CA1216846A - Purification of trehalose dimycolates and product - Google Patents
Purification of trehalose dimycolates and productInfo
- Publication number
- CA1216846A CA1216846A CA000426844A CA426844A CA1216846A CA 1216846 A CA1216846 A CA 1216846A CA 000426844 A CA000426844 A CA 000426844A CA 426844 A CA426844 A CA 426844A CA 1216846 A CA1216846 A CA 1216846A
- Authority
- CA
- Canada
- Prior art keywords
- fact
- tdm
- process according
- trehalose dimycolates
- solvent
- 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.)
- Expired
Links
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 title claims abstract description 9
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 title claims abstract description 9
- 238000000746 purification Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000741 silica gel Substances 0.000 claims abstract description 7
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 7
- 239000002245 particle Substances 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 241000187481 Mycobacterium phlei Species 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 241000186227 Corynebacterium diphtheriae Species 0.000 claims description 3
- 241000186367 Mycobacterium avium Species 0.000 claims description 3
- 241000186363 Mycobacterium kansasii Species 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 3
- -1 ligroin Chemical compound 0.000 claims description 3
- 201000008827 tuberculosis Diseases 0.000 claims description 3
- 241000187480 Mycobacterium smegmatis Species 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 241000589343 Methylobacter luteus Species 0.000 claims 1
- 208000036366 Sensation of pressure Diseases 0.000 claims 1
- 229960005335 propanol Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- 108010039939 Cell Wall Skeleton Proteins 0.000 description 11
- 210000004520 cell wall skeleton Anatomy 0.000 description 11
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 9
- 210000002421 cell wall Anatomy 0.000 description 8
- 239000012535 impurity Substances 0.000 description 5
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000186366 Mycobacterium bovis Species 0.000 description 2
- 241001467552 Mycobacterium bovis BCG Species 0.000 description 2
- 241000187563 Rhodococcus ruber Species 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 description 1
- 229920000189 Arabinogalactan Polymers 0.000 description 1
- 239000001904 Arabinogalactan Substances 0.000 description 1
- 241000589567 Brucella abortus Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000237074 Centris Species 0.000 description 1
- 108090000317 Chymotrypsin Proteins 0.000 description 1
- 241001445332 Coxiella <snail> Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 235000019312 arabinogalactan Nutrition 0.000 description 1
- 229960000190 bacillus calmette–guérin vaccine Drugs 0.000 description 1
- 229960002376 chymotrypsin Drugs 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C12P19/12—Disaccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37284382A | 1982-04-29 | 1982-04-29 | |
| US372,843 | 1982-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1216846A true CA1216846A (en) | 1987-01-20 |
Family
ID=23469848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000426844A Expired CA1216846A (en) | 1982-04-29 | 1983-04-27 | Purification of trehalose dimycolates and product |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS58219122A (enrdf_load_stackoverflow) |
| AU (1) | AU565095B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1216846A (enrdf_load_stackoverflow) |
| DE (1) | DE3315264A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2526027B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2119794B (enrdf_load_stackoverflow) |
| IT (1) | IT1164201B (enrdf_load_stackoverflow) |
| NZ (1) | NZ204021A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63200162U (enrdf_load_stackoverflow) * | 1987-06-05 | 1988-12-23 | ||
| KR101858770B1 (ko) * | 2010-07-02 | 2018-05-16 | 인터벳 인터내셔널 비.브이. | 에를리키아 카니스에 대한 백신 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2001118A1 (enrdf_load_stackoverflow) * | 1968-02-01 | 1969-09-26 | Kyowa Hakko Kogyo Kk | |
| FR2160326B1 (enrdf_load_stackoverflow) * | 1971-11-19 | 1975-02-07 | Anvar | |
| JPS5129292A (ja) * | 1974-09-02 | 1976-03-12 | Kyowa Hakko Kogyo Kk | Hatsukohonyorugurukoosu oyobi toreharoosu no shibosanesuteru no seizoho |
| FR2319373A1 (fr) * | 1975-07-29 | 1977-02-25 | Anvar | Nouveau procede d'esterification selective des fonctions alcool primaire de diholosides et produits ainsi obtenus |
| US4307229A (en) * | 1979-11-07 | 1981-12-22 | Avraham Liav | 6,6'-Diesters of trehalose and process for the synthesis thereof |
-
1983
- 1983-04-27 DE DE19833315264 patent/DE3315264A1/de active Granted
- 1983-04-27 NZ NZ204021A patent/NZ204021A/en unknown
- 1983-04-27 CA CA000426844A patent/CA1216846A/en not_active Expired
- 1983-04-28 AU AU14016/83A patent/AU565095B2/en not_active Ceased
- 1983-04-28 JP JP58074182A patent/JPS58219122A/ja active Granted
- 1983-04-28 IT IT20835/83A patent/IT1164201B/it active
- 1983-04-28 GB GB08311593A patent/GB2119794B/en not_active Expired
- 1983-04-28 FR FR8307012A patent/FR2526027B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2119794B (en) | 1986-04-03 |
| FR2526027B1 (fr) | 1987-03-27 |
| FR2526027A1 (fr) | 1983-11-04 |
| JPS58219122A (ja) | 1983-12-20 |
| GB8311593D0 (en) | 1983-06-02 |
| GB2119794A (en) | 1983-11-23 |
| JPS6257166B2 (enrdf_load_stackoverflow) | 1987-11-30 |
| AU565095B2 (en) | 1987-09-03 |
| DE3315264C2 (enrdf_load_stackoverflow) | 1988-02-25 |
| IT1164201B (it) | 1987-04-08 |
| DE3315264A1 (de) | 1983-12-01 |
| IT8320835A0 (it) | 1983-04-28 |
| NZ204021A (en) | 1986-11-12 |
| IT8320835A1 (it) | 1984-10-28 |
| AU1401683A (en) | 1983-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |