JPS61280296A - Biochemical production of optically active 2-(4-phenoxyphenoxy)propane-1-ol - Google Patents

Abstract

PURPOSE:To obtain the titled compound having high optical purity and the ester of its antipode, by the asymmetric hydrolysis of a specific optically in active compound with an esterase produced by a microbial strain. CONSTITUTION:A 1-18C organic carboxylic acid ester of the optically inactive dl-2-(4-phenoxyphenoxy)propane-1-ol is subjected to the asymmetric hydrolysis with an esterase produced by a microbial strain to obtain an optically active 2-(4-phenoxyphenoxy)propane-1-ol having high optical purity and an ester of its antipode. The 2-(4-phenoxyphenoxy)progane-1-ol of formula I is an intermedi ate for the novel ether compound of formula II having the activity to control noxious life. The microbial strain is preferably those belonging to Chromobacterium genus or Arthrobacter genus to attain high optical purity.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a biochemical optical resolution method for (±)-2-(4-phenoxyphenoxy)-propan-1-ol represented by the following formula (1). More specifically, esterase produced by microorganisms is an organic carboxylic acid (with 1 carbon number) of (±)-2-(4-phenoxyphenoxy)propan-1-ol.
Asymmetric hydrolysis of ~18 saturated or unsaturated carboxylic acid esters produces optically active 2-(4-phenoxyphenoxy)propan-1-ol and its enantiomer ester with high optical purity. Industrially advantageous 2-(4-phenoxyphenoxy)propane-1 by obtaining
-Relating to a biochemical optical resolution method of ol.

PRIOR ART AND PROBLEMS 2-(4-phenoxyphenoxy)propan-1-ol represented by the above formula (1) is a novel ether compound represented by formula (I)C which has excellent pest control activity, for example. It is an important intermediate of

The ether compound represented by the above formula (1) can be mixed into feed or drinking water for livestock or poultry, fed to livestock or poultry, or administered orally to remove the active ingredient from their excretion. It is a very useful compound especially for public health, as it can exterminate flies that grow in excrement or compost caused by excrement.

Since the ether compound represented by the above formula (1) has one asymmetric carbon, two types of optical isomers exist. Among them, the ether compound having (S)-configuration is (R)
-The optically active 2-(4-F) represented by the general formula (1) as a synthetic intermediate has approximately 4 times the activity (eclosion inhibition activity in house flies) compared to the It would be desirable to develop an advantageous method for obtaining enoxyphenoxy)propan-1-ol.

A general method for obtaining optically active 2-(4-phenoxyphenoxy)propan-1-ol is to convert optically active lactic acid into ethyl ester, and then react with p-toluenesulfonic acid chloride to form tosyl ester. Conceivable methods include reacting with phenoxyphenol under alkaline conditions to obtain optically active ethyl ester of 2-(4-phenoxyphenoxy)propionic acid, and further reducing this with lithium aluminum hydride.

However, such a method requires a long number of steps and requires the use of an expensive optically active raw material, which is disadvantageous for industrial implementation.

Structure of the Invention Under these circumstances, the present inventors have developed an industrially advantageous (
±)-2-(4-phenoxyphenoxy)propane-1
-As a result of repeated research to establish an optical resolution method for oars,
By allowing the esterase derived from the following microorganism to act on the organic carboxylic acid (saturated or unsaturated organic carboxylic acid having 1 to 18 carbon atoms) ester of (±)-2-(4-phenoxyphenoxy)propan-1-ol. Optically active 2-(4-phenoxyphenoxy) with extremely high optical purity
It was discovered that esters of -propan-1-ol and its enantiomer can be obtained, and various studies were conducted to complete the present invention.

Next, the present invention will be explained in detail.

(i:)-2 used as raw material in the method of the present invention
The organic carboxylic acid (saturated organic carboxylic acid having 1 to 18 carbon atoms) ester of -(4-phenoxyphenoxy)propan-1-ol can be produced using a column method for ester production, such as (±)-2-(4 It can be easily produced by reacting -phenoxyphenoxy)propan-1-ol with an anhydride of an organic carboxylic acid, or by reacting an organic carboxylic acid chloride in the presence of an organic base.

The microorganism that produces the esterase used in the present invention includes an esterase (herein, Esterase is a microorganism that produces esterase in a broad sense including lipase.Specific examples include Pseudomonas X, Chromobacterium, Arthrobacter, and Alcaligenes. ) genus, Candida genus, Achromobacter (Ac
hromobacter genus, Nocardia (Noca
rdia), Flavobacterium (F1avot)
+acterium genus, Tolulopsis
psi) f4, Brevibacterium (Brev-
ibacterium) 5%, B
acillus), Niskelisif (Escheri)
chia) f4, Micrococcus
occus) genus, Hansenula
Genus Mucor, Genus Corynebacterium, Genus Zcobacterium, Genus Sac-charomyces, Genus Thermomyces (Humicola) a)) Genus Rhizopus ( Rh1zopu
s) genus, Aspergillus
Genus, Streptomyce x
s) genus, Geotricum genus, Trichoderma genus, Acinetobacter genus, Aeromona:
Beauveria), Rhodotorula (Rhod-ot)
orula), Enterobacter (Enterobacter)
cter) genus, Penicillium
Genus, Serratia genus, x ruby = 7
(Erwinia) genus, Staphylococca x (S
taphylococcus), Hycomyces (P
hycomyces), Propionibacterium (
genus Propionibacterium, genus Metarhizium, genus Paec-ilomyces, genus Saccaro-mycopsis, genus Verticil-1ium,
Examples include microorganisms belonging to the genus Xanthomonas.

Representative strain names belonging to each of these genera are illustrated below, but the microorganisms of the present invention are not limited to these examples.

(1) Nocardia erythropolis (Nocar
diaerythropolis) I
F 0-12682 and IFO-12820 (2) Arthrobacter simplex (Art
-hrobacter simplex) I
FO-12069 (8) Flavobacterium arborescens (Flav-obacterium a
rborescens) IFO-8750 (4
) Torulopsis candida
candida) I FO-08
80 (ω Brevibacterium ammoniagenes (B
re-vivacterium ammonium
es) IFO-12072 (6) Bacillus
Bacillus li-chen
iformis) IFO-121
97(7) Batil X' X 7 z Rika X (B
acillus 5pha-elicus)
I FO-8528 (8) Escherichia coli IF
O-8801 (9) Hansenula Sachis JL/Han
senula saturnus)
I FO-011700) Micrococcus varians
I FO-8765 (11) Chromobacterium viscosum
ium viscosum) ATCC-6
918(12) Pseudomonas fluorescens
) IFO-8081 (1i3) Arthrobacter ureafaciens (Art-hroba
cter ureafaciens) ATCC-
7562 (14) Alkaligene X-Fakeli x (A
lcaligenes faecalis)
IFO-12669 (15) Candida utilis IFO-
0988 (16) Achromobacter species (Achrom)
obac-ter, genus s)
ATCC-21910 (17) Mukhor Bushira x
(Mucor pusillus) IFO-9856 (18) Corynebacterium glutamicum (Cory
-nebacterium glutamicum)
ATCC-18287(19)F,-1 Bacterium
Fly (Mycobac teriumphlei)
IFO-3153 (2o) Saccharomyces saccharo-my
ces cerevisiae) ATCC-
7753 (21) Sacc-haromyces carlsb
ATCC-9080 (22)
? −%? Ises lanuginosus (Thermomyce)
slanuginosus) I F
O-9788 (Humicola lanuginosa, Humico
la lanugi-nosa) (28) Rhizopus X-japonica x
japon-icus) I
FO-4758 (24) 7 Supergillus oryzae (A
spergi 1lus-oryzae)
ATCC-14605 (25) Aspergi 1lusflavus
) ATCC-11492(26)
Streptomyces griseus subs.
ceus 5u-bs, griseus)
IFO-23480 (27) Streptomyces kasugaensis
yces kaaugaensis) I F
O-18851 (28) Geotricum candidum
I FO-4597 (29) ) Trichoderma viri-de
) IFO-5720 (3
0) Acinetobacter calcoaceticus (Acine
t-obacter calcoaceticus)
IFO-12552 and IFO-18006 (81) Aeromonas hydrophila subspecies - Hydrophila
genus drophi 1asubs, 1xydrophi
la) I FO-12978 (32) Beauveria bass-
iana) ATCC-26
087 (83) Rhodotorula m1nuta va
r, texensis) IFO-0879 (84) Enterobacter aeromonas (Ent.
er-obacter aerogenes)
i FO-18584 (85) Penicillium canescen: x, (Penicillium canescen
s) IFO-7108(8
6) Serrati y -v lucescens (Serrati
a marc-escens)
I FO-12648 (87) Erwinia carotovora Subspecies carotovora (Erwini)
a carotovora 5ubsp.

carotovora) I FO
-14082 (88) Staphylococcus aureus
I FO-8060 (89) Phycomyces nitae: /
ens) IFO-9422 (40
) Propionibacterium acnes (Pro-pio
nibacterium acnes) ATCC
-11827(41) Metarrhizium-72'/Metarrhiziumanisopliae
ATCC-16085 (42) Xanthomonas oryzae
yzae) I FO-8812(
48) Saccharomycopsis lipolytica (Sac-c
haromycopsis 1ipolytica)
ATCC-84088 (44) Verti-cilium fungic
ola) i FO-80616 (45) Paecilomyces lilacinus (Paecilom-yce
s 1ilacinus) ATCC-18
807 All of these strains are American Ty
pe Cu1-ure Co11ection (ATC
C) or preserved at Osaka Fu's Institute of Fermentation (IFO), and can be obtained from these preservation institutions.

Furthermore, some of these microbial-derived esterases are commercially available and can be easily obtained. Specific examples of commercially available esterases include Pseudomonas lipase (manufactured by Amano Pharmaceutical) and Mucor lipase (manufactured by Amano Pharmaceutical Co., Ltd.).
Lipase M-AP (manufactured by Amano Pharmaceutical Co., Ltd.), Cantype Cylindrace lipase (Lipase MY (manufactured by Meito Sangyo Co., Ltd.)
), alkaline earth metal lipase (Lipase PL (Meito Sangyo)), Achromobacter lipase (Lipase AL (Meito Sangyo)), Arthrobacter lipase (Lipase Joint BSL (Joint Sake Refining)) Similarly, lipase of the genus Arthrobacterium (manufactured by Shin Nippon Kagaku Kogyo), lipase of the genus Chromobacterium (manufactured by Toyo Jozo), lipase of the genus Rhizopus (Lipase Saiken 100 (manufactured by Osaka Bacteria Research)), etc.

In the esterases derived from microbial sources as mentioned above,
When carried out on an industrial scale, Pseudomonas spp.
Mucor genus, Chromobacterium (Ch
romobacterium), Escherichia (E
scherichia), Arthrobacter (Ar
t-hrobacter) genus, alkaline earth X (Al
genus Bacillus caligenes, Bacillus
) genus, Nocardia genus, Candida genus, Achromobacter (Ach
romobacter), Flavobacterium (Fl
avobacterium), Brevibacterium (B
revibacterium), Krokotsucus (M
icrococcus) FJ, Torulobushi x (To
lulops-is), Hansenula
la) genus, Acinetobacter (Acinetobacter)
ter) Jji, Aeromona
s), Rhodotorula, Trichoderma, Geotricum, Be
auveria), Streptomy-1! X (S
treptomyces), Mycobacterium (My
cobacterium), Satucharomyces (S
accharomyces), Aspergillus (A
Esterases produced by microorganisms belonging to the genus Spergillus are more preferred. Furthermore, Chromobacterium (Chr-omoba) provides even higher optical purity.
cterium) genus, 7') Ll S0 bacter (A
Esterases produced by microorganisms belonging to the genus Rth-robacter are more preferred.

In the method of the present invention, the microorganism that produces the esterase used is usually cultured by performing liquid culture according to a conventional method to obtain a culture solution.

For example, a sterilized liquid medium [for molds and yeasts frequently used, malt extract/yeast extract medium (11 parts water to 5 parts Buffton,
Dissolve 1 o, oy of soluble starch, 8.0 g of malt extract and 8.0 g of yeast extract and adjust the pH to 6.2),
For actinomycetes, sterile liquid medium (10.0% soluble starch in 111% water), NZ amine (type A)2. Q, meat extract 1. of! and yeast extract 1. Dissolve Of;
For bacteria, use a sterilized liquid medium (dissolve 10.0 of soluble starch, 5.0 of peptone, and 5.0 of yeast extract in 11.0 of water to give a pH of 6.8).
The microorganisms are incubated and cultured with reciprocating or rotary shaking, usually at 20 to 40°C for 1 to 8 days. Further, solid culture or anaerobic culture may be performed as necessary. Furthermore, during such culture, enzyme production can be improved by adding natural oils and fats such as olive oil and soybean oil, and nonionic surfactants such as polyoxyethylene sorbitan monooleate to the medium as inducers. You can also do it.

The asymmetric hydrolysis of organic carboxylic acid (saturated or unsaturated carboxylic acid having 1 to 18 carbon atoms) ester of (±)-2-(4-phenoxyphenoxy)propan-1-ol in the method of the present invention is as described above. Culture medium in which microorganisms are cultured, bacterial cells isolated from the culture liquid, and culture P containing esterase
Bacterial cells or culture F using liquid or various enzyme separation methods
Crude esterase separated from the liquid, purified esterase, esterase-containing extract, or concentrated liquid
This is carried out by mixing 2-(4-phenoxyphenoxy)propan-1-ol with an organic carbodiic acid ester and stirring or shaking the mixture. It is also possible to use immobilized bacterial cells or immobilized esterase.

As conditions for performing asymmetric hydrolysis, the reaction temperature is 10~
70°C is appropriate, and for thermostable esterase obtained from thermophilic bacteria culture or thermophilic bacteria culture, the temperature is 60 to 65°C.
20 to 50°C is preferable for a culture solution of a mesophilic bacterium or an esterase that does not have particular heat resistance.

The reaction time is usually 8 to 70 hours, but the reaction time can be shortened by raising the reaction temperature or increasing the amount of enzyme.

The pH during the reaction is 8-11. For culture solutions of microorganisms that are not alkaliphilic or for esterases that are not alkali tolerant, pH 5 to 8 is preferred.

Further, in order to neutralize the organic carboxylic acid produced by hydrolysis and to keep the pH constant during the reaction, it is preferable to use a buffer solution or to drop an alkaline aqueous solution as the reaction progresses.

Examples of the buffer include a mild solution of inorganic ferment salts such as sodium phosphate and potassium phosphate, and buffer solutions of organic ferment salts such as sodium acetate and sodium citrate.

Substrate (±)-2-(4-phenoxyphenoxy)
The concentration of the organic carboxylic acid ester of propan-1-ol is 0.5 to 80% by weight based on the reaction solution, and preferably 10 to 60% by weight in industrial implementation.

In addition, in the organic carboxylic acid ester of (-1z)-2-(4-phenoxyphenoxy)propan-1-ol, which is a raw material, the organic carboxylic acid has 2 to 12 carbon atoms from the viewpoint of ease of handling and reactivity. Carboxylic acids are preferred, and acetic acid is more preferred in terms of economy and availability.

Next, after performing the asymmetric hydrolysis reaction in this manner, the liberated optically active 2-(4-phenoxyphenoxy)propan-1-ol and the unreacted enantiomer ester are separated and recovered. During this separation and recovery, solvent extraction, fractional distillation,
Operations such as column chromatography and recrystallization can be employed as appropriate. For example, the reaction solution is extracted with an organic solvent such as ether, ethyl acetate, or benzene, and the extract is fractionally distilled to separate and obtain optically active 2-(4-phenoxyphenoxy)propan-1-ol and its enantiomer ester. or subject the extract to column chromatography on silica gel, e.g. hexane-ethyl acetate (
5:1) By elution with a solution, the optically active 2-
The organic carboxylic acid ester of (4-phenoxyphenoxy)propan-1-ol was separated and then eluted with a hexane-ethyl acetate (2:1) solution to release the free 1-( 4-phenoxyphenoxy)propan-2-ol is separated.

