JP6339499B2 - α−アミラーゼのスクリーニング方法 - Google Patents
α−アミラーゼのスクリーニング方法 Download PDFInfo
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- JP6339499B2 JP6339499B2 JP2014517752A JP2014517752A JP6339499B2 JP 6339499 B2 JP6339499 B2 JP 6339499B2 JP 2014517752 A JP2014517752 A JP 2014517752A JP 2014517752 A JP2014517752 A JP 2014517752A JP 6339499 B2 JP6339499 B2 JP 6339499B2
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- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
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- 229940117986 sulfobetaine Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000000341 threoninyl group Chemical class [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 102000003601 transglutaminase Human genes 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- 101150016309 trpC gene Proteins 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 101150110790 xylB gene Proteins 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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- C12N9/2405—Glucanases
- C12N9/2408—Glucanases acting on alpha -1,4-glucosidic bonds
- C12N9/2411—Amylases
- C12N9/2414—Alpha-amylase (3.2.1.1.)
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- C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
- C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
- C12Y302/01001—Alpha-amylase (3.2.1.1)
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Description
本出願は、コンピュータ読み取り可能な形態の配列表を含んでおり、これは本明細書において参照により援用される。
a)α−アミラーゼに係るデンプンなどの固体基質もしくは固定化基質に対する酵素の結合性を判定するステップ、
b)基質に対する親和性が低く、特に基質に対する結合性と活性との間の比が小さいα−アミラーゼを選択するステップ
を含む方法に関する。
a)親α−アミラーゼの表面に位置している1つまたは複数のアミノ酸における1つまたは複数のアミノ酸残基を置換し、欠失させ、または、挿入することにより変異体を生成するステップ;
b)α−アミラーゼに係るデンプンなどの固体基質もしくは固定化基質に対する結合性について変異体をテストするステップ;
c)基質に対する結合性が親α−アミラーゼよりも低い変異体を選択するステップ
を含む、親α−アミラーゼの変異体を選択する方法に関する。
α−アミラーゼ活性:「α−アミラーゼ活性」という用語は、デンプンならびに他の直鎖および分岐1,4−グリコシドオリゴ糖および多糖類の加水分解を触媒する酵素群を構成するα−1,4−グルカン−4−グルカノヒドロラーゼ(E.C.3.2.1.1)の活性を意味する。
(同等の残基×100)/(アラインメントの長さ−アラインメント中のギャップの総数)
(同等のデオキシリボヌクレオチド×100)/(アラインメントの長さ−アラインメント中のギャップの総数)
a)α−アミラーゼに係るデンプンなどの固体基質もしくは固定化基質に対する酵素の結合性を判定するステップ、
b)特に基質に対する結合性と活性との間の比が小さいα−アミラーゼといった、基質に対する結合性が低いα−アミラーゼを選択するステップ
を含む、特に低温で高い洗浄性能を有するといった、低温で高い性能を有するα−アミラーゼをスクリーニングする方法に関する。
a)親α−アミラーゼの表面に位置している1つまたは複数のアミノ酸における1つまたは複数のアミノ酸残基を置換し、欠失させ、または、挿入することにより変異体を生成するステップ;
b)α−アミラーゼに係るデンプンなどの固体基質もしくは固定化基質に対する結合性について変異体をテストするステップ;
c)基質に対する結合性が親α−アミラーゼよりも低い変異体を選択するステップ
を含む親α−アミラーゼの変異体を選択する方法に関する。
a)親α−アミラーゼの表面に位置している1つまたは複数のアミノ酸における1つまたは複数のアミノ酸残基を置換し、欠失させ、または、挿入することにより変異体を生成するステップであって、ここで、変異体は、その親α−アミラーゼに対して少なくとも90%配列同一性、好ましくは少なくとも95%配列同一性、より好ましくは少なくとも97%配列同一性、より好ましくは少なくとも98%配列同一性、および、最も好ましくは少なくとも99%配列同一性を有するステップ;
b)α−アミラーゼに係るデンプンなどの固体基質もしくは固定化基質に対する結合性について変異体をテストするステップ;ならびに
c)基質に対する結合性が親α−アミラーゼよりも低い変異体を選択するステップであって、ここで、変異体は、90%未満の結合性;好ましくは80%未満の結合性、好ましくは70%未満の結合性、好ましくは60%未満の結合性、好ましくは50%未満の結合性、好ましくは40%未満の結合性、好ましくは30%未満の結合性、より好ましくは20%未満の結合性および最も好ましくは10%未満の結合性など、親α−アミラーゼの95%未満の結合性を有するステップ。
i)変異体は、親α−アミラーゼに対して少なくとも80%、好ましくは少なくとも85%、好ましくは少なくとも87%配列同一性、好ましくは少なくとも90%、好ましくは少なくとも95%、好ましくは少なくとも97%配列同一性を有し、ならびに
ii)変異体は、親α−アミラーゼと比して、80%未満の結合性、好ましくは70%未満、好ましくは60%未満、好ましくは50%未満の結合性、好ましくは40%未満の結合性、好ましくは30%未満の結合性、より好ましくは20%未満の結合性および最も好ましくは10%未満の結合性など、低い固体基質に対する結合性を有する。
a)配列番号2におけるW140、W159、W167、Q169、W189、E194、N260、F262、W284、F289、G304、G305、R320、W347、W439、W469、G476およびG477、
b)配列番号5におけるW140、W159、W167、Q169、W189、E194、F262、W284、F289、G304、G305、K320、W347、W439、W469、G476およびG477、
c)配列番号4におけるW140、W159、W167、Q169、W189、E194、F262、W284、F289、G304、G305、K320、W347、W439、W469、G476およびG477、
d)配列番号13におけるW138、W157、W165、E167、W184、E189、E255、F257、F279、F284、G299、G300、K315、W342、R437、W467およびG475、
e)配列番号14におけるW136、W155、W163、E165、W184、E189、E255、F257、F279、F284、G299、G300、R315、W342、R437、W467およびG475、
f)配列番号15におけるW139、W158、W166、E168、W187、E192、F260、F287、G302、G303、W345、W437、W467、G474およびG475。
H183*+G184*+W140F;
H183*+G184*+Q169N;
H183*+G184*+Q169A;
H183*+G184*+W189Y+E190P;
H183*+G184*+N260D;
H183*+G184*+G477E;
H183*+G184*+G477Q;
H183*+G184*+G477K;
H183*+G184*+W189E+E190P;
H183*+G184*+A51I+W140Y;
H183*+G184*+W140Y+W189E;
H183*+G184*+W140Y+N260P;
H183*+G184*+W140Y+W284D;
H183*+G184*+W140Y+G476R;
H183*+G184*+W140Y+G477E;
H183*+G184*+W189E+W439R;
H183*+G184*+W284D+G477E;
H183*+G184*+W439R+G476R;
H183*+G184*+W439R+G477E;
H183*+G184*+E194D;
H183*+G184*+W439R+D467K;
H183*+G184*+R320M+W439R;
H183*+G184*+W439R+K485R;
H183*+G184*+Y160S;
H183*+G184*+W189F+E190P;
H183*+G184*+F262A;
H183*+G184*+Y363H;
H183*+G184*+G476E;
H183*+G184*+N260P+W439R;
H183*+G184*+N260P+G477E;
H183*+G184*+W439R+G476R;
H183*+G184*+K72S+W140Y;
H183*+G184*+G109A+M202L+Y203G;
H183*+G184*+E194S;
H183*+G184*+E345D+G477R;
H183*+G184*+K302N+W439R;
H183*+G184*+R320K+W439R;
H183*+G184*+W159Y+W167Y+F262P+W439R+W469Y+G477Q;
H183*+G184*+W159Y+W167F+N260D+W439Y+W469Y+G476K+G477Q;
H183*+G184*+W159Y+W167Y+N260D+W439R+W469V+G476E+G477K;
H183*+G184*+W159Y+W167F+N260P+F262P+W439R+W469Y+G476K+G477E;
H183*+G184*+W159Y+W167F+F262P+W439V+W469Y+G476K+G477Q;
H183*+G184*+W159Y+W167F+F262P+W469Y+G476R;
H183*+G184*+W159Y+W167Y+N260G+W439R+W469Y;
H183*+G184*+W159Y+W167Y+N260G+W439R+W469Y;
H183*+G184*+W167Y+N260D+W439R+G476Q+G477E;
H183*+G184*+W167Y+N260P+F262P+W439R+G476E+G477R;
H183*+G184*+W159Y+W167F+N260G+W439R+W469Y+G476R;
H183*+G184*+W159Y+W167Y+N260D+F262P+W439Y;
H183*+G184*+W159Y+W167F+N260P+W439Y+W469V+G476Q+G477Q;
H183*+G184*+W167Y+N260D+W439R+W469V+G476Q+G477Q;
H183*+G184*+W159Y+W167Y+N260P+F262P+W439R+G476E+G477K;
H183*+G184*+W159Y+W167F+N260P+F262P+W439Y+W469Y+G476R;
H183*+G184*+W167F+N260D+F262P+P380Q+G477K;
H183*+G184*+W167Y+N260D+F262P+W439R+W469V+G476Q+G477K;
H183*+G184*+W167Y+N260D+F262P+W439V+W469Y;
H183*+G184*+W159Y+W167Y+N260D+W439R+W469V+G476E+G477K;
H183*+G184*+W167Y+N260D+W439R+W469Y+G476E+G477K;
H183*+G184*+W159Y+W167Y+N260D+G476E+G477Q;
H183*+G184*+W159Y+W167F+N260P+F262P+W439Y+G476K+G477Q;
H183*+G184*+N260D+F262P+W469Y+G476R+G477Q;
H183*+G184*+W167Y+L230I+N260P+W469Y;
H183*+G184*+W159Y+W167Y+N260P+E439Y+G476Q+G477Q;
H183*+G184*+W167Y+F262P+W469Y+G476R+G477Q。
i)配列番号1〜12の1つに対して、少なくとも80%配列同一性、好ましくは少なくとも85%配列同一性、より好ましくは少なくとも90%配列同一性、より好ましくは少なくとも95%配列同一性、より好ましくは少なくとも97%配列同一性、より好ましくは少なくとも98%同一性を有し、
ii)90%未満の結合性;好ましくは80%未満の結合性、好ましくは70%未満の結合性、好ましくは60%未満の結合性、好ましくは40%未満の結合性、好ましくは30%未満の結合性、好ましくは20%未満の結合性および最も好ましくは10%未満の結合性など、親α−アミラーゼの95%未満の結合性である固体基質もしくは固定化基質に対する結合性を有する。
i)これらの1つに対して少なくとも80%配列同一性であって、配列番号1〜12の1つに対して好ましくは少なくとも85%配列同一性、より好ましくは少なくとも90%配列同一性、より好ましくは少なくとも95%配列同一性、より好ましくは少なくとも97%配列同一性、より好ましくは少なくとも98%同一性を有し
ii)90%未満の結合性;好ましくは80%未満の結合性、好ましくは70%未満の結合性、好ましくは60%未満の結合性、好ましくは50%未満の結合性、好ましくは40%未満の結合性、好ましくは30%未満の結合性、より好ましくは20%未満の結合性および最も好ましくは10%未満の結合性など、配列番号8を有するα−アミラーゼの95%未満の結合性である固体基質もしくは固定化基質に対する結合性を有する。
本発明の目的に関して、α−アミラーゼの固体基質もしくは固定化基質に対する結合性は、原理上は、技術分野において公知である基質に対する結合性を判定する方法のいずれかを用いて判定することが可能である。普通、このような方法は、α−アミラーゼを固体基質もしくは固定化基質と接触させ、基質に結合したα−アミラーゼの画分を判定するステップを含む。
本発明の目的のために、配列番号1、配列番号2、配列番号3、配列番号4、配列番号5、配列番号6、配列番号7、配列番号8、配列番号9、配列番号10、配列番号11、配列番号12、配列番号13、配列番号14または配列番号15において開示されている成熟型ポリペプチドが、他のα−アミラーゼにおける対応するアミノ酸残基を判定するために用いられる。他のα−アミラーゼのアミノ酸配列が配列番号1、配列番号2、配列番号3、配列番号4、配列番号5、配列番号6、配列番号7、配列番号8、配列番号9、配列番号10、配列番号11、配列番号12、配列番号13、配列番号14または配列番号15において開示されている成熟型ポリペプチドとアラインされ、このアラインメントに基づいて、配列番号2に開示されている成熟型ポリペプチドにおけるいずれかのアミノ酸残基に対応するアミノ酸位置番号が、好ましくはバージョン3.0.0以降のEMBOSSパッケージのNeedleプログラム(EMBOSS:The European Molecular Biology Open Software Suite,Rice et al.,2000,Trends Genet.16:276−277)において実装されているNeedleman−Wunschアルゴリズム(Needleman and Wunsch,1970,J.Mol.Biol.48:443−453)を用いて、判定される。
「Tyr167Gly+Arg170Gly」、「Tyr167Gly+Arg170Ala」、「Tyr167Ala+Arg170Gly」、および「Tyr167Ala+Arg170Ala」。
親α−アミラーゼはまた、配列番号1の成熟型ポリペプチドSP722に対して少なくとも80%配列同一性を有するポリペプチドであり得る。
変異体は、部位特異的突然変異誘発、合成遺伝子構築、半合成遺伝子構築、無作為突然変異誘発、シャッフリング等などの技術分野において公知であるいずれかの突然変異誘発法を用いて調製可能である。
親における必須アミノ酸は、部位特異的突然変異誘発またはアラニン走査突然変異誘発(Cunningham and Wells,1989,Science 244:1081−1085)などの技術分野において公知である手法に従って同定することが可能である。後者の技術においては、単一のアラニン突然変異が分子中のすべての残基に導入され、得られたミュータント分子が、分子の活性に重要であるアミノ酸残基を同定するためにα−アミラーゼ活性についてテストされる。また、Hilton et al.,1996,J.Biol.Chem.271:4699−4708を参照のこと。α−アミラーゼの活性部位または他の生物学的相互作用は、推定上の接触部位アミノ酸の突然変異が併用される、核磁気共嗚、結晶構造解析、電子回折または光親和性標識などの技術によって判定される、構造の物理的分析によって判定されることも可能である。例えば、de Vos et al.,1992,Science 255:306−312;Smith et al.,1992,J.Mol.Biol.224:899−904;Wlodaver et al.,1992,FEBS Lett.309:59−64を参照のこと。必須アミノ酸のアイデンティティは、親に関連するポリペプチドによるよるアイデンティティの分析から推測されることも可能である。
本発明はまた、本発明の変異体のいずれかをコードする単離されたポリヌクレオチドに関連する。
本発明はまた、制御配列に適合する条件下で好適な宿主細胞中にコード配列を発現させる1つまたは複数(いくつか)の制御配列に作動可能にリンクした本発明の変異体をコードするポリヌクレオチドを含む核酸構築物に関する。
本発明はまた、本発明のポリヌクレオチド、プロモータ、ならびに、転写および翻訳終止シグナルを含む組換え発現ベクターに関する。種々のヌクレオチドおよび制御配列が一緒になって、このような部位で変異体をコードするポリヌクレオチドの挿入または置換を可能とするために1つまたは複数(いくつか)の好都合な制限部位を含み得る組換え発現ベクターが生成される。または、ポリヌクレオチドは、ポリヌクレオチドまたはポリヌクレオチドを含む核酸構築物を発現に適切なベクターに挿入することにより発現され得る。発現ベクターの形成において、コード配列は、コード配列が、発現に適切な制御配列と作動可能にリンクするようベクター中に位置されている。
本発明はまた、本発明の変異体の生成をもたらす1つまたは複数(いくつか)の制御配列に作動可能にリンクした本発明のポリヌクレオチドを含む組換え宿主細胞に関する。ポリヌクレオチドを含む構築物もしくはベクターは、構築物もしくはベクターが染色体性組み込み体として、もしくは、既述の自己複製余剰−染色体性ベクターとして維持されるよう宿主細胞に導入される。「宿主細胞」という用語は、複製の最中に生じる突然変異により親細胞と同等ではない親細胞のいずれかの子孫を包含する。宿主細胞の選択は、変異体をコードする遺伝子およびそのソースに大きく依存することとなる。
本発明はまた:(a)本発明の宿主細胞を変異体の発現に好適な条件下で培養するステップ;および、(b)変異体を回収するステップを含む変異体を生成する方法に関する。
本発明はまた、本発明の変異体を含む組成物に関する。好ましくは、組成物は、このような変異体が富化されている。「富化」という用語は、組成物のα−アミラーゼ活性が、例えば1.1の富化因子で高められることを意味する。
一実施形態において、本発明は、本発明の酵素を1種または複数種の追加のクリーニング組成成分と共に含む洗剤組成物に関する。
本発明の一実施形態において、本発明のポリペプチドは、洗浄液1リットル当たり、0.01〜100mgのタンパク質、好ましくは0.005〜50mgのタンパク質、より好ましくは0.01〜25mgのタンパク質、さらにより好ましくは0.05〜10mgのタンパク質、最も好ましくは0.05〜5mgのタンパク質、および、さらに最も好ましくは0.01〜1mgのタンパク質などの0.001〜100mgのタンパク質に対応する量で洗剤組成物に添加され得る。
洗剤組成物は、アニオン性および/またはカチオン性および/またはノニオン性および/または半極性および/または両イオン性またはこれらの混合物であり得る1種または複数種の界面活性剤を含んでいてもよい。特定の実施形態において、洗剤組成物は、1種または複数種のノニオン性界面活性剤および1種または複数種のアニオン性界面活性剤の混合物を含む。界面活性剤は、典型的には、約1%〜約40%または約3%〜約20%または約3%〜約10%などの約0.1%〜60重量%のレベルで存在する。界面活性剤は所望のクリーニング用途に基づいて選択され、技術分野において公知であるいずれかの従来の界面活性剤を含む。ランドリー洗剤に用いられ得る技術分野において公知であるいずれかの界面活性剤が利用され得る。
ヒドロトロープは、疎水性化合物を水溶液(または、反対に、極性物質を非極性環境)中に可溶化させる化合物である。典型的には、ヒドロトロープは、親水特性および疎水特性の両方を有する(いわゆる、界面活性剤から公知である両親媒性特性)が;しかしながら、ヒドロトロープの分子構造は、一般に、自発的な自己凝集を好まず、例えば、Hodgdon and Kaler(2007),Current Opinion in Colloid & Interface Science 12:121−128による概説を参照のこと。ヒドロトロープは、ミセル相、層状相または他の良好に画定されたメソ相を形成する界面活性剤および脂質について見出されるような、超えると自己凝集を生じる限界濃度を示さない。代わりに、多くのヒドロトロープは、凝集物の大きさが濃度の増加に伴って大型化する連続タイプの凝集プロセスを示す。しかしながら、多くのヒドロトロープは、水、脂、界面活性剤およびポリマーの混合物を含む、極性および非極性特性の物質を含有する系の相挙動、安定性およびコロイド特性を改変させる。ヒドロトロープは、伝統的に、製薬、パーソナルケア、食品から技術的用途にわたり産業で用いられている。洗剤組成物中においてヒドロトロープを使用することにより、相分離または高粘度などの望ましくない現象を誘起することなく、例えば、界面活性剤のより濃縮された配合物(水を排除することにより液体洗剤をコンパクトにするプロセスのとおり)が可能となる。
洗剤組成物は、約10%〜約40%などの約0〜65重量%の洗剤ビルダーもしくはコビルダー、または、これらの混合物を含有し得る。皿洗浄洗剤において、ビルダーのレベルは、典型的には40〜65%、特に50〜65%である。ビルダーおよび/またはコビルダーは特に、CaおよびMgと共に水溶性錯体を形成するキレート化剤であり得る。ランドリーまたは皿洗浄洗剤または産業上もしくは組織的な(?)クリーニングに用いられ得る洗剤において用いられる技術分野において公知であるいずれかのビルダーおよび/またはコビルダーが利用され得る。ビルダーの非限定的な例としては、ゼオライト、二リン酸塩(ピロリン酸塩)、三リン酸ナトリウム(STPまたはSTPP)などの三リン酸塩、炭酸ナトリウムなどの炭酸塩、メタケイ酸ナトリウムなどの可溶性ケイ酸塩、層状ケイ酸塩(例えば、Hoechst製SKS−6)、2−アミノエタン−1−オール(MEA)、イミノジエタノール(DEA)および2,2’、2”−ニトリロトリエタノール(TEA)などのエタノールアミン、および、カルボキシメチルイヌリン(CMI)、ならびに、これらの組み合わせが挙げられる。
ホスホン酸塩などの湯垢抑制剤。
洗剤は、約0%〜約10%などの0〜20重量の漂白系を含有し得る。ランドリー+皿洗浄+I&I洗剤において用いられるいずれかの技術分野において公知である漂白系が利用され得る。好適な漂白系成分としては、漂白触媒、光漂白、漂白活性化剤、過炭酸ナトリウムおよび過ホウ酸ナトリウムなどの過酸化水素の供給源、事前に形成した過酸、ならびに、これらの混合物が挙げられる。好適な事前に形成した過酸としては、これらに限定されないが、ペルオキシカルボン酸および塩、過炭酸および塩、過イミド酸および塩、ペルオキシ一硫酸および塩、例えば、オキソン(R)、ならびに、これらの混合物が挙げられる。漂白系の非限定的な例としては、例えば、過ホウ酸(通常は一水和物または四水和物)、過炭酸、過硫酸、過リン酸、過ケイ酸のナトリウム塩などのアルカリ金属塩を含む無機塩を、過酸−形成性漂白活性化剤と組み合わせて含み得るペルオキシド系漂白系が挙げられる。本明細書において漂白活性化剤とは、ペルオキシド漂白剤様過酸化水素と反応して、過酸を形成する化合物を意味する。このようにして形成された過酸は、活性化された漂白剤を構成する。本明細書において用いられる好適な漂白活性化剤は、エステルアミド、イミドまたは無水物の分類に属するものを含み、好適な例は、テトラアセチルエチレンジアミン(TAED)、ナトリウム3,5,5トリメチルヘキサノイルオキシベンゼンスルホネート、ジペルオキシドデカン酸、4−(ドデカノイルオキシ)ベンゼンスルホネート(LOBS)、4−(デカノイルオキシ)ベンゼンスルホネート、4−(デカノイルオキシ)安息香酸塩(DOBS)、4−(3,5,5−トリメチルヘキサノイルオキシ)ベンゼンスルホネート(ISONOBS)、テトラアセチルエチレンジアミン(TAED)および4−(ノナノイルオキシ)ベンゼンスルホネート(NOBS)、および/または、国際公開第98/17767号パンフレットに開示されているものである。対象の漂白活性化剤の特定のファミリーは欧州特許第624154号明細書に開示されており、アセチルトリエチルシトレート(ATC)が特に好ましいファミリーである。ATCまたは短鎖トリグリセリド様トリアシンは、最終的にはクエン酸およびアルコールに分解されるために、環境にやさしいという利点を有する。さらに、アセチルトリエチルシトレートおよびトリアセチンは、保管に際して生成物中における良好な加水分解安定性を有しており、これは効果的な漂白活性化剤である。最後に、ATCは、ランドリー添加剤に対して良好な補助能を提供する。または、漂白系は、例えば、アミド、イミドまたはスルホンタイプのペルオキシドを含み得る。漂白系はまた、6−(フタロイルアミノ)過カプロン酸(PAP)などの過酸を含み得る。漂白系はまた、漂白触媒を含んでいてもよい。いくつかの実施形態において、漂白剤成分は、以下の式を有する有機触媒:
洗剤は、0.5〜5%、2〜5%、0.5〜2%または0.2〜1%などの0〜10重量%のポリマーを含有し得る。ランドリー、皿洗浄およびI&I洗剤において用いられる技術分野において公知であるいずれかのポリマーが利用され得る。ポリマーは、上記のコビルダーとして機能し得、または、再汚染防止、繊維保護、汚染物遊離、移染防止および/もしくは油脂クリーニング特性を提供し得る。例示的な再汚染防止剤ポリマーとしては、(カルボキシメチル)セルロース(CMC)、ポリ(ビニルアルコール)(PVA)、ポリ(ビニルピロリドン)(PVP)、ポリ(エチレングリコール)またはポリ(エチレンオキシド)(PEG)、エトキシル化ポリ(エチレンイミン)、ならびに、PAA、PAA/PMAおよびラウリルメタクリレート/アクリル酸コポリマーなどのポリカルボキシレートが挙げられる。例示的な繊維保護ポリマーとしては、疎水性修飾CMC(HM−CMC)およびシリコーンが挙げられる。例示的な汚染物遊離ポリマーとしては、テレフタル酸およびオリゴマー系グリコールのコポリマーが挙げられる。例示的な移染防止ポリマーとしては、PVP、ポリ(ビニルイミダゾール)(PVI)およびポリ(ビニルピリジン−N−オキシド)(PVPOまたはPVPNO)が挙げられる。他の例示的なポリマーは、例えば、国際公開第2006/130575号パンフレットに開示されている。
本発明の洗剤組成物はまた、染料または顔料などの布地色調剤を含んでいてもよく、これは、洗剤組成物に配合された場合に、前記布地が前記洗剤組成物を含む洗浄液と接触させられる際に布地に付着し、これにより、可視光の吸収/反射を介して前記布地の色合いを変えることが可能である。蛍光性白色化剤は少なくともいくらかの可視光を放つ。対照的に、布地色調剤は、可視光スペクトルの少なくとも一部分を吸収することで表面の色合いを変える。好適な布地色調剤としては、染料および染料−クレイ複合体が挙げられ、また、顔料もまた挙げられ得る。好適な染料としては、微小分子染料および高分子染料が挙げられる。好適な微小分子染料としては、例えば国際公開第2005/03274号パンフレット、国際公開第2005/03275号パンフレット、国際公開第2005/03276号パンフレットおよび欧州特許第1876226号明細書(本明細書において参照により援用される)に記載されている、Direct Blue、Direct Red、Direct Violet、Acid Blue、Acid Red、Acid Violet、Basic Blue、Basic VioletおよびBasic Red、または、これらの混合物の染料索引(C.I.)分類に属する染料からなる群から選択される微小分子染料が挙げられる。洗剤組成物は、約0.00003重量%〜約0.2重量%、約0.00008重量%〜約0.05重量%またはさらには約0.0001重量%〜約0.04重量%の布地色調剤を含むことが好ましい。組成物は、0.0001重量%〜0.2重量%の布地色調剤を含み得、これは、組成物が単位用量ポーチの形態である場合に特に好ましい場合がある。好適な色調剤はまた、例えば、国際公開第2007/087257号パンフレット、国際公開第2007/087243号パンフレットに開示されている。
洗剤添加剤、ならびに、洗剤組成物は、例えばラッカーゼおよび/またはペルオキシダーゼといった、タンパク分解酵素、リパーゼ、クチナーゼ、アミラーゼ、カルボヒドラーゼ、セルラーゼ、ペクチナーゼ、マンナナーゼ、アラビナーゼ、ガラクタナーゼ、キシラナーゼ、オキシダーゼなどの1種または複数種[追加]の酵素を含み得る。
ランドリー、皿洗浄またはI&I洗剤において用いられる技術分野において公知であるいずれかの洗剤成分もまた利用され得る。他の任意の洗剤成分としては、単独もしくは組み合わせで、耐食剤、収縮防止剤、再汚染防止剤、しわ防止剤、殺菌剤、バインダ、腐食抑制剤、崩壊剤/分解剤、染料、酵素安定化剤(ホウ酸、ホウ酸塩、CMC、および/または、プロピレングリコールなどのポリオールを含む)、クレイを含む布地コンディショナ、充填材/加工助剤、蛍光性白色化剤/光学増白剤、起泡増進剤、起泡(セッケンの泡)調節剤、香料、汚染物−懸濁剤、軟化剤、セッケン泡抑制剤、色あせ防止剤、および、ウィッキング剤が挙げられる。ランドリー、皿洗浄またはI&I洗剤において用いられる技術分野において公知であるいずれかの処方成分が利用され得る。このような処方成分の選択は十分に当業者の技能の範囲内である。
本発明の洗剤組成物は、例えば、バー、均質な錠剤、2つ以上の層を有する錠剤、通常のもしくは圧縮された粉末、顆粒、ペースト、ゲル、または、通常の圧縮もしくは濃縮液体といったいずれかの簡便な形態であり得る。
粒状洗剤は、国際公開第09/092699号パンフレット、欧州特許第1705241号明細書、欧州特許第1382668号明細書、国際公開第07/001262号パンフレット、米国特許第6472364号明細書、国際公開第04/074419号パンフレットまたは国際公開第09/102854号パンフレットに記載されているとおり配合され得る。他の有用な洗剤配合物が、国際公開第09/124162号パンフレット、国際公開第09/124163号パンフレット、国際公開第09/117340号パンフレット、国際公開第09/117341号パンフレット、国際公開第09/117342号パンフレット、国際公開第09/072069号パンフレット、国際公開第09/063355号パンフレット、国際公開第09/132870号パンフレット、国際公開第09/121757号パンフレット、国際公開第09/112296号パンフレット、国際公開第09/112298号パンフレット、国際公開第09/103822号パンフレット、国際公開第09/087033号パンフレット、国際公開第09/050026号パンフレット、国際公開第09/047125号パンフレット、国際公開第09/047126号パンフレット、国際公開第09/047127号パンフレット、国際公開第09/047128号パンフレット、国際公開第09/021784号パンフレット、国際公開第09/010375号パンフレット、国際公開第09/000605号パンフレット、国際公開第09/122125号パンフレット、国際公開第09/095645号パンフレット、国際公開第09/040544号パンフレット、国際公開第09/040545号パンフレット、国際公開第09/024780号パンフレット、国際公開第09/004295号パンフレット、国際公開第09/004294号パンフレット、国際公開第09/121725号パンフレット、国際公開第09/115391号パンフレット、国際公開第09/115392号パンフレット、国際公開第09/074398号パンフレット、国際公開第09/074403号パンフレット、国際公開第09/068501号パンフレット、国際公開第09/065770号パンフレット、国際公開第09/021813号パンフレット、国際公開第09/030632号パンフレット、および、国際公開第09/015951号パンフレット、国際公開第2011025615号パンフレット、国際公開第2011016958号パンフレット、国際公開第2011005803号パンフレット、国際公開第2011005623号パンフレット、国際公開第2011005730号パンフレット、国際公開第2011005844号パンフレット、国際公開第2011005904号パンフレット、国際公開第2011005630号パンフレット、国際公開第2011005830号パンフレット、国際公開第2011005912号パンフレット、国際公開第2011005905号パンフレット、国際公開第2011005910号パンフレット、国際公開第2011005813号パンフレット、国際公開第2010135238号パンフレット、国際公開第2010120863号パンフレット、国際公開第2010108002号パンフレット、国際公開第2010111365号パンフレット、国際公開第2010108000号パンフレット、国際公開第2010107635号パンフレット、国際公開第2010090915号パンフレット、国際公開第2010033976号パンフレット、国際公開第2010033746号パンフレット、国際公開第2010033747号パンフレット、国際公開第2010033897号パンフレット、国際公開第2010033979号パンフレット、国際公開第2010030540号パンフレット、国際公開第2010030541号パンフレット、国際公開第2010030539号パンフレット、国際公開第2010024467号パンフレット、国際公開第2010024469号パンフレット、国際公開第2010024470号パンフレット、国際公開第2010025161号パンフレット、国際公開第2010014395号パンフレット、国際公開第2010044905号パンフレット、国際公開第2010145887号パンフレット、国際公開第2010142503号パンフレット、国際公開第2010122051号パンフレット、国際公開第2010102861号パンフレット、国際公開第2010099997号パンフレット、国際公開第2010084039号パンフレット、国際公開第2010076292号パンフレット、国際公開第2010069742号パンフレット、国際公開第2010069718号パンフレット、国際公開第2010069957号パンフレット、国際公開第2010057784号パンフレット、国際公開第2010054986号パンフレット、国際公開第2010018043号パンフレット、国際公開第2010003783号パンフレット、国際公開第2010003792号パンフレット、国際公開第2011023716号パンフレット、国際公開第2010142539号パンフレット、国際公開第2010118959号パンフレット、国際公開第2010115813号パンフレット、国際公開第2010105942号パンフレット、国際公開第2010105961号パンフレット、国際公開第2010105962号パンフレット、国際公開第2010094356号パンフレット、国際公開第2010084203号パンフレット、国際公開第2010078979号パンフレット、国際公開第2010072456号パンフレット、国際公開第2010069905号パンフレット、国際公開第2010076165号パンフレット、国際公開第2010072603号パンフレット、国際公開第2010066486号パンフレット、国際公開第2010066631号パンフレット、国際公開第2010066632号パンフレット、国際公開第2010063689号パンフレット、国際公開第2010060821号パンフレット、国際公開第2010049187号パンフレット、国際公開第2010031607号パンフレット、国際公開第2010000636号パンフレットに記載されている。
本発明はまた、その組成物の使用方法に関する。
硬質面クリーニング(ADW、洗車、産業用表面)
AMSAを用いたα−アミラーゼの洗浄性能
洗剤系組成物中のα−アミラーゼ変異体の洗浄性能を評価するために、洗浄実験を実施し得る。自動機械式応力アッセイ(AMSA)を用いて酵素をテストする。AMSAテストでは、大量の小容量酵素−洗剤溶液の洗浄性能を試験可能である。AMSAプレートは、テスト溶液用の多数のスロットと、洗浄される生地布きれをすべてのスロット開口部に対してしっかりと押し込む蓋とを有する。洗浄時間の間、プレート、テスト溶液、生地および蓋を激しく振盪してテスト溶液と生地とを接触させ、規則正しい周期的な振動で機械的応力を加える。さらなる説明については、国際公開第02/42740号パンフレット、特に第23〜24頁の段落「Special method embodiments」を参照のこと。
水(15°dH)、0.8g/L洗剤(例えば以下に記載のモデル洗剤A)または50mMのHCO3-および本発明の酵素(例えば0.1、0.2、0.3、0.4、0.8および/または1.2mg酵素タンパク質/Lの濃度)を含むテスト溶液を調製する。デンプン(例えば、Center For Testmaterials BV,P.O.Box 120,3133 KT,Vlaardingen,The Netherlands製のCS−28)で汚れた布地を加え、実施例において特定されているとおり、20℃で30分間、または、15℃で20分間、または、15℃で45分間、または、15℃もしくは40℃で20分間洗浄する。水道からの流水で完全にすすぎ、暗中で乾燥させた後、洗浄性能の尺度として、汚れた布地の光強度または反射率値をその後に計測する。0mg酵素タンパク質/Lでのテストをブランクとして用いてΔレミッション値(ΔREM)を得た。または、洗浄性能は親α−アミラーゼのものと比較をし、ここでは、親α−アミラーゼの性能結果が100の値とされ、変異体の結果がこの値と比較される。洗浄ステップの最中においては、例えば布地と共に洗浄溶液を振盪、回転または攪拌するといった形態で機械的作用が適用されることが好ましい。
生地サンプルCS−28(綿上の米デンプン)は、Center For Testmaterials BV,P.O.Box 120,3133 KT Vlaardingen,the Netherlandsから入手される。
このアッセイは縦型洗濯機の小規模モデルであり、アミラーゼの洗浄性能を評価するために用いられる。
循環式水浴(5℃);ガラスビーカ(250mL);100mLの洗浄溶液容量を有するビーカ毎に1本の回転アーム;テスト布きれ:Center for Testmaterials BV,Vlaardingen,The Netherlands製のCS−28(綿上の米デンプン)およびEMPA Testmaterials AG,St.Gallen,Switzerland製のEMPA162(綿/ポリエステル上の米デンプン)であって、布きれは5×5cmに切断されている。
洗浄性能は、Δレミッション値(ΔRem)として表される。布きれの光反射率の評価を、極小の楕円形のアパーチャ、すなわち0.7cm2(約0.7×1.0cm)を有するMacbeth Color Eye 7000反射率分光測光計を用いて行った。UVを含まない入射光で計測を行い、460nmでのレミッションを抽出した。布きれを計測開口対して持ち上げるピストンからの反射を低減するために、計測の前に、計測する布きれを他の同種の布きれの上に置いた。個別の布きれに係るΔレミッション値は、アミラーゼを添加することなく洗浄した布きれのレミッション値(対照)をアミラーゼで洗浄した布きれレミッション値から減じることにより算出した。
小型洗浄ロボットは洗濯機の小規模モデルであり、アミラーゼの洗浄性能を評価するために用いられる。
α−アミラーゼ活性は、G7−pNP基質を利用する方法により判定し得る。G7−pNPは、α−アミラーゼなどのエンド−アミラーゼにより切断されることが可能であるブロックオリゴ糖(blocked oligosaccharide)である4,6−エチリデン(G7)−p−ニトロフェニル(G1)−α,D−マルトヘプタオシドに対する略記である。切断の後、キット中のα−グルコシダーゼが加水分解された基質をさらに消化して、黄色の遊離p−ニトロフェノール(pNP)分子を遊離させ、これにより、λ=405nm(400〜420nm)での可視分光法による計測が可能である。G7−pNP基質およびα−グルコシダーゼを含有するキットは、Roche/Hitachi(カタログ番号11876473)により製造されている。
このキットのG7−pNP基質は、22mMの4,6−エチリデン−G7−pNPおよび52.4mM HEPES(2−[4−(2−ヒドロキシエチル)−1−ピペラジニル]−エタンスルホン酸)、pH7.0)を含有する。
分析されるアミラーゼサンプルを希釈緩衝剤中に希釈して、確実に希釈サンプル中のpHを7とした。アッセイを、20μlの希釈酵素サンプルを96ウェルマイクロタイタープレートに移し、80μlの基質処理溶液を添加することにより行った。溶液を混合し、室温で1分プレインキュベートし、OD405nmで5分間にわたって20秒毎に吸収を計測する。
アッセイ原理:
アミラーゼ変異体は、選択されるべきα−アミラーゼの用途について意図されるpH値(例えば、洗剤用途に関して、pHは、pH8.0またはpH10.0などのアルカリ性領域内で選択されることが好適である)に応じて、pH4.0〜11.0の範囲内で選択されたpH値で;普通5分間〜1時間の間、10分または30分間などの好ましくは10〜30分の範囲内の選択された時間で;および、普通、0℃〜30℃の範囲内、好ましくは4℃での選択された温度で、不溶性の生の米デンプンの存在下もしくは不在下でインキュベートされる。遠心分離の後、アミラーゼ活性が、上澄中で判定される。米デンプンの存在下および不在下でインキュベートしたサンプルにおける活性における差異が、アミラーゼの不溶性デンプンに対する結合性の尺度である。
米デンプン(Sigma Inc,Cat No.S7260)、HEPES、塩化カルシウム、Triton X−100、グリシン、EnzChek Ultra Amylase Assay Kit(Life Technologies,カタログ番号E33651)、インキュベーションおよび希釈用96マイクロウェルプレート(Nunc、カタログ番号269620)、ならびに、蛍光計測用の半分の領域が黒色の96ウェルプレート(Corning,カタログ番号3694)。
方法の項に記載のデンプンに対する結合性の計測方法およびAMSA洗浄性能テストを用いて、多数のアミラーゼおよびその変異体をアミロースに対する結合性および洗浄性能について分析した。
原理:
原理は実施例1に記載のものと同一であるが、アミロースの代わりに、5%(w/v)米デンプン(Sigma S7260)の懸濁液のみを用いた。結合性分析を、8.0のpH、10分間の結合時間、および、4℃の温度で行った。
原理は実施例1に記載のものと同一であるが、アミロースの代わりに、コーン由来の5%(w/v)アミロペクチン(Fluka製)の懸濁液のみを用いた。
配列番号13を有するB.リケニホルミス(B.licheniformis)α−アミラーゼの変異体を形成した。テストした変異体は、配列番号13を有する親α−アミラーゼと比して、デンプンに対する結合性が低く、より良好な洗浄性能を有するものであった。
洗浄性能=値(変異体−ブランク)/値(Termamyl−ブランク)×100
配列番号2を有するα−アミラーゼの追加の変異体を生成し、変異体を基質結合性についてテストし、AMSA洗浄性能を、0.3mg酵素タンパク質/Lを用い、15℃で、モデル洗剤X中に20分間でテストした。
配列番号2を有するα−アミラーゼのさらなる変異体を生成し、変異体を基質結合性および低温での洗浄性能についてテストしたところ、選択した変異体は、修飾H183*+G184*を伴う配列番号2を有する親α−アミラーゼよりも基質結合性が低いものであった。AMSA洗浄テストを、0.3mg酵素タンパク質/Lを用い、15℃、モデル洗剤X中に20分間で行った。
配列番号2を有するα−アミラーゼのさらなる変異体を生成し、変異体を基質結合性および低温での洗浄性能についてテストしたところ、選択した変異体は、修飾H183*+G184*を伴う配列番号2を有する親α−アミラーゼよりも基質結合性が低いものであった。AMSA洗浄テストを、0.3mg酵素タンパク質/Lを用い、15℃、モデル洗剤X中に20分間で行った。
Claims (12)
- 高い洗浄性能を5〜35℃で有するα−アミラーゼをスクリーニングする方法であって、
a)デンプンに対する前記α−アミラーゼの結合性を判定するステップ;
b)前記デンプンに対する結合性が標準洗剤α−アミラーゼよりも低いα−アミラーゼを選択するステップ
を含む方法。 - 前記α−アミラーゼのデンプンに対する結合性が、配列番号8を有するα−アミラーゼの90%未満の結合性である、請求項1に記載の方法。
- a)親α−アミラーゼの表面に位置している1つまたは複数のアミノ酸における1つまたは複数のアミノ酸残基を置換し、欠失させ、または、挿入することにより変異体を生成するステップ;
b)デンプンに対する結合性について前記変異体をテストするステップ;
c)前記基質に対する結合性が前記親α−アミラーゼよりも低く、且つ、5〜35℃で高い洗浄性能を有する変異体を選択するステップ
を含む、親α−アミラーゼの変異体を選択する方法。 - 前記親α−アミラーゼが、配列番号1〜15の1つに対して、少なくとも90%配列同一性を有するアミラーゼから選択される、請求項3に記載の方法。
- 前記親α−アミラーゼが、配列番号1〜15の1つに対して、少なくとも95%配列同一性を有するアミラーゼから選択される、請求項3に記載の方法。
- 前記親α−アミラーゼが、配列番号1〜15の1つに対して、少なくとも97%配列同一性を有するアミラーゼから選択される、請求項3に記載の方法。
- 前記変異体のデンプンに対する結合性が、前記親α−アミラーゼの90%未満の結合性である、請求項3〜6のいずれか1項に記載の方法。
- α−アミラーゼ活性を有し、かつ、配列番号2に対して少なくとも90%配列同一性を有する変異体ポリペプチドであって、
配列番号2におけるアミノ酸位置を基準とした場合に、以下:
H183*+G184*+W140F;
H183*+G184*+Q169A;
H183*+G184*+W189Y+E190P;
H183*+G184*+G477E;
H183*+G184*+W140Y+G476R;
H183*+G184*+W284D+G477E;
H183*+G184*+W439R+G477E;
H183*+G184*+W439R+D467K;
H183*+G184*+R320M+W439R;
H183*+G184*+W439R+K485R;
H183*+G184*+W159Y+W167Y+N260P+F262P+W439R+G476E+G477K;および
H183*+G184*+W159Y+W167F+N260P+F262P+W439Y+G476K+G477Q;
から選択される修飾を含み、
配列番号2のアミノ酸配列からなる親α−アミラーゼと比して、デンプンに対する結合性が低く、かつ、5〜35℃での洗浄性能が高い、変異体ポリペプチド。 - 配列番号2に対して、少なくとも95%配列同一性を有する、請求項8に記載の変異体ポリペプチド。
- 配列番号2に対して、少なくとも97%配列同一性を有する、請求項8に記載の変異体ポリペプチド。
- 請求項8〜10のいずれか1項に記載の変異体α−アミラーゼを含む洗剤組成物。
- ランドリーまたは自動皿洗浄を含む硬質面クリーニングなどのクリーニングプロセスにおける請求項8〜10のいずれか1項に記載の変異体α−アミラーゼの使用。
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JP2020088875A Pending JP2020141694A (ja) | 2011-06-30 | 2020-05-21 | α−アミラーゼのスクリーニング方法 |
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ES2909509T3 (es) | 2012-06-08 | 2022-05-06 | Danisco Us Inc | Variante de alfa-amilasas con mayor actividad en polímeros de almidón |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107289172B (zh) * | 2016-03-30 | 2020-09-22 | 浙江盾安禾田金属有限公司 | 电磁阀 |
WO2022014428A1 (ja) | 2020-07-15 | 2022-01-20 | 花王株式会社 | アミラーゼ配合洗浄剤組成物 |
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MX2014000158A (es) | 2014-02-19 |
US20190352628A1 (en) | 2019-11-21 |
EP2726500A2 (en) | 2014-05-07 |
HUE058093T2 (hu) | 2022-06-28 |
BR112013033524A2 (pt) | 2017-02-07 |
EP2726500B1 (en) | 2019-03-20 |
WO2013001087A2 (en) | 2013-01-03 |
KR20140041801A (ko) | 2014-04-04 |
CN103703124B (zh) | 2021-01-15 |
JP2020141694A (ja) | 2020-09-10 |
JP2018153191A (ja) | 2018-10-04 |
MX351850B (es) | 2017-10-31 |
AU2012277729A1 (en) | 2014-01-16 |
EP3543333B1 (en) | 2022-01-05 |
JP2014520517A (ja) | 2014-08-25 |
AU2012277729B2 (en) | 2016-12-08 |
BR122020009747B1 (pt) | 2021-07-20 |
CN112662734A (zh) | 2021-04-16 |
EP4026901A2 (en) | 2022-07-13 |
IN2014CN00597A (ja) | 2015-04-03 |
US20140206026A1 (en) | 2014-07-24 |
DK3543333T3 (da) | 2022-02-14 |
EP4026901A3 (en) | 2022-11-23 |
EP3543333A3 (en) | 2019-10-23 |
EP3543333A2 (en) | 2019-09-25 |
PL3543333T3 (pl) | 2022-06-13 |
US11718840B2 (en) | 2023-08-08 |
WO2013001087A3 (en) | 2013-08-08 |
CN103703124A (zh) | 2014-04-02 |
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