CA1226545A - Tetraesters de trehalose lipidique - Google Patents

Tetraesters de trehalose lipidique

Info

Publication number: CA1226545A
Authority: CA; Canada
Prior art keywords: culture; trehalose; suspension; trowels; lipids
Prior art date: 1984-01-20
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

Application number

CA000445736A

Other languages

English (en)

Inventor

Fritz Wagner

Egbert Ristau

Zu-Yi Li

Siegmund Lang

Walther Schulz

Hans-Jurgen Hofmann

Kai-Udo Sewe

Walter Lindorfer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wintershall AG

Original Assignee

Wintershall AG

Priority date (The priority date 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 date listed.)

1984-01-20

Filing date

1984-01-20

Publication date

1987-09-08

1984-01-20 Application filed by Wintershall AG filed Critical Wintershall AG

1984-01-20 Priority to CA000445736A priority Critical patent/CA1226545A/fr

1987-09-08 Application granted granted Critical

1987-09-08 Publication of CA1226545A publication Critical patent/CA1226545A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 claims abstract description 28
244000005700 microbiome Species 0.000 claims abstract description 20
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 10
229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
150000002148 esters Chemical class 0.000 claims abstract description 8
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 abstract description 5
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 abstract description 5
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 abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 4
150000007524 organic acids Chemical class 0.000 claims abstract description 3
235000005985 organic acids Nutrition 0.000 claims abstract description 3
150000003625 trehaloses Chemical class 0.000 claims abstract 6
239000000126 substance Substances 0.000 claims abstract 3
239000000725 suspension Substances 0.000 claims description 31
230000012010 growth Effects 0.000 claims description 21
239000003350 kerosene Substances 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 9
229960001484 edetic acid Drugs 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 8
239000012266 salt solution Substances 0.000 claims description 8
235000015097 nutrients Nutrition 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 6
230000003698 anagen phase Effects 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
230000001954 sterilising effect Effects 0.000 claims description 5
238000004659 sterilization and disinfection Methods 0.000 claims description 5
229960000285 ethambutol Drugs 0.000 claims description 4
241000186216 Corynebacterium Species 0.000 claims description 3
241000316848 Rhodococcus <scale insect> Species 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229940074410 trehalose Drugs 0.000 claims 2
241000186063 Arthrobacter Species 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 claims 1
230000003385 bacteriostatic effect Effects 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
125000000129 anionic group Chemical group 0.000 abstract description 7
229910052760 oxygen Inorganic materials 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
239000001301 oxygen Substances 0.000 abstract description 3
239000003876 biosurfactant Substances 0.000 abstract 1
239000004094 surface-active agent Substances 0.000 abstract 1
150000002632 lipids Chemical class 0.000 description 47
239000000243 solution Substances 0.000 description 19
239000000203 mixture Substances 0.000 description 15
239000012188 paraffin wax Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
235000018936 Vitellaria paradoxa Nutrition 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
238000000605 extraction Methods 0.000 description 7
241000187561 Rhodococcus erythropolis Species 0.000 description 6
238000001816 cooling Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229960001866 silicon dioxide Drugs 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000009630 liquid culture Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
230000001105 regulatory effect Effects 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229930186217 Glycolipid Natural products 0.000 description 3
239000013543 active substance Substances 0.000 description 3
238000005273 aeration Methods 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000287 crude extract Substances 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229930195734 saturated hydrocarbon Natural products 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241000186359 Mycobacterium Species 0.000 description 2
241000282320 Panthera leo Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229960004132 diethyl ether Drugs 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
FGNPLIQZJCYWLE-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound OS(O)(=O)=O.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO FGNPLIQZJCYWLE-BTVCFUMJSA-N 0.000 description 1
ZTOKUMPYMPKCFX-CZNUEWPDSA-N (E)-17-[(2R,3R,4S,5S,6R)-6-(acetyloxymethyl)-3-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxyoctadec-9-enoic acid Chemical compound OC(=O)CCCCCCC/C=C/CCCCCCC(C)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(C)=O)O1 ZTOKUMPYMPKCFX-CZNUEWPDSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000007836 KH2PO4 Substances 0.000 description 1
235000006679 Mentha X verticillata Nutrition 0.000 description 1
235000002899 Mentha suaveolens Nutrition 0.000 description 1
235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
241000187654 Nocardia Species 0.000 description 1
240000007377 Petunia x hybrida Species 0.000 description 1
241001237745 Salamis Species 0.000 description 1
241000490025 Schefflera digitata Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229920000180 alkyd Chemical group 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
238000010352 biotechnological method Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
150000002016 disaccharides Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000004992 fission Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
229940073584 methylene chloride Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
235000021048 nutrient requirements Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000035699 permeability Effects 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
230000011514 reflex Effects 0.000 description 1
235000015175 salami Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

CA000445736A 1984-01-20 1984-01-20 Tetraesters de trehalose lipidique Expired CA1226545A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000445736A CA1226545A (fr)	1984-01-20	1984-01-20	Tetraesters de trehalose lipidique

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000445736A CA1226545A (fr)	1984-01-20	1984-01-20	Tetraesters de trehalose lipidique

Publications (1)

Publication Number	Publication Date
CA1226545A true CA1226545A (fr)	1987-09-08

Family

ID=4126994

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000445736A Expired CA1226545A (fr)	1984-01-20	1984-01-20	Tetraesters de trehalose lipidique

Country Status (1)

Country	Link
CA (1)	CA1226545A (fr)

1984
- 1984-01-20 CA CA000445736A patent/CA1226545A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-09-08	MKEX	Expiry

Publication	Publication Date	Title
US4720456A (en)	1988-01-19	Trehalose lipid tetraesters
SU1731067A3 (ru)	1992-04-30	Способ получени L-2-амино-4-(гидроксиметилфосфинил)-масл ной кислоты
DE4127908A1 (de)	1993-02-25	Verfahren zur induktion der rhamnolipid-produktion in pseudomonas aeruginosa staemmen mit hilfe von glycerinsaeureether-lipiden und ihre verwendung
US5093249A (en)	1992-03-03	Process for production of dihomo-γ-linolenic acid and inhibitor for unsaturation reaction at Δ5-position of fatty acid
EP1201763A3 (fr)	2002-05-08	Production de polyhydroxyalcanoates à partir d' esters d'acides gras comme matière première
CA1319636C (fr)	1993-06-29	Procede pour la production de composes de type macrolide
EP0465546A1 (fr)	1992-01-15	Production microbiologique de polyesters.
DD156986A5 (de)	1982-10-06	Verfahren zur herstellung optisch aktiver phenylpropan-derivate
EP0032830B1 (fr)	1983-03-02	Préparation d'acide 2-céto-L-gulonique
JP2009296908A (ja)	2009-12-24	マンノシルエリスリトールリピッドの製造方法
US4343814A (en)	1982-08-10	Hypocholesterolemic fermentation products
US3205150A (en)	1965-09-07	Hydroxy fatty acid production
US4355109A (en)	1982-10-19	Microbiological production of novel biosurfactants
US3909356A (en)	1975-09-30	Production of fatty acid esters of fructose
US4432996A (en)	1984-02-21	Hypocholesterolemic fermentation products and process of preparation
CZ36494A3 (en)	1994-08-17	Process for preparing predominantly one of enantiomers of optically active arylakanoic acids
DE69322720T2 (de)	1999-07-08	Verfahren zur Herstellung von Biotin
CA1140878A (fr)	1983-02-08	Preparation d'acide 2,5 - dicetogluconique
EP0570593B1 (fr)	1998-09-09	Procede de production d'un norborneol presentant une activite optique
Göbbert et al.	1988	Microbial transesterification of sugar-corynomycolates
Martín et al.	1991	Structure and bioconversion of trehalose lipids
US4461835A (en)	1984-07-24	Process for preparing optically-active isoprenoid intermediates
US4925798A (en)	1990-05-15	3-hydroxydicarboxylic acids and process for their production
US6268187B1 (en)	2001-07-31	Process for preparing lysophospholipid using enzyme
US4452897A (en)	1984-06-05	Method of preparing optically active β-(S)-aminoglutaric acid monoalkyl esters