DE3405371A1 - Verfahren zur herstellung von trehaloseestern - Google Patents
Verfahren zur herstellung von trehaloseesternInfo
- Publication number
- DE3405371A1 DE3405371A1 DE19843405371 DE3405371A DE3405371A1 DE 3405371 A1 DE3405371 A1 DE 3405371A1 DE 19843405371 DE19843405371 DE 19843405371 DE 3405371 A DE3405371 A DE 3405371A DE 3405371 A1 DE3405371 A1 DE 3405371A1
- Authority
- DE
- Germany
- Prior art keywords
- trehalose
- suspension
- ester
- separated
- cell mass
- 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
- 238000000034 method Methods 0.000 title claims abstract description 19
- 150000003625 trehaloses Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 21
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 239000011780 sodium chloride Substances 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 9
- 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 claims description 18
- 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 claims description 18
- -1 trehalose ester Chemical class 0.000 claims description 16
- 239000000725 suspension Substances 0.000 claims description 15
- 239000012188 paraffin wax Substances 0.000 claims description 14
- 244000005700 microbiome Species 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000005273 aeration Methods 0.000 claims description 4
- 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 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 235000010755 mineral Nutrition 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 6
- 235000015097 nutrients Nutrition 0.000 abstract description 6
- 239000002028 Biomass Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000006285 cell suspension Substances 0.000 description 6
- 241000187561 Rhodococcus erythropolis Species 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- LFRXCNXVZHVRSE-JEZACWOJSA-N [(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r)-3-hydroxy-2-tetradecyloctadecanoyl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]methyl (2r,3r)-3-hydroxy-2-tetradecyloctadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)[C@H](CCCCCCCCCCCCCC)[C@H](O)CCCCCCCCCCCCCCC)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(=O)[C@H](CCCCCCCCCCCCCC)[C@H](O)CCCCCCCCCCCCCCC)O1 LFRXCNXVZHVRSE-JEZACWOJSA-N 0.000 description 4
- 241000186216 Corynebacterium Species 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000284 resting effect Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000520094 Mycobacterium paraffinicum Species 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- MNBUNKPMKFIPAD-UHFFFAOYSA-N Trehalose 6-mono-corynomycolate Natural products OC1C(O)C(O)C(COC(=O)C(CCCCCCCCCCCCCC)C(O)CCCCCCCCCCCCCCC)OC1OC1C(O)C(O)C(O)C(CO)O1 MNBUNKPMKFIPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 125000003473 lipid group Chemical group 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000012138 yeast extract Substances 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
-
- 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)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843405371 DE3405371A1 (de) | 1982-12-27 | 1984-02-15 | Verfahren zur herstellung von trehaloseestern |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823248167 DE3248167A1 (de) | 1982-12-27 | 1982-12-27 | Trehaloselipidtetraester |
| DE19843405371 DE3405371A1 (de) | 1982-12-27 | 1984-02-15 | Verfahren zur herstellung von trehaloseestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3405371A1 true DE3405371A1 (de) | 1985-09-05 |
| DE3405371C2 DE3405371C2 (enrdf_load_stackoverflow) | 1987-10-08 |
Family
ID=25806922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843405371 Granted DE3405371A1 (de) | 1982-12-27 | 1984-02-15 | Verfahren zur herstellung von trehaloseestern |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3405371A1 (enrdf_load_stackoverflow) |
-
1984
- 1984-02-15 DE DE19843405371 patent/DE3405371A1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3405371C2 (enrdf_load_stackoverflow) | 1987-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AF | Is addition to no. |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8340 | Patent of addition ceased/non-payment of fee of main patent |