DK2403953T3 - Fremgangsmåde til stereoselektiv enzymatisk reduktion af ketoforbindelser - Google Patents
Fremgangsmåde til stereoselektiv enzymatisk reduktion af ketoforbindelser Download PDFInfo
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- DK2403953T3 DK2403953T3 DK10706255.6T DK10706255T DK2403953T3 DK 2403953 T3 DK2403953 T3 DK 2403953T3 DK 10706255 T DK10706255 T DK 10706255T DK 2403953 T3 DK2403953 T3 DK 2403953T3
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- Prior art keywords
- ala
- gly
- val
- leu
- alkyl
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- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
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- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/06—Ethanol, i.e. non-beverage
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/16—Butanols
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
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- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
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- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Biotechnology (AREA)
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- General Chemical & Material Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (10)
1. Fremgangsmåde til stereoselektiv, især enantioselektiv enzymatisk reduktion af ketoforbindelser til de tilsvarende chirale hydroxyforbindelser, hvor ketoforbindelserne reduceres med en bakteriel enantioselektiv, NADH-speci-fik oxidoreduktase, kendetegnet ved, at der til brug for reduktionen af ketoforbindelserne anvendes et polypeptid, som har en R-ADH-signatur H-[P; A]-[I; A; Q; V; L]-[G; K]-R ved position 205-209 og har følgende yderligere strukturelle træk i deres helhed: (i) en N-terminal Rossmann-Fold GxxxGxG, (ii) et NAG-Motiv ved position 87, (iii) en katalytisk triade, bestående af S 139, Y 152 og K 156, (iv) en negativt ladet aminosyrerest ved position 37, (v) to C-terminale motiver i dimeriseringsdomænet [A; S]-S-F og [V; l]-DG-[G; A]-Y-[T; C; L]-[A; T; S]-[Q; V; R; L; P], (vi) Val eller Leu ved position 159, (vii) Asn ved position 178, og (viii) en prolinrest ved position 188, hvor positionen af de strukturelle træk er bestemt af Multi-way aminosyre-sammenligning med Scoring-Matrix BLOSUM 62 med referencesekvensen 2bhd_Strex med aminosyresekvensen: MHDLTGKNV1ITGGARGL GAEAARQAVMGAHVLIT DVL DD DGENAARELG DRARFL HH D VTSEEDWSRAADFAVTEFGALHGLVNNAGISTGTPLESESVDHFRKVLDVNLTGVFIGMK TVVPALKEAGGGSIVNISSAAGLMGLALTAGYGASKWGVRGLTKIGAVEWGTARVRVNSV HPGMTYTPMTAAVGIERGEGKYPNTPMGRVGEADEIAGAVVFLLS DAASYVTGAELAVDG GW'i'TGPTVAYVMGQ og aminosyresekvenserne SEQ ID NO:1 til SEQ ID NO:7.
2. Fremgangsmåde ifølge krav 1, kendetegnet ved, at der til brug for reduktionen af ketoforbindelserne anvendes en funktionel oxidoreduktase, (a) som haren af aminosyresekvenserne SEQ ID NO:1 til SEQ ID NO:7 eller (b) ved hvilken mindst 70 % af aminosyrerne er identiske med aminosyrerne afen af aminosyresekvenserne SEQ ID NO:1 bis SEQ ID NO:7 eller (c) for hvilken en nukleinsyresekvens fra gruppen bestående af SEQ ID NO:8 til SEQ ID NO:14 koder eller (d) for hvilken en nukleinsyresekvens koder, som hybridiserer med en af nu-kleinsyresekvenserne nævnt i (c) under stringente betingelser.
3. Fremgangsmåde ifølge krav 1 eller 2, kendetegnet ved, at ketoforbindel-serne med den almene formel I anvendes,
(i) i hvilken R-ι, R2 og R3 er uafhængigt udvalgt fra gruppen bestående af 1) -H, under den forudsætning, at Ri ikke er H, 2) -(CrC2o)-alkyl, hvor alkyl er ligekædet eller forgrenet, 3) -(C2-C20)-alkenyl, hvor alkenyl er ligekædet eller forgrenet og eventuelt indeholder op til fire dobbeltbindinger, 4) -(C2-C 20)-alkinyl, hvor alkinyl er ligekædet eller forgrenet og eventuelt indeholder op til fire tredobbeltbindinger, 5) -(C6-C24)-aryl, 6) -(Ci-C8)-alkyl-(C6-Ci4)-aryl, 7) -(C5-Ci4)-heterocyklus, 8) -(C3-C7)-cycloalkyl, hvor resterne nævnt ovenfor under 2) til 8) er usubstitueret eller uafhængigt af hinanden er substitueret en, to eller tre gange med -OH, halogen, -N02, -NH2, -NHP og/eller -M, hvor P betegner -(CrC7)-alkyl, -(C2-C7)-alkenyl, -(C2-C7)-alkinyl, -(C6-Ci4)-aryl eller en beskyttelsesgruppe, udvalgt blandt ben-zyloxycarbonyl, triphenylmethyl og t-butylcarbonyl, og M betegner -(Ci-C7)-alkyl, -(C2-C7)-alkenyl, -(C2-C7)-alkinyl, -(C6-Ci4)-aryl, eller -(CrC8)-alkyl-(C6-Ci4)-aryl, hvor -(C6-Ci4)-aryl i -(CrC8)-alkyl-(C6-Ci4)-aryl er usubstitueret eller er substitueret en, to eller tre gange med halogen, og
4. Fremgangsmåde ifølge krav 1 eller 2, kendetegnet ved, at der som keto-forbindelser anvendes diketoner med den almene formel II
(Π) i hvilken R5 betegner (CH2)n, hvor n = 0-20, -(C6-Ci4)-aryl eller -(C5-Ci4)-heterocyklus, R4 og R6 uafhængigt af hinanden betegner -(CrC20)-alkyl eller en estergruppe, hvor R4, R5 og R6 er usubstitueret eller uafhængigt af hinanden er substitueret en, to eller tre gange med -(CrC4)-alkyl, -OH, halogen, -N02 og/eller -NH2.
5. Fremgangsmåde ifølge et af kravene 1 til 4, kendetegnet ved, at - den oxiderede cofaktor NAD, der dannes ved oxidoreduktasen/dehydroge-nasen, regenereres kontinuerligt, og - der med henblik på cofaktorregenereringen anvendes en sekundær alkohol med den almene formel RxRYCHOH, hvor Rx og RY uafhængigt af hinanden er en forgrenet eller ikke forgrenet CrC8-alkylgruppe og Ciait ^ 3.
6. Fremgangsmåde ifølge krav 5, kendetegnet ved, at der som hhv. cosub-strat og sekundær alkohol anvendes en alkohol fra gruppen bestående af 2-propanol, 2-butanol, 2-pentanol, 4-methyl-2-pentanol, 2-heptanol og 2-octa-nol, fortrinsvis 2-propanol.
7. Fremgangsmåde ifølge et af kravene 1 til 6, kendetegnet ved, at ketofor-bindelsen anvendes i en mængde på 3 % til 50 %, foretrukket på 5 % til 40 %, især på 10 % - 30 %, i forhold til det samlede volumen.
8. Fremgangsmåde ifølge et af kravene 1 til 7, kendetegnet ved, at TTN (total turn over number = mol ketoforbindelse/ mol anvendt cofactor) er >103.
9. Fremgangsmåde ifølge et af kravene 1 til 8, kendetegnet ved, at den udføres i et vandigt organisk tofasesystem.
9) -CH2-X-R, hvor X betegner O eller S og R er udvalgt blandt -(CrC7)-alkyl, phenyl og benzyl, hvor phenyl og benzyl er substitueret en, to eller tre gange med -(Ci-C7)-alkyl, -S(Ci-C3)-alkyl, -0(CrC3)-alkyl, -N02, -SCF3, halogen, -C(0)(Ci-C3)-alkyl og/eller -CN, eller Ri sammen med R2, Ri sammen med R3 eller R2 sammen med R3 danner en ring med 3-6 C-atomer, som er usubstitueret eller uafhængigt af hinanden er substitueret en, to eller tre gange med -OH, halogen, - NO2, -NH2, -NHP og/eller -M, og den øvrige rest er udvalgt blandt resterne nævnt ovenfor under 1) til 9).