Furthermore, the optically active 2-(4-
The ester of phenoxyphenoxy)propan-1-ol can be easily converted to optically active 2 by further hydrolysis.
-(4-phenoxyphenoxy)propan-1-ol. As a method for hydrolysis, for example, an organic carboxylic acid ester of optically active 2-(4-phenoxyphenoxy)propan-1-ol is added to a solution of caustic soda or caustic potassium in water, methanol, or ethanol, and the mixture is heated in a room! By stirring at (20°C to 80°C), optically active 2-(4-phenoxyphenoxy)
Propan-1-ol can be taken.

Moreover, optically active 1't2-(4-phenoxyphenoxy)propan-1-ol obtained from the ester of optically active Fl-(4-phenoxyphenoxy)propan-1-ol by the above method has insufficient optical purity. In some cases, it is possible to obtain 2-(4-phenoxyphenoxy)propan-1-ol with high optical purity by increasing the reaction time of asymmetric hydrolysis and increasing the ice melting rate (at least 60% or more). I can do it.

Effects of the Invention According to the method of the present invention, optically active 2-(4-phenoxyphenoxy)propan-1-ol can be obtained in high yield and optical purity, which is extremely advantageous from an industrial perspective.

Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.

Example 1 (±)-2-(4-phenoxyphenoxy)-propyl acetate 5°OOf (17.5 mmol) Chromobacterium lipase (manufactured by Toyo Jozo Co., Ltd.) 15011& was added to phosphate buffer at a concentration of 0.2 M liquid (pH (i, 8)
15 ml and reacted at 40°C with stirring.

At this time, as the reaction progresses, IN caustic soda solution is added and p
H was maintained at 6,8. After reacting for 5 hours, the reaction product was extracted with toluene. The extract was analyzed by gas chromatography (Color A: 5ilicon DC-QF-12°5m, galam column. Column temperature = 280°C), and the results showed that 2-(4-phenoxyphenoxy)-1-propyl acetate: 70.6 %, 2-(4-phenoxyphenoxy)propan-1-ol: 29.4%, no other components were observed.

The extract was then reduced to zero and subjected to column chromatography packed with silica gel to obtain 8.58 g of 2-(4-phenoxyphenoxy)-1-propyl acetate.
and 2-(4-phenoxyphenoxy)propane-1-
All 1.251 Specific optical rotation: [α), = f32.70 (
Chloroform, c=i,oo)) was obtained.

The 2-(4-phenoxyphenoxy)propan-1-ol obtained here was subjected to liquid chromatography using an optically active column (Color A: Sumipax OA-
As a result of optical isomer analysis using 2300 (manufactured by Sumika Analytical Center Trowel), S-(+) unitary/R-(-) unitary = 95.
It was 015.00.

Example 2 The same procedure as in Example 1 was carried out except that the amounts of (+)-2-(4-phenoxyphenoxy)-1-propyl acetate and lipase used were doubled and the reaction time was changed to 4 hours. Made it react. After the reaction, the reaction solution was treated in the same manner as in Example 1 and analyzed by gas chromatography.
As a result of analysis, 2-(4-phenoxyphenoxy)-1
-probyl acetate di-75.0%, 2-(4-phenoxyphenoxy)propan-1-ol: 25.0%.

The reaction solution was then treated in the same manner as in Example 1 and subjected to silica gel chromatography to obtain 2-(4-phenoxyphenoxy)propan-1-ol 2.181 (S
-(+)integral/R-C-')integrated=97.5/
2.5 Specific light intensity = Ca] A' = a 4.40 (
rioo*rum, (,= 1.Oo)2'/ji'
;! .

Example 8 Arthrobacter ureafaciens (Arthro
bacter ureafaciens) (ATCC-
7562) to obtain a strain with high enzyme production by selecting colonies exhibiting high enzyme productivity. Using a 51-capacity minijafermenter, the thus obtained highly enzyme-producing strain of Arthrobacter ureafaciens was incubated at 80°C by adding soybean meal extract and 2% olive oil to a normal bacterial culture medium.
Aerated culture was performed for 81 hours (Culture solution 31).

After removing the bacterial cells by centrifugation, the culture solution was subjected to solvent precipitation with acetone (fractionation between 255% acetone and 80% acetone), the precipitated enzyme protein was separated by centrifugation, and then freeze-dried. A dry enzyme of t O,6y was obtained.

The thus obtained dried enzyme 1°Of and (±)-2-(4
-phenoxyphenoxy)-1-propylcabrilate 40F in 0°IM concentration of phosphate buffer (pH 6,8)
The mixture was added to 180 mg/ml and reacted at 48°C with stirring. At this time, as the reaction progressed, 2N caustic soda solution was added to maintain the pH at 6.8 during the reaction.

After reacting for 8 hours, the reaction product was extracted with toluene.

The extract was analyzed by gas chromatography under the same conditions as in Example 1. As a result, 2-(4-phenoxyphenoxy)propan-1-ol: 85.0%, 2-(4-phenoxyphenoxy)-1-probyl caprylate 265゜0
%Met.

The extract was then chromatographically separated as in Example 1 to give 2-(4-phenoxyphenoxy)
Propan-1-ol 9.219 (S-(+) unit/R-C-') unit = 90.5/9.5) was obtained.

Example 4 In Example 8, (±)-2-(4-phenoxyphenoxy)-1-propylcabrilate was replaced with (±)-
The reaction was carried out under the same conditions as in Example 3, except that 2-(4-phenoxyphenoxy)-1-propylpropionate was used and the reaction scale was set to 175. The reaction solution was treated in the same manner as in Example 1, and then analyzed by gas chromatography. As a result, 2-(4-phenoxyphenoxy)
Propan-1-ol: 40.2%, 2-(4-phenoxyphenoxy)-1-propylpropionate = 69
．． It was 8%.

The reaction solution was subjected to chromatography in the same manner as in Example 1, and 2-(4-phenoxyphenoxy)propane-1-
A total of 2.61 fI (5-(+) integral/R-(-) integral = 88.5/11.5) was obtained.

Examples 5-14 (±)-2-(4-phenoxyphenoxy)-1-F0
0.5 f (1,75 t remol) and each enzyme shown in Table 1 (the amounts used are shown in Table 1).
．． Phosphate buffer with a concentration of 2M (pI (e, s) 20
ml was added, and a hydrolysis reaction was carried out with stirring at 40"C (reaction times are shown in Table 1). The reaction solution was treated in the same manner as in Example 1, and the hydrolysis rate and the product obtained by the hydrolysis reaction were determined. The ratio of S-(+) and R-(-) of the optically active 2-(4-phenoxyphenoxy)propan-1-ol obtained was measured.

The results are shown in Table 1.

Table 1 Examples 12-29 600-proof Erlenmeyer flask Iζ liquid medium [For bacteria, 10% soluble starch in 11% water. Of.

Peptone 560f and cod extract 5. Dissolve Ol,
The pH was adjusted to 6.8. For frequent use of yeast, add 10 parts of soluble starch to 11 parts of water. Of, Peptone 5, Of, 9 Bud Extract 8
゜Of and yeast extract 8, dissolve Of, pH 6,
2. For actinomycetes, 10% soluble starch in 11% water. Of.

NZ Amine-Type A” 2°Of, Meat Extract 1,Of
After adding 100g of yeast extract (1°Og of yeast extract to pH 7.2) and sterilizing it, each microorganism listed in Table 2 was inoculated with a platinum loop from a slant culture,
Rotary shaking culture was carried out for 60 hours. Then add (±')-2 to this
2.0 f (6.99 mmol) of -(4-phenoxyphenoxy)-1-propyl acetate was added, and a hydrolysis reaction was carried out for the time shown in Table 21ζ while stirring at 80°C.

Thereafter, extraction, separation, and analysis were carried out in the same manner as in Example 1 to determine the hydrolysis rate and the S-(trifluorol) of optically active 2-(4-phenoxyphenoxy)propan-1-ol obtained in the hydrolysis reaction. ) unite and R-(he) unite ratio was measured. The results are shown in Table 2.

! 1!2 Example 80 (±)-2-(4-phenoxyphenoxy)-1-propyl acetate 8.00f (28.0 mmol) and Chromobacterium lipase (Toyo Jozo) 0.25
F in 0.2M phosphate buffer (pH 6,8) 2
In addition, the mixture was added to 100 ml of water and reacted at 40° C. with stirring. At this time, as the reaction progresses, IN caustic soda solution is added to adjust the pH to 6.
．． It was held at 8. After reacting for 40 hours, the reaction product was extracted with toluene. The extract was analyzed by gas chromatography in the same manner as in Example 1. :MJL 2-(4-phenoxyphenoxy)-1-propyl acetate: 40°9%, 2-(4-phenoxyphenoxy)propane-1
-All: 59.1%, and no other components were observed.

The extract was then concentrated and subjected to column chromatography packed with silica gel to obtain 8.27f of 2-(4-phenoxyphenoxy)-1-propylacetate.

Of these, 1.0y was dissolved in a 5.86N methanol solution of caustic potassium (concentration 10%) and stirred at 20°C for 1 hour. The reaction solution was diluted with 100 ml of water, extracted with toluene, and the resulting toluene layer was concentrated to obtain 2-
(4-phenoxyphenoxy)propan-1-ol 0
．． Obtained 85F.

As a result of optical isomer analysis of the 2(4-phenoxyphenoxy)propan-1-ol in the same manner as described above, S-(t)integral/R-(→integral=0.8/99.2 (ratio) Light intensity [0 yuan”' 85.7° (chloroform,
C=1, QO).

Claims (1)

[Claims] (1) Pseudomonas genus,
Chromobacterium
) genus, Arthrobacter
Genus, Alcaligenes, Candida, Achromobacter (
Achro-mobacter) genus, Nocardia (N
ocardia), Flavobacterium (Flavo
bacterium genus, Tolulopsis
psis), Brevibacterium (Brevibac
terium) genus, Bacillus genus,
Escheric-hia spp., Micrococcus spp., Hansenula spp.
Hansenula genus, Mucor (Muc-or) genus, Corynebacterium (Corynebacterium)
um) genus, Mycobacterium (Mycobacterium)
ium), Saccharomyces
-ces) genus, Thermomyces
s) (Humicola) genus, Rhizopus (
Genus Rh-izopus, Aspergillus
gillus), Streptomyces (Strept.
omyces), Geotricum
), Trichoderma, Acinetobacter, Aeromonas, Beauveria (
Genus Beauveria, Rhodotorula
rula genus, Enterobacter
ter) genus, Pen-icllium
Genus, Serratia, Erwinia (E
rwinia), Staphylococcus (Staphy
lococcus), Hycomyces (Ph-ycom)
yces), Propionibacterium (Propio
genus nibacterium, Metarhizium
rrhizium), Paecilomyces (Paeci)
lomyces), Saccharomycopsis (Sacca)
romycopsis), Veerticillium (Ve
rticillium), Xanthomonas (Xan-
The esterase produced by microorganisms belonging to the genus (±)-2-(4-phenoxyphenoxy)propan-1-ol (carbon number 1-18) is
2-(4-phenoxyphenoxy)propan-1-ol and its enantiomer ester by asymmetric hydrolysis. It is characterized by (±
)-2-(4-phenoxyphenoxy)propane-1-
Biochemical optical resolution method for all. (2) Pseudomonas genus,
Mucor genus, Chromobacterium (Ch
r-omobacterium), Escherichia (E
scher-ichia), Arthrobacter (Ar
throbac-ter) genus, Alcaligenes (Alc
genus Bacillus
Genus, Nocardia, Candida, Achromobacter
omobacter) genus, Flavobacterium (Fla
vobacterium), Brevibacterium (Br
evibacterium), Micrococcus (Mi
crococcus genus, Tolulopsis
psis), Hansenula genus,
Acinetobacter genus,
Aeromonas spp., Rhodotorula (
Genus Rhodotorula, Trichoderma
genus Hode-rma, Geotrichum
A patent claim using an esterase obtained from a microorganism belonging to the genus Um, Beauveria, Streptomyces, Mycobactrium, Saccharomyces, and Aspergillus. The method described in paragraph 1 of the scope. (8) Chromobacterium
ium), Arthrobacter
The method according to claim 1, which uses an esterase obtained from a microorganism belonging to the genus Er).