CN114150026A - Application of providencia in producing 1-substituted-propanesulfonic acid - Google Patents
Application of providencia in producing 1-substituted-propanesulfonic acid Download PDFInfo
- Publication number
- CN114150026A CN114150026A CN202110505391.2A CN202110505391A CN114150026A CN 114150026 A CN114150026 A CN 114150026A CN 202110505391 A CN202110505391 A CN 202110505391A CN 114150026 A CN114150026 A CN 114150026A
- Authority
- CN
- China
- Prior art keywords
- providencia
- propanesulfonic acid
- substituted
- use according
- application
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 241000588768 Providencia Species 0.000 title claims abstract description 33
- -1 1-substituted-propanesulfonic acid Chemical class 0.000 title claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 16
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 150000007514 bases Chemical class 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- 241000588777 Providencia rettgeri Species 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000012258 culturing Methods 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- 241000588774 Providencia sp. Species 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000009466 transformation Effects 0.000 abstract description 8
- 238000001514 detection method Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 4
- 230000036983 biotransformation Effects 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000000855 fermentation Methods 0.000 description 8
- 230000004151 fermentation Effects 0.000 description 8
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 8
- 238000009629 microbiological culture Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000003044 adaptive effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MGNVWUDMMXZUDI-UHFFFAOYSA-N propane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CCCS(O)(=O)=O MGNVWUDMMXZUDI-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P11/00—Preparation of sulfur-containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention provides an application of providencia in producing 1-substituted-propanesulfonic acid, belonging to the technical field of biosynthesis. The invention adopts providencia biotransformation to produce 1-substituted-propanesulfonic acid from organic amine and 1, 3-propane sultone, no organic reagent is used in the transformation process, the operation can be carried out under normal pressure, the reaction condition is mild, the purity of the 1-substituted-propanesulfonic acid obtained by transformation is high, the purity of the transformed product reaches 99.6 percent after purification treatment and HPLC detection, and the yield is 97 percent.
Description
Technical Field
The invention relates to the technical field of biosynthesis, in particular to application of providencia in producing 1-substituted-propanesulfonic acid.
Background
The propanesulfonic acid microbial culture agent is widely applied to the biological medicine industry and the biological vaccine culture industry, and has a larger market. At present, the propanesulfonic acid microbial culture agent is synthesized by a chemical synthesis method under the reaction condition of an organic solvent, so that by-products and impurities of the product are high, and great difficulty is brought to later purification. And the propanesulfonic acid microbial culture medium synthesized by the chemical synthesis method has a racemic structure, and needs to be chemically split into a levorotatory structure or a dextrorotatory structure when being used for microbial culture.
The propanesulfonic acid microbial culture agent synthesized by the biotransformation method has the advantages of no solvent, low reaction temperature, high yield, high product purity, easy purification and suitability for microbial culture. However, the prior art has no description and report on a propanesulfonic acid microbial culture agent synthesized by a biotransformation method.
Disclosure of Invention
The invention aims to provide the application of providencia in producing 1-substituted-propanesulfonic acid, and the method has the advantages of high yield and high product purity.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides an application of providencia in producing 1-substituted-propanesulfonic acid.
Preferably, the Providencia sp comprises Providencia rettgeri CICC 10488 from China Industrial culture Collection.
Preferably, the application comprises the following steps:
adding an organic alkaline compound and 1, 3-propane sultone in the process of culturing the providencia strain, mixing, and converting to obtain a conversion solution; the conversion solution contains 1-substituted-propanesulfonic acid.
Preferably, the organic basic compound includes a nitrogen-containing organic basic compound.
Preferably, the organic alkaline compound is selected from one or more of morpholine, monoethanolamine, diethanolamine, triethanolamine, cyclohexylamine and piperazine.
Preferably, the mass ratio of the organic basic compound to the 1, 3-propane sultone is (1: 1) to (1: 1.25).
Preferably, the inoculation amount of the providencia is 0.01-0.1 g/L; the effective viable count of the providencia is 10000-100000 cfu/g.
Preferably, the temperature of the conversion is 35-38 ℃.
The invention provides an application of providencia in producing 1-substituted-propanesulfonic acid. The invention adopts providencia to biologically convert 1, 3-propane sultone to produce 1-substituted-propane sulfonic acid, no organic reagent is used in the conversion process, the operation can be carried out under normal pressure, the reaction condition is mild, the purity of the converted 1-propane sulfonic acid is high, the purity of the converted product is up to 99.6 percent after purification treatment and HPLC detection, and the yield is 97 percent.
Detailed Description
The invention provides application of providencia in producing 1-substituted-propanesulfonic acid, and preferably application of providencia in converting 1, 3-propanesultone to produce 1-substituted-propanesulfonic acid.
In the present invention, the Providencia sp preferably includes Providencia rettgeri CICC 10488, which is purchased from china industrial microorganism culture collection management center.
In the present invention, the application preferably comprises the steps of:
adding 1, 3-propane sultone in the process of culturing the providencia strain to convert and obtain 1-propane sulfonic acid.
In the present invention, the application preferably comprises the steps of:
adding an organic alkaline compound and 1, 3-propane sultone in the process of culturing the providencia strain, mixing, and converting to obtain a conversion solution; the conversion solution contains 1-substituted-propanesulfonic acid.
In a specific embodiment of the present invention, before said transformation, said providencia is subjected to an adaptation culture comprising: adding 1, 3-propanesulfonic acid and organic alkaline substances in the process of culturing providencia to perform adaptive culture to obtain a seed solution of providencia for transformation.
In the invention, the temperature of the adaptive culture is preferably 35-40 ℃, and the time of the adaptive culture is preferably 60-72 h; in the adaptive culture process, the initial pH value of a culture system is 3.5-5.5.
In the invention, the inoculation amount of providencia is preferably 3-5 g/L, and the concentration of providencia is preferably 10000-100000 cfu/g. In the invention, the 1, 3-propanesulfonic acid is used as a carbon source, and the organic alkaline substance is used as a nitrogen source; the reagent for adjusting the pH value of the culture system is preferably a propane sulfonic acid culture medium. In the invention, the seed solution of providencia used for transformation is preserved at the temperature of 2-5 ℃.
In the invention, the organic alkaline compound is selected from one or more of morpholine, monoethanolamine, diethanolamine, triethanolamine, cyclohexylamine and piperazine.
In the present invention, the mass ratio of the organic basic compound to 1, 3-propanesultone is preferably (1: 1) to (1: 1.25).
In the invention, the inoculation amount of providencia is preferably 0.01-0.1 g/L, and more preferably 0.05 g/L; the effective viable count of the providencia is preferably 10000-100000 cfu/g.
In the invention, the temperature of the conversion is preferably 35-38 ℃.
In the present invention, the conversion process is carried out at normal pressure.
In the present invention, the conversion process does not use an organic solvent.
In the invention, the container for transformation is preferably a biological transformation container, and the volume of the biological transformation container is preferably 20-500 m3More preferably 30 to 300m3More preferably 50 to 100m3。
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Adding 14L of purified water into a 20L fermentation tank, adding 15g of 1, 3-propane sultone aqueous solution with the mass percent of 30% and 12g of morpholine aqueous solution with the mass percent of 30%, and stabilizing the temperature of the fermentation tank at 35-40 ℃. Inoculating refrigerated Providencia (Providencia rettgeri CICC 10488 from China center for culture Collection of industrial microorganisms), after 2h, starting to decrease the pH value in the fermentation tank, and respectively pumping 2900g of 1, 3-propane sultone aqueous solution with the mass percentage of 30% and 2080g of morpholine aqueous solution with the mass percentage of 30% by using a metering pump. Observing the state in the fermentation tank, and after 36h, completely pumping the raw materials. And taking out the conversion solution when the pH value of the system is stable and does not change any more.
The conversion solution is sterilized at high temperature, concentrated, crystallized and purified. The method comprises the following steps:
1) heating the product obtained by conversion, and killing providencia at high temperature.
2) Then filtered through a microporous filter with a pore size of 5 μm to obtain a liquid containing no providencia.
3) And (3) concentrating and dehydrating the liquid without providencia through a vacuum rotary evaporator under reduced pressure until a small amount of crystals appear on the inner wall, pouring out, cooling and crystallizing to obtain a crude product. Mother liquor collection for treatment the crude product was recrystallized with 0.5 weight times water. Obtaining a first product;
4) merging the mother liquor and the recrystallized mother liquor, taking out and heating to 90 ℃ when a large amount of sodium chloride crystals are obtained by vacuum concentration through a vacuum rotary evaporator, carrying out suction filtration on the mixture, wherein the solid is sodium chloride, and cooling and crystallizing the liquid to obtain a mother liquor crystallized product II;
5) the purity of the product II is more than or equal to 95 percent (HPLC) through HPLC detection; the obtained sample is detected, and the yield of the product is over 99 percent (the content of the product II is converted into 100 percent) once the product is detected by HPLC, and the purity is more than or equal to 99 percent (HPLC).
Example 2
Adding 14L of purified water into a 20L fermentation tank, adding 15g of 1, 3-propane sultone aqueous solution with the mass percent of 30% and 15g of morpholine aqueous solution with the mass percent of 30%, and stabilizing the temperature of the fermentation tank at 35-40 ℃. Inoculating refrigerated Providencia (Providencia rettgeri CICC 10488 from China center for culture Collection of industrial microorganisms), after 2h, starting to decrease the pH value in the fermentation tank, and respectively pumping 2900g of 1, 3-propane sultone aqueous solution with the mass percentage of 30% and 2080g of morpholine aqueous solution with the mass percentage of 30% by using a metering pump. Observing the state in the fermentation tank, and after 36h, completely pumping the raw materials. And taking out the conversion solution when the pH value of the system is stable and does not change any more. After the conversion solution is sterilized at high temperature, the conversion solution is concentrated, crystallized and purified according to the steps of example 1, the calculated yield of the obtained product is 97%, and the content is up to 99.6% by HPLC detection.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. Use of providencia for the production of 1-substituted-propanesulfonic acid.
2. The use according to claim 1, wherein the Providencia sp comprises Providencia rettgeri cic 10488 from the china industrial culture collection center.
3. Use according to claim 1 or 2, characterized in that it comprises the following steps:
adding an organic alkaline compound and 1, 3-propane sultone in the process of culturing the providencia strain, mixing, and converting to obtain a conversion solution; the conversion solution contains 1-substituted-propanesulfonic acid.
4. Use according to claim 3, wherein the organic basic compound comprises a nitrogen-containing organic basic compound.
5. Use according to claim 3 or 4, wherein the organic basic compound is selected from one or more of morpholine, monoethanolamine, diethanolamine, triethanolamine, cyclohexylamine and piperazine.
6. The use according to claim 5, wherein the mass ratio of the organic basic compound to 1, 3-propane sultone is (1: 1) to (1: 1.25).
7. The use according to claim 4, wherein the amount of providencia is 0.01 to 0.1 g/L; the effective viable count of the providencia is 10000-100000 cfu/g.
8. Use according to claim 3, wherein the temperature of the conversion is 35-38 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110505391.2A CN114150026B (en) | 2021-05-10 | Use of providencia in producing 1-substituted-propanesulfonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110505391.2A CN114150026B (en) | 2021-05-10 | Use of providencia in producing 1-substituted-propanesulfonic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114150026A true CN114150026A (en) | 2022-03-08 |
| CN114150026B CN114150026B (en) | 2024-05-28 |
Family
ID=
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10113198A (en) * | 1996-10-15 | 1998-05-06 | Kanegafuchi Chem Ind Co Ltd | Production of optically active 2-arylpropionic acid |
| US20070026507A1 (en) * | 2005-07-28 | 2007-02-01 | University Of Iowa Research Foundation | Microbial sulfoxidation and amidation of benzhdrylsulfanyl carboxylic acids and uses thereof |
| WO2011031744A1 (en) * | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
| CN108660167A (en) * | 2017-03-29 | 2018-10-16 | 武汉茵茂特生物技术有限公司 | The biological synthesis method of L-glufosinate-ammonium |
| WO2020090016A1 (en) * | 2018-10-30 | 2020-05-07 | Ｇｒｅｅｎ Ｅａｒｔｈ Ｉｎｓｔｉｔｕｔｅ 株式会社 | Method for producing organic compound and coryneform bacterium |
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10113198A (en) * | 1996-10-15 | 1998-05-06 | Kanegafuchi Chem Ind Co Ltd | Production of optically active 2-arylpropionic acid |
| US20070026507A1 (en) * | 2005-07-28 | 2007-02-01 | University Of Iowa Research Foundation | Microbial sulfoxidation and amidation of benzhdrylsulfanyl carboxylic acids and uses thereof |
| WO2011031744A1 (en) * | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
| CN108660167A (en) * | 2017-03-29 | 2018-10-16 | 武汉茵茂特生物技术有限公司 | The biological synthesis method of L-glufosinate-ammonium |
| WO2020090016A1 (en) * | 2018-10-30 | 2020-05-07 | Ｇｒｅｅｎ Ｅａｒｔｈ Ｉｎｓｔｉｔｕｔｅ 株式会社 | Method for producing organic compound and coryneform bacterium |
Non-Patent Citations (3)
| Title |
|---|
| HJ KWON ET AL: "Substrate specificity of a recombinant D-lyxose isomerase from Providencia stuartii for monosaccharides", 《J BIOSCI BIOENG》, vol. 111, no. 1, 31 July 2010 (2010-07-31), pages 26 - 31 * |
| ORIT REDY-KEISAR ET AL: "Synthesis and use of QCy7-derived modular probes for the detection and imaging of biologically relevant analytes", 《NATURE PROTOCOLS》, vol. 9, 5 December 2013 (2013-12-05), pages 27 - 36, XP055729142, DOI: 10.1038/nprot.2013.166 * |
| 徐航等: "普罗维登斯菌和希瓦氏菌对Pt(Ⅳ)的吸附特性", 《贵金属》, vol. 39, no. 2, 28 June 2018 (2018-06-28), pages 1 - 7 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101748161B (en) | Succinic acid purification process through anaerobic fermentation | |
| CN102533884B (en) | Method for cleanly producing glutamic acid, gamma-polyglutamic acid and organic fertilizer | |
| FI81607C (en) | Preparation of butanol by improved fermentation process | |
| CN109913512A (en) | The method of biofermentation production long-chain biatomic acid | |
| CN103804173B (en) | A kind of process for purification of fermentation organic acid | |
| CN106316869A (en) | Synthesis method of beta-alanine methyl ester salt product | |
| CN114150026A (en) | Application of providencia in producing 1-substituted-propanesulfonic acid | |
| CN114150026B (en) | Use of providencia in producing 1-substituted-propanesulfonic acid | |
| CN112047999A (en) | Preparation method of gamma-crystal form arginine perindopril salt | |
| CN103468753A (en) | Water saving method in process of producing sodium gluconate through aspergillus niger fermentation | |
| CN108456698B (en) | Fermentation production method for coproducing 1, 3-propylene glycol and lactic acid based on clostridium butyricum | |
| CN103804174A (en) | Organic acid refining method | |
| CN104876817A (en) | Method for extracting succinic acid by employing succinic acid fermentation liquor | |
| CN104131061B (en) | A kind of preparation method of oxytetracycline quaternary ammonium salt | |
| CN106316870A (en) | Synthesis method of L-glycine methyl ester salt product | |
| CN112608254A (en) | Method for preparing L-citrulline | |
| CN108486173B (en) | Preparation method of alpha-ketoglutaric acid | |
| CN111961077A (en) | Preparation method of beta sodium glycerophosphate containing crystal water | |
| CN112626141B (en) | Production method of acrylamide solution | |
| CN111362280A (en) | System and method for preparing sodium thiocyanate and sodium sulfate from desulfurization waste liquid | |
| CN101104862B (en) | Method for synthesizing D-arylglycine by using heterogeneous enzyme to catalytically hydrolyzing 5-arylhydantoin | |
| CN110016485A (en) | A kind of extracting method of L-Glutamine | |
| CN113234768A (en) | Application of providencia in production of hydroxyethyl piperazine ethanesulfonic acid | |
| CN101575624A (en) | Microbial enzymes racemization preparation method of DL-alanine | |
| CN114540433B (en) | Technological method for producing succinic acid and purification method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant |