JP6436778B2 - アルコール及びその誘導体のバイオテクノロジーによる生産 - Google Patents
アルコール及びその誘導体のバイオテクノロジーによる生産 Download PDFInfo
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 239000008399 tap water Substances 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
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- AUALKMYBYGCYNY-UHFFFAOYSA-E triazanium;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+) Chemical compound [NH4+].[NH4+].[NH4+].[Fe+3].[Fe+3].[Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O AUALKMYBYGCYNY-UHFFFAOYSA-E 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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Images
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Description
α=cphase1/cphase2
(式中、c1及びc2は、それぞれ、第1及び第2の相における化合物のモル平衡濃度であり、定数kは温度依存性の分配係数である)。二相系が水相とオクタノールを含む相を含む場合、化合物の分布特性はKow又はP値を用いて記載されてもよい:
Kow=P=cOctanol/cWater
ラウリン酸メチルエステルの、ω−ヒドロキシラウリン酸を経由するω−アミノラウリン酸(ALS)メチルエステルへの転換を、菌株W3110ΔFadE[alkB−alaD−TA]及びW3110[alkB−alaD−TA]を用いて、DASGIPからの8つの容器を備える並列発酵システムで行った。
生体内変換が進行すると、酸素と炭素の移動速度は、W3110[alkB−alaD−TA]の場合に大幅に増加する。これとは対照的に、酸素と炭素の移動速度は、欠失変異体W3110ΔFadE[alkB−alaD−TA]の場合には減少し、生体内変換の前に観察されるレベルに近づく(図3)。両方の菌株によって形成された生成物の量は同等であり(図4)、実際に、収率は変異体を用いた場合よりもわずかに良好である。
Claims (19)
- 野生型と比較して低下した脂肪酸分解能を有し且つ組換えアルカンオキシダーゼを発現する微生物であって、ここで、前記微生物が大腸菌であり、前記脂肪酸分解能は、脂肪酸インポーター、脂肪酸CoAリガーゼ、アシルCoAデヒドロゲナーゼ、2,4−ジエノイル−CoAレダクターゼ、エノイル−CoAヒドラターゼ及び3−ケトアシル−CoAチオラーゼからなる群から選択されるβ−酸化経路に関与する酵素をコードする遺伝子の欠失によって、それぞれの野生型における同等の条件下で同一の酵素の活性に対して少なくとも40%活性が低下されており、前記組み換えアルカンオキシダーゼが、ルブレドキシン依存性アルカンオキシダーゼ、チトクロームP450酵素、キシレンモノオキシゲナーゼ及びメタンモノオキシゲナーゼからなる群から選択される、ことを特徴とする、前記微生物。
- 組み換えアルカンオキシダーゼが、シュードモナスプチダからのAlkGである、請求項1に記載の微生物。
- 微生物が、更に組換えアルコールデヒドロゲナーゼを発現する、請求項1または2に記載の微生物。
- 微生物が、更に組換えトランスアミナーゼを発現する、請求項1から3までのいずれか1項に記載の微生物。
- 微生物が、更に組換えアミノ酸デヒドロゲナーゼを発現する、請求項1から4までのいずれか1項に記載の微生物。
- 組換えアミノ酸デヒドロゲナーゼが、アラニンデヒドロゲナーゼである、請求項5に記載の微生物。
- a)アルキルと、野生型と比較して低下した脂肪酸分解能を有し且つ組換えアルカンオキシダーゼを発現する微生物を含む水溶液とを接触させ、ここで、前記微生物が大腸菌であり、前記脂肪酸分解能は、β−酸化経路に関与する酵素をコードする遺伝子の欠失、阻害または不活性化によって低下されており、前記微生物中で発現したアルカンオキシダーゼが、ルブレドキシン依存性アルカンオキシダーゼ、チトクロームP450酵素、キシレンモノオキシゲナーゼ及びメタンモノオキシゲナーゼからなる群から選択され;かつ、
b)工程a)からの水溶液と水非混和性有機溶媒とを接触させることを含む、アルキルの酸化方法であって、ここで、アルキルが、式H−(CH2)x−R(式中、xは少なくとも6であり、且つRは−OH、−COH、−COOH、−COOR1、−NH2、−NO2、−CN、−OPO3H、−SO3H及び−Hからなる群から選択されるものであり、ここでR1は非置換の直鎖状アルキルである)によって表される化合物であることを特徴とする、前記方法。 - 請求項7に記載の方法であって、アルキル酸化を完了させた後に、工程b)を実施する、前記方法。
- 請求項7または8に記載の方法であって、アルキル酸化を完了させ、かつ水溶液から細胞を除去した後に、工程b)を実施する、前記方法。
- 請求項7に記載の方法であって、工程b)を工程a)と同時に実施する、前記方法。
- アルキルが直鎖状アルカンである、請求項7から10までのいずれか1項に記載の方法。
- 水非混和性有機溶媒が水非混和性脂肪酸又は脂肪酸エステルである、請求項7から11までのいずれか1項に記載の方法。
- β−酸化経路に関与する酵素が、脂肪酸インポーター、脂肪酸CoAリガーゼ、アシルCoAデヒドロゲナーゼ、2,4−ジエノイル−CoAレダクターゼ、エノイル−CoAヒドラターゼ及び3−ケトアシル−CoAチオラーゼからなる群から選択される、請求項7から12までのいずれか1項に記載の方法。
- 微生物が、更に組換えアルコールデヒドロゲナーゼを発現する、請求項7から13までのいずれか1項に記載の方法。
- 微生物が、更に組換えトランスアミナーゼを発現する、請求項7から14までのいずれか1項に記載の方法。
- 微生物が、更に組換えアミノ酸デヒドロゲナーゼを発現する、請求項7から15までのいずれか1項に記載の方法。
- 組換えアミノ酸デヒドロゲナーゼが、アラニンデヒドロゲナーゼである、請求項16に記載の方法。
- 野生型と比較して低下した脂肪酸分解能を有し且つ組換えアルカンオキシダーゼを発現する微生物をアルキルの酸化に用いる使用であって、ここで、前記微生物が大腸菌であり、前記脂肪酸分解能が、β−酸化経路に関与する酵素をコードする遺伝子の欠失、阻害または不活性化によって低下されており、前記微生物中で発現したアルカンオキシダーゼが、ルブレドキシン依存性アルカンオキシダーゼ、チトクロームP450酵素、キシレンモノオキシゲナーゼ及びメタンモノオキシゲナーゼからなる群から選択されていることを特徴とする、前記使用。
- アルキルが直鎖状アルカンである、請求項18に記載の使用。
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EP11195222.2A EP2607479A1 (en) | 2011-12-22 | 2011-12-22 | Biotechnological production of alcohols and derivatives thereof |
EPEP11195222.2 | 2011-12-22 | ||
PCT/EP2012/075587 WO2013092426A1 (en) | 2011-12-22 | 2012-12-14 | Biotechnological production of alcohols and derivatives thereof |
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EP2631298A1 (en) | 2012-02-22 | 2013-08-28 | Evonik Industries AG | Biotechnological method for producing butanol and butyric acid |
EP2647696A1 (de) | 2012-04-02 | 2013-10-09 | Evonik Degussa GmbH | Verfahren zur aeroben Herstellung von Alanin oder einer unter Verbrauch von Alanin entstehenden Verbindung |
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EP2700448A1 (de) | 2012-08-21 | 2014-02-26 | Evonik Industries AG | Verzweigte Fettsäuren als flüssige Kationenaustauscher |
EP2746397A1 (de) | 2012-12-21 | 2014-06-25 | Evonik Industries AG | Herstellung von Omega-Aminofettsäuren |
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US20050176121A1 (en) | 2001-09-06 | 2005-08-11 | Ryo Takeshita | Method for producing alcohol by using microorganism |
RU2294370C2 (ru) * | 2001-09-06 | 2007-02-27 | Адзиномото Ко., Инк. | Способ получения спирта с использованием микроорганизма |
EP1350788A3 (de) | 2002-03-28 | 2003-11-12 | Degussa AG | Verfahren zur Herstellung von Hexamethylendiamin aus Butadien |
EP1350761A1 (de) | 2002-03-28 | 2003-10-08 | Degussa AG | Verfahren zur Herstellung von Wasserstoffperoxid |
DE50213288D1 (de) | 2002-05-31 | 2009-04-02 | Evonik Degussa Gmbh | Geträgerter Rutheniumkatalysator und Verfahren zur Hydrierung eines aromatischen Amins in Gegenwart dieses Katalysators |
DE10231119A1 (de) | 2002-07-10 | 2004-02-05 | Degussa Ag | Verfahren zur Selektivitätserhöhung der Hydrierung von 4,4'-Diaminodiphenylmethan zu 4,4'-Diaminodicyclohexylmethan in Gegenwart eines N-Alkyl-4,4'-Diaminodiphenylmethans |
DE10247495A1 (de) | 2002-10-11 | 2004-04-22 | Degussa Ag | Verfahren zur Epoxidierung cyclischer Alkene |
EP1424332A1 (en) | 2002-11-26 | 2004-06-02 | Degussa AG | Process for the purification of crude propene oxide |
US6878836B2 (en) | 2003-06-18 | 2005-04-12 | Degussa Ag | Process for the epoxidation of propene |
EP1828088B1 (de) | 2004-12-20 | 2008-02-27 | Evonik Degussa GmbH | Verfahren zur rückgewinnung von methanol |
DE102006017760A1 (de) | 2006-03-24 | 2007-09-27 | Ufz-Umweltforschungszentrum Leipzig-Halle Gmbh | Verfahren zur enzymatischen Herstellung von 2-Hydroxy-2-methylcarbonsäuren |
WO2007131720A1 (en) | 2006-05-11 | 2007-11-22 | Cosmoferm B.V. | Improved production of sphingoid bases using genetically engineered microbial strains |
DE102006025821A1 (de) | 2006-06-02 | 2007-12-06 | Degussa Gmbh | Ein Enzym zur Herstellung von Mehylmalonatsemialdehyd oder Malonatsemialdehyd |
DE102007021199B4 (de) | 2006-07-17 | 2016-02-11 | Evonik Degussa Gmbh | Zusammensetzungen aus organischem Polymer als Matrix und anorganischen Partikeln als Füllstoff, Verfahren zu deren Herstellung sowie deren Verwendung und damit hergestellte Formkörper |
DE102007005072A1 (de) | 2007-02-01 | 2008-08-07 | Evonik Degussa Gmbh | Verfahren zur fermentativen Herstellung von Cadaverin |
DE102007015583A1 (de) | 2007-03-29 | 2008-10-02 | Albert-Ludwigs-Universität Freiburg | Ein Enzym zur Herstellung von Methylmalonyl-Coenzym A oder Ethylmalonyl-Coenzym A sowie dessen Verwendung |
DE102007027006A1 (de) | 2007-06-08 | 2008-12-11 | Evonik Degussa Gmbh | Mikrobiologische Herstellung von Aldehyden, insbesondere von 3-Hydroxypropionaldehyd |
DE102007031689A1 (de) | 2007-07-06 | 2009-01-08 | Evonik Goldschmidt Gmbh | Enzympräparate |
DE102007035646A1 (de) | 2007-07-27 | 2009-01-29 | Evonik Goldschmidt Gmbh | Über SIC- und über Carbonsäureestergruppen verknüpfte lineare Polydimethylsiloxan-Polyoxyalkylen-Blockcopolymere, ein Verfahren zur ihrer Herstellung und ihre Verwendung |
DE102007052463A1 (de) | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Fermentative Gewinnung von Aceton aus erneuerbaren Rohstoffen mittels neuen Stoffwechselweges |
DE102007060705A1 (de) * | 2007-12-17 | 2009-06-18 | Evonik Degussa Gmbh | ω-Aminocarbonsäuren oder ihre Lactame, herstellende, rekombinante Zellen |
DE102008004725A1 (de) | 2008-01-16 | 2009-07-23 | Evonik Goldschmidt Gmbh | Verfahren zur heterogenkatalysierten Herstellung von Carbonsäurederivaten |
DE102008004726A1 (de) | 2008-01-16 | 2009-07-23 | Evonik Goldschmidt Gmbh | Verfahren zur enzymatischen Herstellung von Carbonsäureestern |
DE102008000266A1 (de) | 2008-02-11 | 2009-08-13 | Evonik Goldschmidt Gmbh | Die Erfindung betrifft die Verwendung von Schaumstabilisatoren, die auf Basis nachwachsender Rohstoffe hergestellt werden, zur Herstellung von Polyurethanschäumen |
US8048654B2 (en) * | 2010-06-09 | 2011-11-01 | Joule Unlimited Technologies, Inc. | Methods and compositions for the recombinant biosynthesis of fatty acids and esters |
JP2011167071A (ja) * | 2008-05-22 | 2011-09-01 | Ajinomoto Co Inc | L−アミノ酸の製造法 |
DE102008002090A1 (de) | 2008-05-30 | 2009-12-03 | Evonik Degussa Gmbh | Ungesättigte Dicarbonsäuren aus ungesättigten cyclischen Kohlenwasserstoffen und Acrylsäure mittels Metathese, deren Verwendung als Monomere für Polyamide, Polyester, Polyurethane sowie weitere Umsetzung zu DIolen und Diaminen |
DE102008002715A1 (de) | 2008-06-27 | 2009-12-31 | Evonik Röhm Gmbh | 2-Hydroxyisobuttersäure produzierende rekombinante Zelle |
DE102008040193A1 (de) | 2008-07-04 | 2010-01-07 | Evonik Röhm Gmbh | Verfahren zur Herstellung freier Carbonsäuren |
DE102008040415A1 (de) | 2008-07-15 | 2010-01-21 | Evonik Röhm Gmbh | Thermisches Salzspalten von Ammoniumcarboxylaten |
WO2010022090A1 (en) | 2008-08-18 | 2010-02-25 | Ls9, Inc. | Systems and methods for the production of mixed fatty esters |
DE102008041754A1 (de) | 2008-09-02 | 2010-03-04 | Evonik Goldschmidt Gmbh | Enzympräparate |
MY194500A (en) * | 2008-10-28 | 2022-11-30 | Genomatica Inc | Methods and Compositions for Producing Fatty Alcohols |
DE102009000592A1 (de) | 2009-02-04 | 2010-08-05 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Aminogruppen tragenden, multizyklischen Ringsystemen |
DE102009000662A1 (de) | 2009-02-06 | 2010-08-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Aldehyden und Ketonen aus primären und sekundären Alkoholen |
DE102009000661A1 (de) | 2009-02-06 | 2010-08-12 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 2,6-Dioxabicyclo-(3.3.0)-octan-4,8-dion[1S,5S] |
DE102009009580A1 (de) | 2009-02-19 | 2010-08-26 | Evonik Degussa Gmbh | Verfahren zur Herstellung freier Säuren aus ihren Salzen |
DE102009015211A1 (de) | 2009-03-31 | 2010-10-14 | Evonik Goldschmidt Gmbh | Selbstvernetzende Polysiloxane in Beschichtungen von Enzymimmobilisaten |
DE102009002371A1 (de) | 2009-04-15 | 2010-10-21 | Evonik Goldschmidt Gmbh | Verfahren zur Herstellung von geruchlosen Polyetheralkoholen mittels DMC-Katalysatoren und deren Verwendung in kosmetischen und/oder dermatologischen Zubereitungen |
DE102009002811A1 (de) | 2009-05-05 | 2010-11-11 | Evonik Degussa Gmbh | Enzymatisches Verfahren zur Herstellung von Aldehyden |
DE102009029651A1 (de) | 2009-09-22 | 2011-03-24 | Evonik Röhm Gmbh | Verfahren zur Herstellung freier Carbonsäuren |
CA2774975C (en) * | 2009-09-25 | 2019-11-05 | Ls9, Inc. | Production of fatty acid derivatives in recombinant bacterial cells expressing an ester synthase variant |
DE102009046626A1 (de) | 2009-11-11 | 2011-05-12 | Evonik Degussa Gmbh | Candida tropicalis Zellen und deren Verwendung |
DE102009046623A1 (de) | 2009-11-11 | 2011-05-12 | Evonik Röhm Gmbh | Verwendung eines zu einem MeaB-Protein homologen Proteins zur Erhöhung der enzymatischen Aktivität einer 3-Hydroxycarbonsäure-CoA-Mutase |
DE102010014680A1 (de) | 2009-11-18 | 2011-08-18 | Evonik Degussa GmbH, 45128 | Zellen, Nukleinsäuren, Enzyme und deren Verwendung sowie Verfahren zur Herstellung von Sophorolipiden |
DE102009046910A1 (de) | 2009-11-20 | 2011-05-26 | Evonik Degussa Gmbh | Verfahren zur Aufarbeitung eines Laurinlactam enthaltenen Stoffstroms für die Rückgewinnung aller enthaltene Wertstoffkomponenten durch Kombination von Kristallisation mit nachgeschalteter Destillation |
US20120315366A1 (en) | 2009-12-23 | 2012-12-13 | Evonik Degussa Gmbh | Sweetener and method of production thereof |
DE102010002809A1 (de) | 2010-03-12 | 2011-11-17 | Evonik Degussa Gmbh | Verfahren zur Herstellung von linearen alpha,omega-Dicarbonsäurediestern |
DE102010015807A1 (de) | 2010-04-20 | 2011-10-20 | Evonik Degussa Gmbh | Biokatalytisches Oxidationsverfahren mit alkL-Genprodukt |
DE102010026196A1 (de) | 2010-06-25 | 2011-12-29 | Evonik Degussa Gmbh | Synthese von omega-Aminocarbonsäuren und deren Estern aus ungesättigten Fettsäurederivaten |
DE102010032484A1 (de) | 2010-07-28 | 2012-02-02 | Evonik Goldschmidt Gmbh | Zellen und Verfahren zur Herstellung von Rhamnolipiden |
DE102011004465A1 (de) | 2010-09-10 | 2012-03-15 | Evonik Degussa Gmbh | Verfahren zur direkten Aminierung sekundärer Alkohole mit Ammoniak zu primären Aminen |
DE102011075162A1 (de) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Verfahren zur homogen-katalysierte, hochselektiven direkten Aminierung von primären Alkoholen mit Ammoniak zu primären Aminen bei hohem Volumenverhältnis von Flüssig- zu Gasphase und/oder hohen Drücken |
UA112980C2 (uk) | 2011-02-16 | 2016-11-25 | Евонік Дегусса Гмбх | Рідкі катіоніти |
WO2012113475A1 (de) | 2011-02-21 | 2012-08-30 | Evonik Degussa Gmbh | Verfahren zur direkten aminierung von alkoholen mit ammoniak zu primären aminen mittels eines xantphos katalysatorsystems |
DE102011015150A1 (de) | 2011-03-25 | 2012-09-27 | Evonik Degussa Gmbh | Syntese von alpha, omega-Dicarbonsäuren und deren Estern aus ungesättigten Fettsäurederivaten |
EP2697231B1 (de) | 2011-04-12 | 2015-02-18 | Evonik Degussa GmbH | Kontinuierlich betreibbares verfahren zur herstellung von carbonylverbindungen mittels eines nitroxylradikalhaltigen katalysators |
EP2557176A1 (en) | 2011-06-15 | 2013-02-13 | Evonik Degussa GmbH | Enzymatic amination |
DE102011110946A1 (de) | 2011-08-15 | 2016-01-21 | Evonik Degussa Gmbh | Biotechnologisches Syntheseverfahren von omegafunktionalisierten Carbonsäuren und Carbonsäure-Estern aus einfachen Kohlenstoffquellen |
DE102011110945A1 (de) | 2011-08-15 | 2013-02-21 | Evonik Degussa Gmbh | Biotechnologisches Syntheseverfahren von organischen Verbindungen mit alkIL-Genprodukt |
DE102011110959A1 (de) | 2011-08-18 | 2013-02-21 | Evonik Degussa Gmbh | Pichia ciferrii Zellen und deren Verwendung |
DE102011084518A1 (de) | 2011-10-14 | 2013-04-18 | Evonik Industries Ag | Verwendung einer Mehrschichtfolie mit Polyamid- und Polyesterschichten fürdie Herstellung photovoltaischer Module |
EP2602329A1 (de) | 2011-12-05 | 2013-06-12 | Evonik Degussa GmbH | Biotechnologische Herstellung von 3-Hydroxyisobuttersäure |
EP2602328A1 (de) | 2011-12-05 | 2013-06-12 | Evonik Industries AG | Verfahren zur Oxidation von Alkanen unter Verwendung einer AlkB Alkan 1-Monooxygenase |
EP2607490A1 (de) | 2011-12-22 | 2013-06-26 | Evonik Industries AG | Verfahren zur verbesserten Abtrennung einer hydrophoben organischen Lösung von einem wässrigen Kulturmedium |
EP2631298A1 (en) | 2012-02-22 | 2013-08-28 | Evonik Industries AG | Biotechnological method for producing butanol and butyric acid |
EP2639308A1 (de) | 2012-03-12 | 2013-09-18 | Evonik Industries AG | Enzymatische omega-Oxidation und -Aminierung von Fettsäuren |
EP2653538A1 (de) | 2012-04-20 | 2013-10-23 | Evonik Industries AG | NADP-abhängige Alanindehydrogenase |
US9206811B2 (en) | 2012-07-02 | 2015-12-08 | Caterpillar Inc. | Remanufactured pump and pump remanufacturing method |
EP2730655A1 (de) | 2012-11-12 | 2014-05-14 | Evonik Industries AG | Verfahren zur Umsetzung eines Carbonsäureesters unter Verwendung BioH-defizienter Zellen |
EP2746397A1 (de) | 2012-12-21 | 2014-06-25 | Evonik Industries AG | Herstellung von Omega-Aminofettsäuren |
DE102013203470A1 (de) | 2013-03-01 | 2014-09-04 | Evonik Industries Ag | Verfahren zur Herstellung von Ketonen aus Epoxiden |
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- 2012-12-14 US US14/367,610 patent/US20150275245A1/en not_active Abandoned
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- 2012-12-14 JP JP2014547874A patent/JP6436778B2/ja active Active
- 2012-12-14 CN CN201280063376.6A patent/CN103998597A/zh active Pending
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US11421254B2 (en) | 2022-08-23 |
EP2607479A1 (en) | 2013-06-26 |
DK2794850T3 (da) | 2019-08-12 |
WO2013092426A1 (en) | 2013-06-27 |
BR112014015155A2 (pt) | 2017-06-13 |
US20210024967A1 (en) | 2021-01-28 |
JP2015502163A (ja) | 2015-01-22 |
BR112014015155A8 (pt) | 2017-06-13 |
CN103998597A (zh) | 2014-08-20 |
EP2794850A1 (en) | 2014-10-29 |
US20150275245A1 (en) | 2015-10-01 |
CN109797127A (zh) | 2019-05-24 |
EP2794850B1 (en) | 2019-05-22 |
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