WO2001058860A1 - Tensio-actifs du type 1-o-l-arginyl ester 3-o-monoacyl glycerides et 1-o-l-arginyl ester 2,3-o-diacyl glycerides - Google Patents
Tensio-actifs du type 1-o-l-arginyl ester 3-o-monoacyl glycerides et 1-o-l-arginyl ester 2,3-o-diacyl glycerides Download PDFInfo
- Publication number
- WO2001058860A1 WO2001058860A1 PCT/ES2001/000039 ES0100039W WO0158860A1 WO 2001058860 A1 WO2001058860 A1 WO 2001058860A1 ES 0100039 W ES0100039 W ES 0100039W WO 0158860 A1 WO0158860 A1 WO 0158860A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- arginyl
- prot
- glycerol
- ester
- arginine
- Prior art date
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 18
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 8
- 239000004475 Arginine Substances 0.000 claims abstract description 22
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 8
- 230000000694 effects Effects 0.000 claims abstract description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 30
- 235000009697 arginine Nutrition 0.000 claims description 21
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 108090000790 Enzymes Proteins 0.000 claims description 11
- 102000004190 Enzymes Human genes 0.000 claims description 11
- -1 tert-butyloxycarbonyl (Boc) groups Chemical group 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 230000002255 enzymatic effect Effects 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 108090001060 Lipase Proteins 0.000 claims description 5
- 102000004882 Lipase Human genes 0.000 claims description 5
- 239000004367 Lipase Substances 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 235000019421 lipase Nutrition 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 239000004365 Protease Substances 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 2
- 229930064664 L-arginine Natural products 0.000 claims description 2
- 235000014852 L-arginine Nutrition 0.000 claims description 2
- 102000035195 Peptidases Human genes 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000001311 chemical methods and process Methods 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 108010048733 Lipozyme Proteins 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000011942 biocatalyst Substances 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000003093 cationic surfactant Substances 0.000 claims 1
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 6
- 230000000845 anti-microbial effect Effects 0.000 abstract description 5
- 239000007787 solid Substances 0.000 abstract description 4
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 230000008025 crystallization Effects 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract description 2
- 238000004255 ion exchange chromatography Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000004366 reverse phase liquid chromatography Methods 0.000 abstract description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 14
- 235000001014 amino acid Nutrition 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000010647 peptide synthesis reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000013456 study Methods 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- SNEIUMQYRCDYCH-UHFFFAOYSA-N acetylarginine Chemical compound CC(=O)NC(C(O)=O)CCCN=C(N)N SNEIUMQYRCDYCH-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001483 arginine derivatives Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 150000002313 glycerolipids Chemical class 0.000 description 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- SJSSFUMSAFMFNM-NSHDSACASA-N (2s)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 SJSSFUMSAFMFNM-NSHDSACASA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- RSYYQCDERUOEFI-UHFFFAOYSA-N 2-benzamido-5-(diaminomethylideneazaniumyl)pentanoate Chemical compound NC(N)=NCCCC(C(O)=O)NC(=O)C1=CC=CC=C1 RSYYQCDERUOEFI-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000193755 Bacillus cereus Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 102000053002 Lipase-like Human genes 0.000 description 1
- 108700039553 Lipase-like Proteins 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- SNEIUMQYRCDYCH-LURJTMIESA-N N(alpha)-acetyl-L-arginine Chemical compound CC(=O)N[C@H](C(O)=O)CCCNC(N)=N SNEIUMQYRCDYCH-LURJTMIESA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 108090000526 Papain Proteins 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000007068 beta-elimination reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
Definitions
- Ri can be a hydrogen or an acetyl group (Ac).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Sheet Holders (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
La présente invention concerne de nouveaux composés tensio-actifs dérivés de l'arginine du type mono et diacylglycéride, représentés par la formule générale (I) et conçus pour agir en tant qu'agents de surface à activité antimicrobienne. Les variations d'activité varieront en fonction du nombre de chaînes grasses et de leur longueur. La purification des produits intermédiaires et finaux s'obtient par extractions liquide-liquide, liquide-solide, par cristallisations, et par chromatographie par échange d'ions et en phase inverse (CLHP).
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2001231769A AU2001231769A1 (en) | 2000-02-11 | 2001-02-08 | 1-o-l-arginyl ester 3-o-monoacyl glycerides and 1-o-l-arginyl ester 2,3-o-diacylglycerides type surface active agents |
| US10/214,402 US7015019B2 (en) | 2000-02-11 | 2002-08-07 | 1-O-L-arginyl ester 3-O-monoacyl glycerides and 1-O-L-arginyl ester 2,3-O-diacyl glycerides type surface active agents |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200000319U ES1046117Y (es) | 2000-02-11 | 2000-02-11 | Muelle doble efecto |
| ESP200000319 | 2000-02-11 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/214,402 Continuation US7015019B2 (en) | 2000-02-11 | 2002-08-07 | 1-O-L-arginyl ester 3-O-monoacyl glycerides and 1-O-L-arginyl ester 2,3-O-diacyl glycerides type surface active agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2001058860A1 true WO2001058860A1 (fr) | 2001-08-16 |
Family
ID=8492265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/ES2001/000039 WO2001058860A1 (fr) | 2000-02-11 | 2001-02-08 | Tensio-actifs du type 1-o-l-arginyl ester 3-o-monoacyl glycerides et 1-o-l-arginyl ester 2,3-o-diacyl glycerides |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES1046117Y (fr) |
| WO (1) | WO2001058860A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006056636A1 (fr) * | 2004-11-19 | 2006-06-01 | Consejo Superior De Investigaciones Científicas | Composes du type n-n-acyloxypropyle lysine methyle ester et n,n-bis(n-acyloxypropyl)lysine methyle ester et leur application comme tensioactifs a activite antimicrobienne |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8303312A1 (es) * | 1982-05-28 | 1983-02-16 | Consejo Superior Investigacion | "nuevo procedimiento para la preparacion de acidos n-acil-l-alquilaminoguanidinicos y cualquiera de sus sales, como agentes tensioactivos de accion antimicrobiana". |
| EP0320976A1 (fr) * | 1987-12-18 | 1989-06-21 | Ajinomoto Co., Inc. | Dérivés d'arginine et compositions cosmétiques les contenant |
| WO1996021642A1 (fr) * | 1995-01-10 | 1996-07-18 | Laboratorios Miret, S.A. | Procede de synthese de tensioactifs cationiques derives de la condensation d'acides gras avec des aminoacides dibasiques esterifies, et leur application en tant qu'agents antimicrobiens |
| ES2130980A1 (es) * | 1997-03-10 | 1999-07-01 | Consejo Superior Investigacion | Procedimiento enzimatico para la preparacion de lipoaminoacidos del tipo alquil amidas y esteres. |
-
2000
- 2000-02-11 ES ES200000319U patent/ES1046117Y/es not_active Expired - Fee Related
-
2001
- 2001-02-08 WO PCT/ES2001/000039 patent/WO2001058860A1/fr active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8303312A1 (es) * | 1982-05-28 | 1983-02-16 | Consejo Superior Investigacion | "nuevo procedimiento para la preparacion de acidos n-acil-l-alquilaminoguanidinicos y cualquiera de sus sales, como agentes tensioactivos de accion antimicrobiana". |
| EP0320976A1 (fr) * | 1987-12-18 | 1989-06-21 | Ajinomoto Co., Inc. | Dérivés d'arginine et compositions cosmétiques les contenant |
| WO1996021642A1 (fr) * | 1995-01-10 | 1996-07-18 | Laboratorios Miret, S.A. | Procede de synthese de tensioactifs cationiques derives de la condensation d'acides gras avec des aminoacides dibasiques esterifies, et leur application en tant qu'agents antimicrobiens |
| ES2130980A1 (es) * | 1997-03-10 | 1999-07-01 | Consejo Superior Investigacion | Procedimiento enzimatico para la preparacion de lipoaminoacidos del tipo alquil amidas y esteres. |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE CAPLUS [online] R. YOSHIDA ET AL.: "Surfactants derived from aminoacids. Some surface-active properties and antimicrobial activity of the salts of long-chain N-alpha-acyl-L-arginine esters", accession no. STN Database accession no. 1976:510386 * |
| YUKAGAKU, vol. 25, 1976, pages 404 - 408 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006056636A1 (fr) * | 2004-11-19 | 2006-06-01 | Consejo Superior De Investigaciones Científicas | Composes du type n-n-acyloxypropyle lysine methyle ester et n,n-bis(n-acyloxypropyl)lysine methyle ester et leur application comme tensioactifs a activite antimicrobienne |
| ES2265245A1 (es) * | 2004-11-19 | 2007-02-01 | Consejo Superior Investig. Cientificas | Compuestos del tipo nepsilon-n-aciloxipropil lisina metil ester y nepsilon,nepsilon'-bis(n-aciloxipropil) lisina metil ester y su aplicacion. |
| ES2265245B1 (es) * | 2004-11-19 | 2008-02-01 | Consejo Superior Investig. Cientificas | Compuestos del tipo nepsilon-n-aciloxipropil lisina metil ester y nepsilon,nepsilon'-bis(n-aciloxipropil) lisina metil ester y su aplicacion. |
Also Published As
| Publication number | Publication date |
|---|---|
| ES1046117U (es) | 2000-11-16 |
| ES1046117Y (es) | 2001-05-01 |
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