10. Fremgangsmåde ifølge et af kravene 1 til 9, kendetegnet ved, at der derudover anvendes et organisk opløsningsmiddel, udvalgt blandt diethyl-ether, tertiær-butylmethylether, diisopropylether, dibutylether, ethylacetat, bu-tylacetat, heptan, hexan og cyclohexan.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09450050A EP2226386A1 (de) | 2009-03-05 | 2009-03-05 | Verfahren zur stereoselektiven enzymatischen Reduktion von Ketoverbindungen |
| PCT/EP2010/052701 WO2010100195A1 (de) | 2009-03-05 | 2010-03-03 | Verfahren zur stereoselektiven enzymatischen reduktion von ketoverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2403953T3 true DK2403953T3 (da) | 2017-07-24 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10706255.6T DK2403953T3 (da) | 2009-03-05 | 2010-03-03 | Fremgangsmåde til stereoselektiv enzymatisk reduktion af ketoforbindelser |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9045780B2 (da) |
| EP (2) | EP2226386A1 (da) |
| JP (1) | JP5852885B2 (da) |
| KR (1) | KR101780510B1 (da) |
| CN (1) | CN102341501B (da) |
| CA (1) | CA2753634C (da) |
| DK (1) | DK2403953T3 (da) |
| ES (1) | ES2636473T3 (da) |
| HU (1) | HUE033100T2 (da) |
| IL (1) | IL214972A (da) |
| PL (1) | PL2403953T3 (da) |
| PT (1) | PT2403953T (da) |
| SI (1) | SI2403953T1 (da) |
| TW (1) | TWI589696B (da) |
| WO (1) | WO2010100195A1 (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103276027A (zh) * | 2013-05-10 | 2013-09-04 | 苏州汉酶生物技术有限公司 | 一种手性n-保护哌啶醇的生物制备方法 |
| CN106754775B (zh) * | 2016-12-23 | 2019-08-20 | 华东理工大学 | 一种羰基还原酶突变体及其基因与应用 |
| CN109576313B (zh) * | 2017-09-29 | 2022-02-22 | 尚科生物医药（上海）有限公司 | 一种制备（s）- 2-氯-1-（3-羟基苯基）乙醇的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014573C1 (da) | 1990-05-07 | 1991-10-10 | Forschungszentrum Juelich Gmbh, 5170 Juelich, De | |
| DK0630402T3 (da) | 1992-03-13 | 1997-12-22 | Forschungszentrum Juelich Gmbh | Ny ketoesterreduktase, fremstilling deraf og anvendelse deraf til enzymatiske redoxreaktioner |
| JP3574682B2 (ja) | 1993-09-24 | 2004-10-06 | ダイセル化学工業株式会社 | 新規な酵素、該酵素を製造する方法、該酵素をコードするｄｎａ、該ｄｎａを含む形質転換体、該酵素による光学活性アルコール等の製造方法 |
| DE19610984A1 (de) | 1996-03-21 | 1997-09-25 | Boehringer Mannheim Gmbh | Alkohol-Dehydrogenase und deren Verwendung zur enzymatischen Herstellung chiraler Hydroxyverbindungen |
| CA2360376C (en) | 1999-12-03 | 2005-04-26 | Noriyuki Kizaki | Novel carbonyl reductase, gene thereof and method of using the same |
| TWI275645B (en) | 2000-02-16 | 2007-03-11 | Daicel Chemical Industries Ltd. | (R)-2-octanol dehydrogenases, methods for producing the enzymes, DNA encoding the enzymes, and methods for producing alcohols using the enzymes |
| EP1320826A2 (en) * | 2000-08-07 | 2003-06-25 | Bionetworks GmbH | Identification of short chain dehydrogenases/reductases (sdr) |
| DE10119274A1 (de) * | 2001-04-20 | 2002-10-31 | Juelich Enzyme Products Gmbh | Enzymatisches Verfahren zur enantioselektiven Reduktion von Ketoverbindungen |
| AU2003264502A1 (en) | 2002-09-19 | 2004-04-08 | Kaneka Corporation | Novel carbonyl reductase, gene thereof and method of using the same |
| JP4366097B2 (ja) | 2003-02-28 | 2009-11-18 | 住友化学株式会社 | 還元酵素遺伝子及びその利用 |
| DE10327454A1 (de) | 2003-06-18 | 2005-01-20 | Juelich Enzyme Products Gmbh | Oxidoreduktase aus Pichia capsulata |
| DE10345772A1 (de) | 2003-10-01 | 2005-04-21 | Basf Ag | Verfahren zur Herstellung von 3-Methylamino-1-(thien-2-yl)-propan-1-ol |
| EP1811021A4 (en) | 2004-10-27 | 2008-05-28 | Kaneka Corp | NEW CARBONYL REDUCTASE, GENE FOR IT AND USE THEREOF |
| AT501496B1 (de) * | 2005-02-21 | 2007-03-15 | Iep Gmbh | Verfahren zur enantioselektiven enzymatischen reduktion von ketoverbindungen |
| AT502395B1 (de) | 2005-07-27 | 2007-03-15 | Iep Gmbh | Oxidoreduktasen zur stereoselektiven reduktion von ketoverbindungen |
| DE102005044736A1 (de) | 2005-09-19 | 2007-03-22 | Basf Ag | Neue Dehydrogenasen, deren Derivate und ein Verfahren zur Herstellung von optisch aktiven Alkanolen |
| AT502185B1 (de) | 2005-09-23 | 2007-02-15 | Iep Gmbh | Verfahren zur enantioselektiven enzymatischen reduktion von ketoverbindungen |
| AT503017B1 (de) * | 2005-12-19 | 2007-07-15 | Iep Gmbh | Verfahren zur enantioselektiven enzymatischen reduktion von hydroxyketoverbindungen |
-
2009
- 2009-03-05 EP EP09450050A patent/EP2226386A1/de not_active Withdrawn
-
2010
- 2010-03-02 TW TW099105978A patent/TWI589696B/zh active
- 2010-03-03 PL PL10706255T patent/PL2403953T3/pl unknown
- 2010-03-03 KR KR1020117022944A patent/KR101780510B1/ko active IP Right Grant
- 2010-03-03 EP EP10706255.6A patent/EP2403953B1/de active Active
- 2010-03-03 WO PCT/EP2010/052701 patent/WO2010100195A1/de active Application Filing
- 2010-03-03 DK DK10706255.6T patent/DK2403953T3/da active
- 2010-03-03 HU HUE10706255A patent/HUE033100T2/en unknown
- 2010-03-03 CA CA2753634A patent/CA2753634C/en active Active
- 2010-03-03 JP JP2011552434A patent/JP5852885B2/ja active Active
- 2010-03-03 US US13/254,820 patent/US9045780B2/en active Active
- 2010-03-03 SI SI201031509T patent/SI2403953T1/sl unknown
- 2010-03-03 PT PT107062556T patent/PT2403953T/pt unknown
- 2010-03-03 CN CN201080010291.2A patent/CN102341501B/zh active Active
- 2010-03-03 ES ES10706255.6T patent/ES2636473T3/es active Active
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2011
- 2011-09-04 IL IL214972A patent/IL214972A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| PL2403953T3 (pl) | 2017-10-31 |
| IL214972A (en) | 2017-04-30 |
| EP2403953A1 (de) | 2012-01-11 |
| WO2010100195A1 (de) | 2010-09-10 |
| KR101780510B1 (ko) | 2017-09-22 |
| JP5852885B2 (ja) | 2016-02-03 |
| US9045780B2 (en) | 2015-06-02 |
| IL214972A0 (en) | 2011-11-30 |
| EP2403953B1 (de) | 2017-05-10 |
| KR20110134890A (ko) | 2011-12-15 |
| TWI589696B (zh) | 2017-07-01 |
| HUE033100T2 (en) | 2017-11-28 |
| CA2753634A1 (en) | 2010-09-10 |
| EP2226386A1 (de) | 2010-09-08 |
| TW201043696A (en) | 2010-12-16 |
| PT2403953T (pt) | 2017-08-09 |
| CA2753634C (en) | 2017-12-05 |
| SI2403953T1 (sl) | 2017-08-31 |
| JP2012519473A (ja) | 2012-08-30 |
| US20120040425A1 (en) | 2012-02-16 |
| CN102341501A (zh) | 2012-02-01 |
| CN102341501B (zh) | 2015-07-08 |
| ES2636473T3 (es) | 2017-10-05 |
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