DE1241943B - Verfahren zur Gewinnung von Lincomycin B - Google Patents
Verfahren zur Gewinnung von Lincomycin BInfo
- Publication number
- DE1241943B DE1241943B DEU11554A DEU0011554A DE1241943B DE 1241943 B DE1241943 B DE 1241943B DE U11554 A DEU11554 A DE U11554A DE U0011554 A DEU0011554 A DE U0011554A DE 1241943 B DE1241943 B DE 1241943B
- Authority
- DE
- Germany
- Prior art keywords
- lincomycin
- water
- black
- butanol
- acid
- 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.)
- Pending
Links
- DZSDDKNXMARQMJ-AVXYAQEDSA-N (2S,4R)-4-ethyl-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1C[C@H](CC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 DZSDDKNXMARQMJ-AVXYAQEDSA-N 0.000 title claims description 33
- CWPMAVJRTHPUNS-UHFFFAOYSA-N Lincomycin B Natural products CCC1CC(NC(=O)C(C(C)O)C2OC(SC)C(O)C(O)C2O)N(C)C1 CWPMAVJRTHPUNS-UHFFFAOYSA-N 0.000 title claims description 32
- DZSDDKNXMARQMJ-UHFFFAOYSA-N N-Desmethyllincomycin Natural products CN1CC(CC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 DZSDDKNXMARQMJ-UHFFFAOYSA-N 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 13
- 239000012458 free base Substances 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 238000000855 fermentation Methods 0.000 claims description 10
- 230000004151 fermentation Effects 0.000 claims description 10
- MGUWHIXJDICIPX-NLBLSBHASA-N (2S,4R)-4-ethyl-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methylpyrrolidine-2-carboxamide hydrochloride Chemical compound Cl.CC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@@H](C)O)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O MGUWHIXJDICIPX-NLBLSBHASA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
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- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 description 15
- OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 description 14
- 229960005287 lincomycin Drugs 0.000 description 14
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
-
- 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
- C12N1/205—Bacterial isolates
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/64—Preparation of S-glycosides, e.g. lincomycin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
- C12R2001/565—Streptomyces lincolnensis
-
- 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
- Y10S435/886—Streptomyces
- Y10S435/90—Streptomyces lincolnensis
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Crystallography & Structural Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US354688A US3359164A (en) | 1964-03-25 | 1964-03-25 | Antibiotic lincomycin b and process for preparing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1241943B true DE1241943B (de) | 1967-06-08 |
Family
ID=23394495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU11554A Pending DE1241943B (de) | 1964-03-25 | 1965-03-24 | Verfahren zur Gewinnung von Lincomycin B |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3359164A (enExample) |
| AT (1) | AT266314B (enExample) |
| BE (1) | BE661627A (enExample) |
| BR (1) | BR6567744D0 (enExample) |
| CH (1) | CH468463A (enExample) |
| DE (1) | DE1241943B (enExample) |
| DK (1) | DK118712B (enExample) |
| ES (1) | ES309611A1 (enExample) |
| FI (1) | FI43578B (enExample) |
| FR (2) | FR1602611A (enExample) |
| GB (1) | GB1096841A (enExample) |
| IL (1) | IL22913A (enExample) |
| NL (1) | NL6503828A (enExample) |
| SE (1) | SE314046B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102633846A (zh) * | 2012-04-09 | 2012-08-15 | 南阳普康药业有限公司 | 一种林可霉素纯化方法 |
| CN104861007B (zh) * | 2015-06-02 | 2017-09-29 | 江苏海阔生物医药有限公司 | 一种利用树脂吸附发酵原液提取林可霉素的方法 |
| CN108801725B (zh) * | 2018-04-03 | 2020-09-08 | 新宇药业股份有限公司 | 一种盐酸林可霉素中b组分对照品的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3086912A (en) * | 1961-07-03 | 1963-04-23 | Upjohn Co | Antibiotic lincolnensin and method of production |
-
1964
- 1964-03-25 US US354688A patent/US3359164A/en not_active Expired - Lifetime
-
1965
- 1965-02-03 IL IL22913A patent/IL22913A/xx unknown
- 1965-02-19 GB GB7293/65A patent/GB1096841A/en not_active Expired
- 1965-02-20 ES ES0309611A patent/ES309611A1/es not_active Expired
- 1965-03-04 CH CH303965A patent/CH468463A/de unknown
- 1965-03-11 BR BR167744/65A patent/BR6567744D0/pt unknown
- 1965-03-15 AT AT233465A patent/AT266314B/de active
- 1965-03-22 FI FI0691/65A patent/FI43578B/fi active
- 1965-03-23 SE SE3734/65A patent/SE314046B/xx unknown
- 1965-03-24 DK DK152965AA patent/DK118712B/da unknown
- 1965-03-24 FR FR1602611D patent/FR1602611A/fr not_active Expired
- 1965-03-24 DE DEU11554A patent/DE1241943B/de active Pending
- 1965-03-25 BE BE661627D patent/BE661627A/xx unknown
- 1965-03-25 NL NL6503828A patent/NL6503828A/xx unknown
- 1965-06-23 FR FR22003A patent/FR4458M/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3086912A (en) * | 1961-07-03 | 1963-04-23 | Upjohn Co | Antibiotic lincolnensin and method of production |
Also Published As
| Publication number | Publication date |
|---|---|
| BE661627A (enExample) | 1965-09-27 |
| CH468463A (de) | 1969-02-15 |
| ES309611A1 (es) | 1965-12-16 |
| IL22913A (en) | 1969-01-29 |
| FR1602611A (en) | 1971-01-04 |
| NL6503828A (enExample) | 1965-09-27 |
| SE314046B (enExample) | 1969-09-01 |
| GB1096841A (en) | 1967-12-29 |
| FR4458M (enExample) | 1966-09-26 |
| BR6567744D0 (pt) | 1973-09-06 |
| FI43578B (enExample) | 1971-02-01 |
| AT266314B (de) | 1968-11-11 |
| US3359164A (en) | 1967-12-19 |
| DK118712B (da) | 1970-09-28 |
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