and a protecting agent are not directly reacted but epichlorohydrin is reacted with benzyl alcohol or a carboxylic acid to protect the primary alcohol at the end of the carbon chain with a benzyl group or an acyl group is proposed. It was common. (JP-A-61-189258, JP-A-61-271240).

[0005]

However, in such a process, the compound obtained is a primary alcohol protected 3-chloro-1,2-propanediol derivative. That is, 2 of 3-chloro-1,2-propanediol
Derivatives in which only grade alcohols are protected have not been known, although they have high value as industrial raw materials for various applications.

[0006]

The present inventors have found useful 3
We have continued diligent studies to develop a -chloro-1,2-propanediol derivative. As a result, 3-chloro-1,
The two hydroxyl groups of 2-propanediol are protected by an alkoxycarbonyl group, and a carbonate compound represented by a specific general formula is used as a substrate, and a specific microbial culture solution, microbial cells or a treated product of microbial cells is allowed to act on the carbonate compound. As a result, it was found that a useful carbonate compound in which only the primary alcohol at the end of the carbon chain was hydrolyzed was obtained, and the present invention was completed.

That is, the present invention has the following general formula (I)

[0008]

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(R ¹ is an alkyl group) is a carbonate compound.

In the general formula (I), R ¹ represents an alkyl group. The alkyl group may be linear or branched, and the carbon number thereof is not particularly limited. From the viewpoint of ease of production, an alkyl group having 1 to 4 carbon atoms is preferable. Specific examples of suitable alkyl groups in the present invention include methyl group, ethyl group, n-propyl group, i
so-propyl group, n-butyl group, iso-butyl group,
Examples thereof include t-butyl group.

Specific examples of the carbonate compound represented by the general formula (I) include 3-chloro-2-methoxycarbonyloxy-1-propanol and 3-chloro-
2-ethoxycarbonyloxy-1-propanol, 3
-Chloro-2-n-propoxycarbonyloxy-1-
Propanol, 3-chloro-2-iso-propoxycarbonyloxy-1-propanol, 3-chloro-2-
n-butoxycarbonyloxy-1-propanol, 3
-Chloro-2-iso-butoxycarbonyloxy-1
-Propanol, 3-chloro-2-t-butoxycarbonyloxy-1-propanol and the like can be mentioned.

The carbonate compound represented by the general formula (I) may be produced by any method. For example, only the primary alcohol was protected from 3-chloro-1,2-propanediol by the method described above.
Producing a chloro-1,2-propanediol derivative,
The secondary alcohol can be produced by protecting the primary alcohol with another protective group having different removal conditions and then removing the protective group from the primary alcohol. It is preferably produced by the method.

That is, in the present invention, the above general formula (I)
The carbonate compound represented by Bacillus, Brevibacterium, Corynebacterium, Flavobacterium, Micrococcus, Xanthomonas, Nocardia, Rhodococcus, and the following general formula (II)

[0014]

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When reacted with a dicarbonate compound represented by the formula (R ² is an alkyl group), the following general formula (I)

[0016]

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(R ¹ is an alkyl group.) A solution of a microorganism having the ability to form a carbonate compound represented by the formula, a bacterial cell or a treated product of the bacterial cell is allowed to act on the compound represented by the general formula (II). It is preferably obtained by a method of collecting the produced carbonate compound represented by the general formula (I).

Here, the above general formula (II)

[0019]

[Chemical 4]

In the dicarbonate compound represented by (R ² is an alkyl group), the alkyl group of R ² is
It is the same as the alkyl group of R ^{1 represented by} the general formula (I).

Specific examples of the dicarbonate compound represented by the general formula (II) include 3-chloro-1,2-
Dimethoxycarbonyloxypropane, 3-chloro-
1,2-diethoxycarbonyloxypropane, 3-chloro-1,2-di-n-propoxycarbonyloxypropane, 3-chloro-1,2-di-iso-propoxycarbonyloxypropane, 3-chloro- 1,2-
Examples thereof include di-n-butoxycarbonyloxypropane, 3-chloro-1,2-di-iso-butoxycarbonyloxypropane and 3-chloro-1,2-di-t-butoxycarbonyloxypropane.

In the present invention, such a dicarbonate compound represented by the general formula (II) is used as a substrate, on which Bacillus, Brevibacterium, Corynebacterium, Flavobacterium, Micrococcus, Xanthomonas, A culture solution, a microbial cell or a treated product of a microorganism belonging to the genus Nocardia or the genus Rhodococcus and having the ability to selectively hydrolyze the alkoxycarbonyl group at the end of the carbon chain when the dicarbonate compound is allowed to act. To act.

Thereby, the compound represented by the general formula (I) is produced in a good yield. Here, the above-mentioned microorganism can be used without any limitation as long as it has the above-mentioned properties. Specifically, Bacillus subtilis
subtillis IFO 3007), Bacillus subtillis var.aterrimus IFO
3038), Bacillus circulan
s IFO 3329), Bacillus s
phaericus IFO 3341), Brevibacterium divaricatum NRRL 231
1), Corynebacterium glutamicum No. 53
4 (Corynebacterium glutamicum No.534 ATCC 1303
2), Flavobacterium Esteraromaticum (F
lavobacterium esteroaromaticum IFO 3751), Micrococcus roseus IFO 376
8), Xanthomonas translucence
translucens IFO 13558), Nocardia asteroides IFO 3384, Nocardia autotrophica IFO 1274
3), Rhodococcus equi ATCC 7
698) and the like are preferably used.

As a medium used for culturing the above-mentioned microorganism, a known medium is used. For example, glucose, sucrose, fructose, glycerol,
Carbon sources such as sorbitol, honey, soluble starch, nitrogen sources such as meat extract, yeast extract, polypeptone, peptone, nitrates, ammonium salts, etc., and primary potassium phosphate, secondary potassium phosphate, sodium chloride, magnesi nitrate. There is no particular limitation as long as it contains an inorganic salt such as parrot.

The form of the medium may be liquid or solid. The culture method may be static culture, shaking culture, or aeration-agitation culture, but liquid culture by aeration-agitation is suitable for large-scale culture. The culture temperature is 15 to 45 ° C,
Preferably, the culture is performed at 20 to 40 ° C. for usually 20 to 48 hours.

In the present invention, the method of causing the culture solution, cells, or treated product of cells of the above-mentioned microorganism to act on the above-mentioned substrate may be any method for acting on the substrate which is usually used in the enzymatic reaction utilizing the microorganism. Adopted without restrictions. For example, a method in which the substrate is allowed to act by adding the substrate to the culture medium of the microorganism is mentioned. In this case, the substrate may be added to the medium from the beginning or may be added during the culture.

The substrate may be allowed to act on the substrate in the inorganic or organic solvent that does not inhibit the reaction, preferably in an aqueous solvent. Incidentally, in the present invention, the treated cells are, for example, washed cells,
There is no particular limitation on dried bacterial cells, ground bacterial cells, autolyzed bacterial cells, sonicated bacterial cells, bacterial cell extracts, or lipases obtained by purifying bacterial cell extracts. used. Here, as the cells, the cell extract, and the lipase obtained by purifying the cell extract, those immobilized by a known cell or enzyme immobilization method can be used.

In the present invention, the concentration of the substrate when the culture solution of the microorganism thus obtained, the cells or the treated product of the cells is allowed to act is not particularly limited. Usually 0.0
1 to 10% by weight, preferably 0.05 to 5% by weight
It can be adopted from

In the present invention, the pH of the reaction medium when the culture solution of the microorganism, the cells or the treated product of the cells is thus acted is not particularly limited, but is usually pH 6 It is preferably in the range of -9. further,
The concentration of the microbial cells or the treated product of the microbial cells at the time of action cannot be unconditionally determined due to the difference in the degree of purification of the treated microbial cells, but usually the amount of protein is 0.05 to 10% by weight.
It is appropriately adopted from the range. The working temperature is not particularly limited, but is 10 to 50 ° C., preferably 30 to 50 ° C.
A range of 45 ° C is preferred. The action time cannot be unconditionally determined because it depends on the substrate concentration and the type of strain to be used, but it is usually sufficient to act for 3 to 80 hours.

After carrying out the hydrolysis reaction of the substrate as described above, the produced carbonate compound represented by the general formula (I) is collected. The method for collecting this product is not particularly limited, and for example, the reaction solution is extracted with an organic solvent such as ethyl acetate or methylene chloride, the solvent is distilled off, and the residue is easily separated by thin layer chromatography. Separation and purification can be performed.

Next, in the present invention, the dicarbonate compound represented by the general formula (II) used in the method for producing the carbonate compound represented by the general formula (I) by the above-mentioned enzymatic method can be produced by any method. You may use the thing. The following method can be mentioned as a typical manufacturing method. That is, a method of reacting 3-chloro-1,2-propanediol with a halogenated carbonic acid monoalkyl ester in the presence of a base can be mentioned.

Here, as the halogen of the halogenated carbonic acid monoalkyl ester, chlorine, bromine, iodine and the like can be used without any limitation.

Further, examples of the base include tertiary amines and alkali metal carbonates. Specific examples thereof include triethylamine, tripropylamine, tributylamine, methyldiisopropylamine, N, N, N ', N'-tetramethylethylenediamine, N, N, N', N '. An aliphatic tertiary amine such as tetramethylpropylenediamine, an aromatic tertiary amine such as pyridine, 4-dimethylaminopyridine, N, N-dimethylbenzylamine, N, N-dimethylaniline and the like, and an alkali Examples of metal carbonates include sodium carbonate and potassium carbonate.
The charging molar ratio of the base to the compound represented by the general formula (II) may be appropriately determined as necessary, but it is generally 2 to 10 times mol, preferably 2 to 5 times mol. Target.

The charging molar ratio of 3-chloro-1,2-propanediol and chlorocarbonic acid monoalkyl ester may be appropriately determined according to need, but is usually 2 to 10.
It is generally used in a molar range of 2 times, preferably 2 to 5 times.

This reaction is generally preferably carried out in an organic solvent. Examples of suitable organic solvents include dioxane, tetrahydrofuran, diethyl ether,
Ethers such as diisopropyl ether; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; N, N-dimethylformamide, N, N- Amides such as dimethylacetamide; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate and isopropyl acetate; aromatic hydrocarbons such as toluene, benzene and xylene; halogenated aromatic hydrocarbons such as chlorobenzene Can be mentioned.

The reaction time varies depending on the desired type of the dicarbonate compound represented by the general formula (II) and cannot be particularly limited, but it is preferably selected from the range of 1 to 30 hours.

The reaction temperature varies depending on the compound and cannot be particularly limited, but is usually from -20 to 10.
It is preferable to select from the range of 0 ° C, preferably -10 to 80 ° C.

The above-mentioned general formula (I
The method for isolating and purifying the dicarbonate compound represented by I) is not particularly limited, and a known method may be appropriately adopted.
For example, when water is added to the reaction solution to dissolve the precipitated salt and then the reaction is performed in an organic solvent that dissolves in water,
Furthermore, extraction may be performed by adding an organic solvent that is insoluble in water.

When the reaction is carried out in an organic solvent which does not dissolve in water, water may be added to the above reaction solution and then extraction may be carried out with that solvent.

After washing with water, the organic solvent is dried with a desiccant such as anhydrous sodium sulfate or anhydrous magnesium sulfate, the organic solvent is distilled off, and the residue is separated and purified by column chromatography or vacuum distillation. The target product can be obtained.

In the present invention, the structures of the carbonate compound represented by the general formula (I) and the dicarbonate compound represented by the general formula (II) can be confirmed by the following means.

(1) ¹ H-nuclear magnetic resonance spectrum ( ¹ H-
By measuring (NMR), the bonding mode of hydrogen atoms present in the compounds represented by the general formulas (I) and (II) can be known.

(2) By measuring the infrared absorption spectrum (IR), the characteristic absorption derived from the functional groups of the compounds represented by the general formulas (I) and (II) can be observed. In the compound represented by the general formula (I), 170
Absorption due to C = O bond near 0 to 1780 cm ^-1 ,
Absorption due to the O—H bond can be observed in the vicinity of 3300 to 3600 cm ⁻¹ . In addition, the general formula (II)
In the compound represented by, absorption based on C═O bond can be observed in the vicinity of 1700 to 1780 cm ⁻¹ .

(3) Mass spectrum (MS) is measured,
The molecular ion peaks (hereinafter abbreviated as M ⁺ ) of the general formulas (I) and (II) are observed. Therefore, the molecular weight can be determined.

(4) By the elemental analysis, the weight% of oxygen can be calculated by subtracting the sum of the weight% of carbon, hydrogen, chlorine and each element from 100, and therefore the composition formula can be determined.

[0046]

INDUSTRIAL APPLICABILITY The carbonate compound represented by the general formula (I) of the present invention can easily introduce various substituents into the hydroxyl group at the terminal of the carbon chain. Then, the obtained compound can also easily remove the alkoxycarbonyl group in which the secondary alcohol is protected by alkaline hydrolysis, and various functional groups can be easily introduced in place of this. Therefore, the compound is
In 3-chloro-1,2-propanediol, it is extremely effective as an industrial raw material for various uses in which it is required to introduce a functional group into the primary alcohol part first and then subject the secondary alcohol part to the reaction. Can be used.

The carbonate compounds are Bacillus, Brevibacterium, Corynebacterium,
A culture solution, a microbial cell, or a treated product of a specific microorganism belonging to the genus Flavobacterium, the genus Micrococcus, the genus Xanthomonas, the genus Nocardia, and the genus Rhodococcus is allowed to act on the dicarbonate compound represented by the general formula (II). Therefore, it can be easily manufactured and is extremely useful.

[0048]

EXAMPLES The present invention will be described below with reference to examples.
The invention is in no way limited to these examples.

Example 1 ((Synthesis of Substrate)) 3-chloro-1,2-propanediol 3 was placed in a four-necked flask equipped with a stirrer and a thermometer.
3.2 g (0.3 mol), pyridine 79.1 g (1.
(0 mol) was dissolved in 300 ml of methylene chloride, and the mixture was stirred under ice cooling, and 72.4 g of methyl chlorocarbonate was added to this mixed solution.
(0.9 mol) was added dropwise over 1 hour so that the internal temperature was 10 ° C or lower. After stirring for 4 hours, 200 ml of methylene chloride was added to the reaction solution and washed with 200 ml of water. Furthermore, this methylene chloride solution was washed with 200 ml of 2% hydrochloric acid and 200 ml of water and then dried over magnesium sulfate, and the solvent was distilled off. The obtained yellow transparent liquid was added to 0.4T
When the vacuum distillation is performed at orr and 140 ° C., 3-chloro-
1,2-dimethoxycarbonyloxypropane was added to 58.
0 g (85%) was obtained.

As a result of measuring the infrared absorption spectrum of this product, an absorption based on a carbonyl group was obtained at 1753 cm ^-1 . The elemental analysis values are C37.00%, H4.88.
%, Cl 15.78%, and the composition formula is C ₇ H ₁₁ ClO.
C37.10, which is the calculated value for ₆ (226.61)
%, H 4.89%, Cl 15.65%.
Further, as a result of measuring a mass spectrum, a peak corresponding to M ⁺ was shown at m / e 226.

Further, the result of measurement of ¹ H-nuclear magnetic resonance spectrum (δ: ppm: tetramethylsilane standard; deuterated chloroform solvent) was as follows.

[0052]

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A multiplet of two protons was shown at 3.73 to 3.77 ppm and corresponded to the methylene proton of (c). A singlet for three protons is shown at 3.80 ppm,
Corresponding to the methyl proton in (e). A singlet for three protons was shown at 3.82 ppm, which corresponded to the methyl proton in (d). Multiple lines corresponding to two protons were shown at 4.31 to 4.48 ppm and corresponded to the methylene protons in (a). A multiplet for one proton was shown at 5.05 to 5.13 ppm, which corresponded to the methylene proton of (b).

From the above results, it was revealed that the isolated product was 3-chloro-1,2-dimethoxycarbonyloxypropane.

(Production of 3-chloro-2-methoxycarbonyloxy-1-propanol) The culture of the bacterium was 2.0
% Glucose, 1.0% Sucrose, 1.0% Meat Extract, 0.5% Peptone, 0.2% Yeast Extract, 0.3%
Sodium chloride, 0.4% potassium phosphate monobasic, 0.2
% Dibasic potassium phosphate, 0.1% magnesium sulfate-7
Add 500 ml of water salt, pH 7 medium to a 2 L shoulder flask and add Brevibacterium divaricatum 1627.
The NRRL 2311 strain was shake-cultured at 30 ° C. for 48 hours. After culturing, the supernatant was removed by centrifugation, and 50 mM phosphate buffer (pH 7.0) 50 was added under cooling.
Washed twice with ml. 250 mg of the obtained bacterial cells was added to pH 7
Disperse in 5 ml of 50 mM phosphate buffer adjusted to 3, add 3-chloro-1,2-dimethoxycarbonyloxypropane to 1% (weight / volume), and shake at 30 ° C. for 48 hours. Cultured. After the reaction, 5
Extraction was performed by adding ml of ethyl acetate.

When the extract was analyzed by column chromatography, the hydrolysis rate was 99.6%. The extract was concentrated and the residue was isolated and purified by thin layer chromatography to find that 35 mg (95.95%) of 3-chloro-2-methoxycarbonyloxy-1-propanol was obtained.
0%) was collected.

As a result of measuring the infrared absorption spectrum of this product, the absorption based on the carbonyl group at 1753 cm ^-1 was obtained.
Absorption based on hydroxyl groups was obtained at 3500 cm ^-1 . The elemental analysis values are C35.48%, H5.18%, C21.2
6%, which is a calculated value for the composition formula C ₅ H ₉ ClO ₄ (168.58), C35.62%, H5.38%, C
It was in good agreement with 121.03%. As a result of measuring a mass spectrum, a peak corresponding to M ⁺ was shown at m / e 168.

Further, the results of measurement of ¹ H-nuclear magnetic resonance spectrum (δ: ppm: tetramethylsilane standard; deuterated chloroform solvent) were as follows.

[0059]

[Chemical 6]

A broad singlet for one proton is shown at 3.10 ppm, which corresponds to the proton of the hydroxyl group in (e).
Multiple lines corresponding to four protons were shown at 3.50 to 3.74 ppm, which corresponded to the methylene protons of (a) and (c).
A singlet for three protons is shown at 3.82 ppm,
Corresponding to the methyl proton in (d). 4.95-5.0
A singlet for one proton is shown at 7 ppm, which corresponds to the methine proton in (b).

From the above results, it was revealed that the isolated product was 3-chloro-2-methoxycarbonyloxy-1-propanol.

Example 2 Brevibacterium divaricatum 1627 NRR
The strains shown in Table 1 were used in place of the L2311 strain,
The same operation as in Example 1 was performed. The hydrolysis rate after 48-hour culture was as shown in Table 1.

[0063]

[Table 1]

Example 3 (Synthesis of Substrate) The same operation as in Example 1 was carried out by using ethyl chlorocarbonate instead of methyl chlorocarbonate in Example 1. The obtained colorless transparent liquid was 0.2 Torr, 1
When vacuum distillation was performed at 28 ° C., 67.2 g (88%) of 3-chloro-1,2-diethoxycarbonyloxypropane was obtained.
%) Acquired.

As a result of measuring the infrared absorption spectrum of this product, an absorption based on a carbonyl group was obtained at 1749 cm ^-1 . The elemental analysis values are C42.28%, H5.88.
%, Cl 14.10%, and the composition formula is C ₉ H ₁₅ ClO.
C42.45 which is the calculated value for ₆ (254.67)
%, H 5.94%, Cl 13.92%.

As a result of measuring the mass spectrum, m
A peak corresponding to M ⁺ was shown at / e254.

Further, the ¹ H-nuclear magnetic resonance spectrum (δ: ppm: tetramethylsilane standard; deuterated chloroform solvent) was measured and the results were as follows.

[0068]

[Chemical 7]

A multiplet of 6 protons was shown at 1.29 to 1.35 ppm, which corresponded to the methyl protons of (f) and (g). A multiplet of two protons was shown at 3.68 to 3.80 ppm, which corresponded to the methylene proton of (c).
Multiple lines corresponding to four protons were shown at 3.68 to 3.80 ppm, which corresponded to the methylene protons of (d) and (e).

A multiplet of two protons was shown at 4.30 to 4.47 ppm, which corresponds to the methylene proton of (a). A multiplet for one proton was shown at 5.04 to 5.11 ppm, which corresponded to the methine proton in (b).

From the above results, it became clear that the isolated product was 3-chloro-1,2-diethoxycarbonyloxypropane.

(Production of 3-chloro-2-ethoxycarbonyloxy-1-propanol) 3-chloro-1,2
-Instead of dimethoxycarbonyloxypropane 3-
The same operation as in Example 1 was carried out using chloro-1,2-diethoxycarbonyloxypropane.

When the ethyl acetate extracted solution was analyzed by gas chromatography, its hydrolysis rate was 85.5%. The extract was concentrated, and the residue was isolated and purified by thin layer chromatography to give 3-chloro-2-
29m of ethoxycarbonyloxy-1-propanol
g (80.0%) was collected.

As a result of measuring the infrared absorption spectrum of this product, the absorption based on the carbonyl group at 1753 cm ^-1
Absorption based on hydroxyl groups was obtained at 3500 cm ^-1 . The elemental analysis values are C39.58%, H6.20%, C19.2.
5%, which is a calculated value for the composition formula C ₆ H ₁₁ ClO ₄ (182.60), C 39.47%, H 6.07%, C
It was in good agreement with 19.42%. As a result of measuring a mass spectrum, a peak corresponding to M ⁺ was shown at m / e 182.

Further, the result of measurement of ¹ H-nuclear magnetic resonance spectrum (δ: ppm: tetramethylsilane standard; deuterated chloroform solvent) was as follows.

[0076]

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A triple line corresponding to two protons was shown at 1.30 to 1.35 ppm and corresponded to the methyl proton of (e). A broad singlet for one proton was shown at 3.12 ppm, which corresponded to the proton of the hydroxyl group in (f). 3.62
Shows a multiplet of 4 protons at ˜4.13 ppm,
(A) Corresponds to the methylene proton of (c). 4.20
Shows a quartet for two protons at ~ 4.27 ppm,
Corresponding to the methyl proton in (d). 4.95-5.0
A singlet for one proton is shown at 5 ppm, which corresponds to the methine proton in (b).

From the above results, it was revealed that the isolated product was 3-chloro-2-ethoxycarbonyloxy-1-propanol.

Example 4 Brevibacterium divaricatum 1627 NRR
The strains shown in Table 2 were used in place of the L2311 strain,
The same operation as in Example 3 was performed. The hydrolysis rate after 48-hour culture was as shown in Table 1.

[0080]

[Table 2]

Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display area C12R 1:62) (C12P 7/62 C12R 1:15) (C12P 7/62 C12R 1:20) (C12P 7 / 62 C12R 1: 265) (C12P 7/62 C12R 1: 365)

Claims (3)

[Claims] 1. A compound represented by the following general formula (I): (R ¹ is an alkyl group.) A carbonate compound. 2. The following general formula (II): A dicarbonate compound represented by (R ² is an alkyl group). 3. The dicarbonate compound according to claim 2, which belongs to the genus Bacillus, genus Brevibacterium, genus Corynebacterium, genus Flavobacterium, genus Micrococcus, genus Xanthomonas, genus Nocardia, genus Rhodococcus, and acts on the dicarbonate compound according to claim 2. The carbonate compound according to claim 1, which is produced by causing a culture solution, a microbial cell or a treated product of a microorganism having the ability to produce the carbonate compound according to claim 1 to act on the dicarbonate compound according to claim 2. A method for producing a carbonate compound, comprising: