CN110699278A - Application of whole cells of bacillus DL-1 in catalytic resolution of styracin acetate - Google Patents
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Abstract
The invention discloses application of a whole cell of bacillus DL-1 in catalytic resolution of styracin acetate. The bacillus DL-1 whole cell can be used as a catalyst for preparing chiral (R) -1-phenylethylalcohol and (S) -styrofol acetate with high optical purity. Under the optimal reaction condition, the enantiomer excess value of (R) -1-phenethyl alcohol obtained by carrying out full-cell catalytic resolution on (+/-) -styroform acetate by using bacillus DL-1 is 96.6%, the conversion rate is 24.5%, and the yield is 48.1%; the catalytic resolution of (+/-) -styryl acetate can obtain (S) -styryl acetate with enantiomeric excess of 98.4%, conversion rate of 56.6% and yield of 86.2%. The whole cell of the bacillus DL-1 is used as a biocatalyst, has higher substrate tolerance and optical selectivity in the reaction of chiral resolution (+/-) -styroform acetate, and has greater application value in the field of biochemical engineering.
Description
Technical Field
The invention belongs to the fields of biochemical engineering and biotechnology, and particularly relates to application of a whole cell of bacillus DL-1 separated from a sample of a western pacific deep sea sediment as a biocatalyst in catalytic resolution of styrallyl acetate.
Background
Whole-cell catalysis refers to chemical transformations that utilize intact biological organisms (i.e., whole cells, tissues, or even individuals) as catalysts, which in essence catalyze the transformation with intracellular enzymes. The advantages of using a whole-cell biocatalyst are: firstly, enzyme extraction and purification are not needed, enzyme activity loss is reduced, the preparation is simple, and the production cost is greatly reduced; secondly, the stability of the whole-cell biocatalyst in repeated use can be enhanced by culturing in an anhydrous or unconventional medium; and thirdly, the in-situ regeneration of energy and coenzyme can be realized, and the complete multi-enzyme system can realize the enzyme cascade reaction. The whole-cell catalysis technology is bound to become the core of the whole biological catalysis technology due to the advantages of the whole-cell catalysis technology. Chiral alcohol is used as an important intermediate for synthesizing chiral drugs, and has wide application in the pharmaceutical field at present. The traditional chemical synthesis of chiral alcohol and its derivatives has the problems of expensive reagents, harsh reaction conditions, high cost, large pollution and the like. The preparation of chiral alcohols using whole cells as biocatalysts shows its unique advantages.
Disclosure of Invention
The invention aims to provide a bacillus sp.DL-1 separated from western Pacific ocean deep sea sediments and application of a whole cell of the bacillus serving as a biocatalyst in catalyzing (+/-) -styroform acetate asymmetric hydrolysis to prepare (R) -1-phenethyl alcohol and (S) -styroform acetate with high optical purity.
The first purpose of the invention is to provide a marine-derived Bacillus sp.DL-1 which can be used for asymmetric ester hydrolysis. The preservation number of the Bacillus sp.DL-1 is as follows: GDMCC 1.1696.
The Bacillus sp.DL-1 is derived from deep sea sediments of the western pacific ocean, and the nucleotide sequence of 16S rRNA is shown as SEQ ID NO. 1.
The second purpose of the invention is to provide the application of the whole cell of Bacillus sp.dl-1 in catalyzing the asymmetric hydrolysis of (+/-) -styroformate acetate.
In particular to application of a whole cell of Bacillus sp.DL-1 in catalytic resolution of (+/-) -styrofol acetate to obtain (R) -1-phenethyl alcohol.
And providing the application of the whole cell of the Bacillus sp.DL-1 in the catalytic resolution of (+/-) -styroform acetate to obtain (S) -styroform acetate.
The whole cell of the Bacillus sp.DL-1 can be used as a biocatalyst to asymmetrically hydrolyze (+/-) -styrofol acetate to prepare (R) -1-phenethyl alcohol and (S) -styrofol acetate with high optical purity.
The whole cell of the Bacillus sp.DL-1 needs to be fermented and cultured for about 24 hours by using a defatted milk powder liquid culture medium, the supernatant is centrifuged, and the cell precipitate is washed three times by using a sterile Tris/HCl buffer solution with the pH value of 7.2.
The optimal reaction conditions for obtaining (R) -1-phenethyl alcohol by the whole-cell catalytic resolution of (+/-) -styrofol acetate of the Bacillus sp.DL-1 are as follows: the reaction system comprises bacillus DL-1 with cell concentration of 48mg/mL based on cell wet weight, 50mM substrate (+/-) -styroform acetate, methanol with volume fraction of 5%, and the balance of PB buffer solution with pH of 6.0; the reaction temperature is 40 ℃ and the reaction time is 0.5 h.
The enantiomeric excess (e.e) of the (R) -1-phenylethyl alcohol prepared under the above-mentioned optimum reaction conditions.p) 96.6%, conversion 24.5%, yield 48.1%.
The optimal reaction conditions for obtaining (S) -styryl acetate by carrying out whole-cell catalytic resolution on (+/-) -styryl acetate by using Bacillus sp.DL-1 are as follows: the reaction system comprises Bacillus sp.DL-1 with the cell concentration of 60mg/mL based on the wet weight of the cells, 50mM substrate (+/-) -styroform acetate, acetone with the volume fraction of 5%, and the balance of PB buffer solution with the pH value of 6.0; the reaction temperature is 35 ℃ and the reaction time is 5 h.
The enantiomeric excess (e.e) of the (S) -styrofoam acetate prepared under the above-described optimal reaction conditions.s) 98.4%, conversion 56.6%, yield 86.2%.
The invention utilizes the whole cells of Bacillus sp.DL-1 as a biocatalyst to have higher substrate tolerance and optical selectivity in the reaction of chiral resolution (+/-) -styrofol acetate. The green and low-cost Bacillus sp.DL-1 whole-cell biocatalyst has great application value in the field of biochemical engineering.
The Bacillus sp.DL-1 is preserved in Guangdong province microorganism culture collection (GDMCC) in 2019, 8 and 20 months, wherein the preservation number is GDMCC1.1696, and the address of the preservation unit is as follows: no. 59 building No. 5 building of No. 100 college of Pieli Zhongway, Guangzhou city, anyone could purchase the strain to the collection before the filing date.
Drawings
Fig. 1 is a growth curve of Bacillus sp.dl-1.
FIG. 2 is a gas chromatogram of a (+/-) styrofol acetate and a (+/-) -1-phenylethyl alcohol standard.
FIG. 3 is a gas chromatogram of selective hydrolysis of styrofol (. + -.) acetate by Bacillus DL-1 whole cells under optimal reaction conditions to produce (R) -1-phenylethyl alcohol with high optical purity.
FIG. 4 is a gas chromatogram of selective hydrolysis of (+/-) styrofol acetate by Bacillus DL-1 whole cells under optimal reaction conditions to obtain highly optically pure (S) -styrofol acetate.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof.
The Bacillus sp.DL-1 is obtained by screening from western Pacific ocean deep sea sediments and is stored in a biological catalysis laboratory of the south China sea institute of sciences.
Example 1: identification of Bacillus species
And (3) identifying the strains of the screened and purified strain Bacillus sp.DL-1 by using the conserved 16S rRNA sequence. With 16S rRNA universal primer 27F: 5'-AGAGTTTATCCTGGCTCAG-3', respectively; and 1492R: 5'-GGTTACCTTGTTACGACTT-3', PCR amplification is carried out using Bacillus DL-1 bacterial liquid as DNA template. The reaction system shown in table 1 was set up:
TABLE 1 PCR reaction System
PCR amplification conditions: pre-denaturation at 94 deg.C for 10min, denaturation at 94 deg.C for 30s, annealing at 56 deg.C for 30s, and extension at 72 deg.C for 2min for 30s, and circulating for 30 times; finally, the extension is carried out for 10min at 72 ℃ and the temperature is cooled to 18 ℃. The amplification product was subjected to 1% agarose gel electrophoresis, detected, and then sent to Meiji Biotechnology Ltd for bidirectional sequencing. After the 16S rRNA sequence of the strain is obtained and spliced (the nucleotide sequence is shown as SEQ ID NO. 1), the strain is identified to be Bacillus by utilizing BLAST and is named as Bacillus sp.DL-1. The Bacillus sp.DL-1 is preserved in Guangdong province microorganism culture Collection (GDMCC) in 2019, 8 and 20 months, wherein the preservation number is GDMCC1.1696, and the address of the preservation unit is as follows: guangzhou city, first furious Zhonglu No. 100 large yard No. 59 building No. 5.
Example 2: growth curve of Bacillus sp.DL-1
The preserved Bacillus sp.DL-1 is streaked on an LB solid culture medium (1% tryptone, 0.5% yeast powder, 1% NaCl, 1.5% agar powder and water as a solvent in mass fraction), cultured at 37 ℃ for 16h, then a single colony is selected and inoculated into 100mL of an LB liquid culture medium (1% tryptone, 0.5% yeast powder, 1% NaCl and water as a solvent in mass fraction), cultured at 200r/min and 37 ℃ for 12h to obtain a seed solution, the seed solution is inoculated into the LB liquid culture medium according to the inoculum size of 1% v/v for culture, cultured at 200r/min and 37 ℃, and the biomass OD-600nm is measured every 2h, and the result is shown in figure 1.
Example 3: preparation of Bacillus sp.DL-1 Whole cell
Inoculating the seed solution of Bacillus sp.DL-1 into a defatted milk powder liquid culture medium (10 g of high-protein defatted high-calcium milk powder (purchased from Yili, Inc., of inner Mongolia industries, Ltd.) is dissolved in 1L of water, sterilized at 115 ℃ for 30min and cooled) for fermentation culture, culturing at 200r/min and 37 ℃ for 24h (the culture medium becomes clear) to obtain a fermentation liquid, centrifuging to remove a supernatant, washing cell precipitates for three times by using a Tris/HCl buffer solution sterilized at the pH of 7.2, and centrifuging to collect cell precipitates to obtain the Bacillus sp.DL-1 whole cells.
Example 4: characterization of optimal reaction conditions for preparing (R) -1-phenethyl alcohol by using (+/-) styrofol acetate through whole-cell resolution
(1) Evaluation standard and determination method of reaction effect: the enantiomeric excess (e.e) of the product 1-phenylethyl alcohol produced by the reaction.p) The larger the substrate conversion (C) is, the closer to 50%, the better the reaction effect is. If the two can not be satisfied simultaneously, the e.e is preferably selected.pGreater reaction conditions. The reaction product was extracted from the aqueous phase by ethyl acetate and then detected by a gas chromatography chiral column, and the e.e was calculated from the peak area.pAnd C.
Equation 1:equation 2:
Rnoland SnolRespectively shows the peak areas of (R) -1-phenethyl alcohol and (S) -1-phenethyl alcohol. R0And S0Respectively representing the concentration of the substrate of the corresponding configuration before reaction; r and S represent the substrate concentrations of the corresponding configuration after the reaction, respectively.
(2) Reaction conditions are as follows: the optimal reaction conditions for preparing (R) -1-phenethyl alcohol by the complete cell resolution of (+/-) -styrofol acetate by Bacillus sp.DL-1 are as follows: the reaction system comprises a Bacillus sp.DL-1 whole cell with the cell concentration of 48mg/mL (WCW), 50mM substrate (+/-) -styrofol acetate, 5% (v/v) methanol and the balance of PB buffer solution with the pH value of 6.0, the reaction temperature is 40 ℃, and the reaction time is 0.5 h. The gas chromatogram before and after the reaction for preparing the (R) -1-phenethyl alcohol with high optical purity by the selective hydrolysis of the (+/-) styrofoam acetate by the bacillus DL-1 whole cells under the optimal conditions is shown in figure 2 and figure 3. The enantiomeric excess (e.e) of the (R) -1-phenylethyl alcohol prepared under the above-mentioned optimum reaction conditions.p) Is 96.6 percentThe conversion was 24.5% and the yield was 48.1%.
The reaction formula is shown as follows:
example 5: characterization of optimal reaction conditions for preparing (S) -styryl acetate by splitting (+/-) styryl acetate through whole cells
(1) Evaluation standard and determination method of reaction effect: enantiomeric excess (e.e) of the substrate styrofoam acetate.s) The larger the substrate conversion (C) is, the closer to 50%, the better the reaction effect is. If the two can not be satisfied simultaneously, the e.e is preferably selected.sGreater reaction conditions. The reaction product was extracted from the aqueous phase by ethyl acetate and then detected by a gas chromatography chiral column, and the e.e was calculated from the peak area.sAnd C.
Equation 3:
Sacand RacThe peak areas of (S) -styryl acetate and (R) -styryl acetate are shown, respectively.
(2) Reaction conditions are as follows: the optimal reaction conditions for preparing (S) -styryl acetate by complete cell resolution of (+/-) -styryl acetate by Bacillus sp.DL-1 are as follows: the reaction system comprises a cell concentration of 60mg/mL (WCW) bacillus Bacillus sp.DL-1, 50mM substrate (+/-) -styrofol acetate, 5% (v/v) acetone and the balance of PB buffer solution with the pH value of 6.0, and the reaction temperature is 35 ℃ and the reaction time is 5 hours. The gas chromatogram before and after the reaction for preparing the (S) -styryl acetate with high optical purity by the selective hydrolysis of (+/-) styryl acetate by the bacillus DL-1 whole cells under the optimal conditions is shown in figure 2 and figure 4. The enantiomeric excess (e.e) of the (S) -styrofoam acetate prepared under the above-described optimal reaction conditions.s) 98.4%, conversion 56.6%, yield 86.2%.
The reaction formula is shown as follows:
the above is only a preferred embodiment of the present invention, and it should be noted that the above preferred embodiment should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.
Sequence listing
<110> Nanhai ocean institute of Chinese academy of sciences
Application of <120> bacillus DL-1 whole cell in catalytic resolution of styryl acetate
<160>1
<170>SIPOSequenceListing 1.0
<210>1
<211>1434
<212>DNA
<213> Bacillus DL-1(Bacillus sp. DL-1)
<400>1
ataatctgtc acttagcggc tggctccaaa aaggttaccc caccgacttc gggtgttaca 60
aactctcgtg gtgtgacggg cggtgtgtac aaggcccggg aacgtattca ccgcggcatg 120
ctgatccgcg attactagcg attccagctt catgtaggcg agttgcagcc tacaatccga 180
actgagaacg gttttatgag attagctcca cctcgcggtc ttgcagctct ttgtaccgtc 240
cattgtagca cgtgtgtagc ccaggtcata aggggcatga tgatttgacg tcatccccac 300
cttcctccgg tttgtcaccg gcagtcacct tagagtgccc aacttaatga tggcaactaa 360
gatcaagggt tgcgctcgtt gcgggactta acccaacatc tcacgacacg agctgacgac 420
aaccatgcac cacctgtcac tctgctcccg aaggagaagc cctatctcta gggttttcag 480
aggatgtcaa gacctggtaa ggttcttcgc gttgcttcga attaaaccac atgctccacc 540
gcttgtgcgg gcccccgtca attcctttga gtttcagcct tgcggccgta ctccccaggc 600
ggagtgctta atgcgttaac ttcagcacta aagggcggaa accctctaac acttagcact 660
catcgtttac ggcgtggact accagggtat ctaatcctgt ttgctcccca cgctttcgcg 720
cctcagtgtc agttacagac cagaaagtcg ccttcgccac tggtgttcct ccatatctct 780
acgcatttca ccgctacaca tggaattcca ctttcctctt ctgcactcaa gtctcccagt 840
ttccaatgac cctccacggt tgagccgtgg gctttcacat cagacttaag aaaccacctg 900
cgcgcgcttt acgcccaata attccggata acgcttgcca cctacgtatt accgcggctg 960
ctggcacgta gttagccgtg gctttctggt taggtaccgt caaggtgcca gcttattcaa 1020
ctagcacttg ttcttcccta acaacagagt tttacgaccc gaaagccttc atcactcacg 1080
cggcgttgct ccgtcagact ttcgtccatt gcggaagatt ccctactgct gcctcccgta 1140
ggagtctggg ccgtgtctca gtcccagtgt ggccgatcac cctctcaggt cggctacgca 1200
tcgttgcctt ggtgagccgt tacctcacca actagctaat gcgacgcggg tccatccata 1260
agtgacagcc gaagccgcct ttcaatttcg aaccatgcgg ttcaaaatgt tatccggtat 1320
tagccccggt ttcccggagt tatcccagtc ttatgggcag gttacccacg tgttactcac 1380
ccgtccgccg ctaacttcat aagagcaagc tcttaatcca ttcgctcgac tgca 1434
Claims (6)
1. The application of the whole cell of the Bacillus sp.DL-1 in catalyzing the asymmetric hydrolysis of (+/-) -styrofoam acetate, wherein the Bacillus sp.DL-1 has a preservation number of: GDMCC 1.1696.
2. The use according to claim 1, wherein the use of the whole cells of Bacillus sp.dl-1 for the catalytic resolution of (±) -styroformate acetate to obtain (R) -1-phenylethyl alcohol.
3. The use of claim 2, wherein the reaction system for obtaining (R) -1-phenylethyl alcohol by catalytic resolution of (±) -styryl acetate comprises: the cell concentration is 48mg/mL bacillus sp.DL-1, 50mM substrate (+/-) -styroform acetate, methanol with the volume fraction of 5%, and the balance of PB buffer solution with the pH value of 6.0, wherein the cell concentration is calculated by the wet weight of the cells; the reaction condition is 40 ℃ for 0.5 h.
4. The use according to claim 1, wherein said Bacillus sp.dl-1 is used for the catalytic resolution of (+ -) -styroform acetate to give (S) -styroform acetate.
5. The use of claim 4, wherein the reaction system for obtaining (S) -styryl acetate by catalytic resolution of (+ -) -styryl acetate comprises: the cell concentration is 60mg/mL Bacillus sp based on the wet weight of the cells.
DL-1, 50mM substrate (+/-) -styrofoam acetate, acetone with volume fraction of 5%, and the balance of PB buffer solution with pH 6.0; the reaction condition is 35 ℃ for 5 h.
6. A Bacillus sp.DL-1 with a preservation number of: GDMCC 1.1696.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104962533A (en) * | 2015-06-30 | 2015-10-07 | 中国科学院南海海洋研究所 | Novel esterase, encoding gene and application thereof in splitting (+/-)-1-phenethyl alcohol and (+/-)-styralyl acetate |
| CN105543190A (en) * | 2016-01-12 | 2016-05-04 | 中国科学院南海海洋研究所 | Esterase BSE00077 and encoding gene and application thereof |
| CN108285895A (en) * | 2018-01-26 | 2018-07-17 | 中国科学院南海海洋研究所 | A kind of esterase EstC11 and its encoding gene and application |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104962533A (en) * | 2015-06-30 | 2015-10-07 | 中国科学院南海海洋研究所 | Novel esterase, encoding gene and application thereof in splitting (+/-)-1-phenethyl alcohol and (+/-)-styralyl acetate |
| CN105543190A (en) * | 2016-01-12 | 2016-05-04 | 中国科学院南海海洋研究所 | Esterase BSE00077 and encoding gene and application thereof |
| CN108285895A (en) * | 2018-01-26 | 2018-07-17 | 中国科学院南海海洋研究所 | A kind of esterase EstC11 and its encoding gene and application |
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Address after: No.1119 Haibin Road, Nansha District, Guangzhou City, Guangdong Province Applicant after: SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY, CHINESE ACADEMY OF SCIENCES Address before: 510301 No. 164 West Xingang Road, Guangzhou, Guangdong, Haizhuqu District Applicant before: SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY, CHINESE ACADEMY OF SCIENCES |
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Application publication date: 20200117 |
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| RJ01 | Rejection of invention patent application after publication |