DE2907190A1 - 1-desoxynojirimycin-herstellung - Google Patents
1-desoxynojirimycin-herstellungInfo
- Publication number
- DE2907190A1 DE2907190A1 DE19792907190 DE2907190A DE2907190A1 DE 2907190 A1 DE2907190 A1 DE 2907190A1 DE 19792907190 DE19792907190 DE 19792907190 DE 2907190 A DE2907190 A DE 2907190A DE 2907190 A1 DE2907190 A1 DE 2907190A1
- Authority
- DE
- Germany
- Prior art keywords
- temperature
- dsm
- deoxynojirimycin
- fermentation
- strains
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 235000015097 nutrients Nutrition 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000000855 fermentation Methods 0.000 claims abstract description 13
- 230000004151 fermentation Effects 0.000 claims abstract description 13
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 6
- 239000000600 sorbitol Substances 0.000 claims abstract description 6
- 241001112741 Bacillaceae Species 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical compound OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 claims description 26
- LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 3
- 238000005273 aeration Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 230000005526 G1 to G0 transition Effects 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 230000003698 anagen phase Effects 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000012258 culturing Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000008399 tap water Substances 0.000 description 5
- 235000020679 tap water Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 4
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 4
- 229940041514 candida albicans extract Drugs 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000012138 yeast extract Substances 0.000 description 4
- BGMYHTUCJVZIRP-UHFFFAOYSA-N Nojirimycin Natural products OCC1NC(O)C(O)C(O)C1O BGMYHTUCJVZIRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- BGMYHTUCJVZIRP-GASJEMHNSA-N nojirimycin Chemical compound OC[C@H]1NC(O)[C@H](O)[C@@H](O)[C@@H]1O BGMYHTUCJVZIRP-GASJEMHNSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 229940122816 Amylase inhibitor Drugs 0.000 description 1
- 241000193749 Bacillus coagulans Species 0.000 description 1
- 241001459867 Bacillus longisporus Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010056771 Glucosidases Proteins 0.000 description 1
- 102000004366 Glucosidases Human genes 0.000 description 1
- 241001134635 Micromonosporaceae Species 0.000 description 1
- 241000194105 Paenibacillus polymyxa Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 102000016679 alpha-Glucosidases Human genes 0.000 description 1
- 108010028144 alpha-Glucosidases Proteins 0.000 description 1
- 239000003392 amylase inhibitor Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 108010051210 beta-Fructofuranosidase Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical class CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- -1 hydrochloric acid Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000011073 invertase Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229940066779 peptones Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
- C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
- Y10S435/838—Bacillus polymyxa
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
- Y10S435/839—Bacillus subtilis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Hydrogenated Pyridines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792907190 DE2907190A1 (de) | 1979-02-23 | 1979-02-23 | 1-desoxynojirimycin-herstellung |
| US06/116,174 US4282320A (en) | 1979-02-23 | 1980-01-28 | Production of 1-desoxynojirimicin |
| AT80100552T ATE328T1 (de) | 1979-02-23 | 1980-02-04 | 1-desoxynojirimycin-herstellung. |
| EP80100552A EP0015388B1 (de) | 1979-02-23 | 1980-02-04 | 1-Desoxynojirimycin-Herstellung |
| DE8080100552T DE3060037D1 (en) | 1979-02-23 | 1980-02-04 | Preparation of 1-desoxynojirimycin |
| JP1980380A JPS55114294A (en) | 1979-02-23 | 1980-02-21 | Production of 11 desoxynodirimicine |
| ES488865A ES488865A1 (es) | 1979-02-23 | 1980-02-22 | Procedimiento para la obtencion de 1-desoxinojirimicina. |
| DK77180A DK147453C (da) | 1979-02-23 | 1980-02-22 | Fremgangsmaade til fremstilling af 1-desoxynojirimycin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792907190 DE2907190A1 (de) | 1979-02-23 | 1979-02-23 | 1-desoxynojirimycin-herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2907190A1 true DE2907190A1 (de) | 1980-08-28 |
Family
ID=6063797
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792907190 Withdrawn DE2907190A1 (de) | 1979-02-23 | 1979-02-23 | 1-desoxynojirimycin-herstellung |
| DE8080100552T Expired DE3060037D1 (en) | 1979-02-23 | 1980-02-04 | Preparation of 1-desoxynojirimycin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8080100552T Expired DE3060037D1 (en) | 1979-02-23 | 1980-02-04 | Preparation of 1-desoxynojirimycin |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4282320A (en, 2012) |
| EP (1) | EP0015388B1 (en, 2012) |
| JP (1) | JPS55114294A (en, 2012) |
| AT (1) | ATE328T1 (en, 2012) |
| DE (2) | DE2907190A1 (en, 2012) |
| DK (1) | DK147453C (en, 2012) |
| ES (1) | ES488865A1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5256788A (en) * | 1989-02-13 | 1993-10-26 | Nippon Shinyaku Co. Ltd. | Moranoline derivatives and their production and the use of moranoline and its derivatives as a stabilizing agent for enzymes |
| EP0477160B1 (en) * | 1990-09-20 | 1996-04-24 | Monsanto Company | Process for producing N-substituted-1-deoxynojirimycin |
| KR102387028B1 (ko) * | 2020-10-06 | 2022-04-14 | 이해익 | 알파-글루코시다아제 저해제를 생산하는 신규한 바실러스 코아귤란스 cc 균주 |
| CN113637605B (zh) * | 2021-08-09 | 2023-05-05 | 浙江珲达生物科技有限公司 | 一种解淀粉芽孢杆菌及其在制备1-脱氧野尻霉素中的应用 |
| CN115806913B (zh) * | 2022-10-21 | 2023-09-08 | 福建省农业科学院植物保护研究所 | 野尻链霉菌（Streptomyces nojiriensis）菌株9-13及应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3634197A (en) * | 1966-11-07 | 1972-01-11 | Sumio Umezawa | Production of 3-amino-3-deoxy-d-glucose |
| US3998698A (en) * | 1976-04-08 | 1976-12-21 | The Upjohn Company | Process for producing antibiotic U-51,640 |
| DE2658563A1 (de) * | 1976-12-23 | 1978-06-29 | Bayer Ag | Inhibitoren fuer glykosid-hydrolasen aus bacillen |
| US4307194A (en) * | 1976-12-23 | 1981-12-22 | Bayer Aktiengesellschaft | Inhibitors, obtained from bacilli, for glycoside hydrolases |
| DE2726899A1 (de) * | 1977-06-15 | 1979-04-12 | Bayer Ag | Inhibitoren fuer glykosid-hydrolasen aus bacillen |
-
1979
- 1979-02-23 DE DE19792907190 patent/DE2907190A1/de not_active Withdrawn
-
1980
- 1980-01-28 US US06/116,174 patent/US4282320A/en not_active Expired - Lifetime
- 1980-02-04 DE DE8080100552T patent/DE3060037D1/de not_active Expired
- 1980-02-04 AT AT80100552T patent/ATE328T1/de not_active IP Right Cessation
- 1980-02-04 EP EP80100552A patent/EP0015388B1/de not_active Expired
- 1980-02-21 JP JP1980380A patent/JPS55114294A/ja active Granted
- 1980-02-22 DK DK77180A patent/DK147453C/da not_active IP Right Cessation
- 1980-02-22 ES ES488865A patent/ES488865A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATE328T1 (de) | 1981-11-15 |
| JPS55114294A (en) | 1980-09-03 |
| DK147453C (da) | 1985-05-28 |
| US4282320A (en) | 1981-08-04 |
| EP0015388A1 (de) | 1980-09-17 |
| ES488865A1 (es) | 1980-09-16 |
| JPS6328599B2 (en, 2012) | 1988-06-09 |
| DK77180A (da) | 1980-08-24 |
| DE3060037D1 (en) | 1981-12-24 |
| EP0015388B1 (de) | 1981-10-21 |
| DK147453B (da) | 1984-08-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |