CN115398001A - 用于生产2,5-呋喃二甲酸的组合物和方法 - Google Patents
用于生产2,5-呋喃二甲酸的组合物和方法 Download PDFInfo
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- CN115398001A CN115398001A CN202180020764.5A CN202180020764A CN115398001A CN 115398001 A CN115398001 A CN 115398001A CN 202180020764 A CN202180020764 A CN 202180020764A CN 115398001 A CN115398001 A CN 115398001A
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
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Abstract
一种用于制备2,5‑呋喃二甲酸的化学酶方法,其包括将D‑葡萄糖与(i)选自基本上由半乳糖氧化酶、吡喃糖2‑氧化酶、葡糖二酸脱水酶、过氧化氢酶组成的组的至少两种酶及其组合接触,以产生中间体;和(ii)与非均相金属催化剂接触,以形成2,5‑呋喃二甲酸。
Description
与相关申请的交叉引用
本申请要求2020年3月12日提交的题为“用于从5-羟甲基糠醛生产2,5-呋喃二甲酸的组合物和方法”(Compositions and Methods for 2,5-Furan Dicarboxylic AcidProduction from 5-Hydroxymethylfurfural)的美国临时专利申请系列号62/988,841的利益,所述临时申请为所有目的整体通过参考并入本文。
关于联邦资助的研究或开发的陈述
不适用。
技术领域
本公开涉及高纯度2,5-呋喃二甲酸的生产。更具体来说,本公开涉及在温和条件下高纯度2,5-呋喃二甲酸的化学酶法合成。
背景技术
2,5-呋喃二甲酸(FDCA)被美国能源部视为源自于生物质的前12大增值化学品之一。FDCA被用于生产多种化合物,包括琥珀酸、呋喃-2,5-二甲酸异癸基酯、呋喃-2,5-二甲酸异壬基酯、呋喃-2,5-二甲酸二戊酯、呋喃-2,5-二甲酸二庚酯和聚(十二烷二酸乙二酯-2,5-呋喃二甲酸乙二酯)(PEDF)。FDCA是制备己酸、大环配体、杀真菌剂、腐蚀抑制剂和tiolene薄膜中的重要成分。所述化合物也可作为前体用于合成单体例如二氯、二甲基、二乙基或双(羟乙基)衍生物,用于生产聚酯、聚酰胺和增塑剂。FDCA也已在医学中用作麻醉剂、抗生素和螯合剂,用于去除肾结石。FDCA的特别有趣之处在于它是聚呋喃二甲酸乙二酯(PEF)合成的前体,所述PEF是基于石油的聚对苯二甲酸乙二酯(PET)和聚对苯二甲酸丁二酯(PEB)的替代性聚合物。PEF聚合物由用另一种可再生化学品单乙二醇(MEG)连接的呋喃-2,5-二甲酸(FDCA)单体组成。PET的单体对苯二甲酸(PTA)与FDCA之间的结构相似性允许使用现有的聚酯基础设施进行PEF聚合。此外,与PET相比,PEF表现出增强的阻隔、热和机械性能。
FDCA可以从可再生糖例如葡萄糖和果糖生产。产生FDCA的常规方法目前包括两条主要的竞争路线:1)果糖通过HMF中间体的氧化和脱水,和2)醛糖二酸的C2或C5位处的酮形成,以促进呋喃形成。
发明内容
本文公开了一种用于制备2,5-呋喃二甲酸的化学酶方法,所述方法包括:将D-葡萄糖与(i)选自基本上由半乳糖氧化酶、吡喃糖2-氧化酶、葡糖二酸脱水酶、过氧化氢酶组成的组的至少两种酶及其组合接触,以产生中间体;和(ii)将所述中间体与金属催化剂和酸催化剂接触,以形成2,5-呋喃二甲酸。
本文还公开了一种用于制备2,5-呋喃二甲酸的化学酶方法,所述方法包括:用酶氧化组合物对5-羟甲基糠醛进行酶氧化以形成中间体,所述组合物包含选自芳基醇氧化酶(AAO)、氯过氧化物酶(CPO)、5-羟甲基糠醛氧化酶(HMFO)、乙二醛氧化酶(GLOX)、周质醛氧化酶(PaoABC)、非特异性过氧化酶(UPO)、辣根过氧化物酶(HRP)、伴有或不伴有激活酶辣根过氧化物酶(HRP)的半乳糖氧化酶(GAO)、乳过氧化物酶(LPO)、髓过氧化物酶(MPO)、嗜酸性粒细胞过氧化物酶(EPO)、甲状腺过氧化物酶(TPO)、卵过氧化物酶、唾液过氧化物酶、钒卤过氧化物酶、非哺乳动物脊椎动物过氧化物酶(POX)、过氧蛋白(Pxd)、细菌过氧素(peroxicin,Pxc)、无脊椎动物过氧连接蛋白(peroxinectin,Pxt)和短过氧对接蛋白(peroxidockerin,PxDo)、短过氧对接蛋白(Pxt)、α-加双氧酶(aDox)、双重氧化酶(DuOx)、***素H合酶或环加氧酶(PGHS/CyOx)、亚油酸二醇合酶(LDS)、其功能性变体的一种或多种酶及其任何组合;和使用金属催化剂氧化所述中间体,以形成2,5-呋喃二甲酸。
附图说明
为了详细描述所公开的方法和***的各个方面,现在将参考附图,在所述附图中:
图1是来自于实施例1的样品的葡萄糖转化的比活性的图。
图2是来自于实施例2的样品的葡萄糖和葡萄糖酸盐转化的比活性的图。
图3是GAO-Mut47和GAO-Mut107对0.5和2%葡萄糖的活性的图。
图4是Parr反应中残留葡萄糖浓度的图。
图5是氧化酶类对葡萄糖和氧化衍生物的比活性的图。
图6是己二醛葡糖(Glucodialdose)或葡萄糖反应中吡喃糖2-氧化酶的HPLC-MS迹线的汇编。
图7是本文公开的类型的工艺流程图或化学酶方法的一种情况。
具体实施方式
为了更清楚地定义本文使用的术语,提供了下述定义。除非另有指明,否则下述定义适用于本公开。如果术语在本公开中使用但未在本文中具体定义,则可以应用来自于《IUPAC化学术语总目录》(IUPAC Compendium of Chemical Terminology)第二版(1997)的定义,只要该定义不与本文中任何其他公开内容或应用的定义冲突或不使应用该定义的任何权利要求项不确定或无效即可。
元素周期表中的元素族使用Chemical and Engineering News,63(5),27,1985中出版的元素周期表版本中指示的编号方案指示。在某些情况下,元素族可以使用分配给所述族的通用名来指示;例如,碱金属用于第1族元素,碱土金属用于第2族元素,过渡金属用于第3-12族元素,卤素用于第17族元素,等等。
关于权利要求项的过渡性术语或短语,与“包括”、“含有”、“具有”或“特征在于”同义的过渡性术语“包含”是包含性或开放式的,并且不排除额外的、未叙述的要素或方法步骤。过渡性短语“由……组成”排除了在权利要求项中未指定的任何要素、步骤或成分。过渡性短语“基本上由……组成”将权利要求项的范围限制到指定的材料或步骤以及那些不实质性影响要求保护的发明的基本和新颖特征的材料或步骤。短语“基本上由……组成”占据了以“由……组成”格式书写的封闭性权利要求与以“包含”格式起草的完全开放性权利要求之间的中间地带。在没有相反指示的情况下,当描述一种化合物或组合物时,“基本上由……组成”不应被解释为“包含”,而是旨在描述所叙述的组分包括不显著改变应用所述术语的组合物或方法的材料。当组合物和方法被描述为“包含”各种不同的组分或步骤时,所述组合物和方法也可以“基本上由”或“由”所述各种不同组分或步骤“组成”。
正如前面描述的,产生FDCA的常规方法目前包括两条主要的竞争路线:1)果糖通过HMF中间体的氧化和脱水,和2)醛糖二酸的C2或C5位处的酮形成,以促进呋喃形成。到目前为止,大多数通往FDCA的路线经HMF中间体进行。然而,目前生产FDCA的化学方法需要苛刻的反应条件(例如高温),并且特征在于对所需产物的选择性差。因此,对生产FDCA的新颖、成本效益高的方法存在着持续不断的需求。
本文公开了用于生产FDCA的化学酶方法。一方面,一种产生FDCA的化学酶方法包括将葡萄糖与多酶体系(MES)、酸催化剂和金属催化剂接触,以产生最终的二酸。一方面,所述金属催化剂是非均相的,或者所述金属催化剂是均相的。这种方法的一种情况描述在反应路线I中。参考反应路线I,在这种方法中。使用突变体半乳糖氧化酶(GAO)将D-葡萄糖氧化以形成D-己二醛葡糖。使用吡喃糖-2-氧化酶(POX)将D-己二醛葡糖转变成2-酮基-己二醛葡糖。然后将这种分子在非均相贵金属催化剂上转变成二酸,并使用酸催化剂转变成呋喃形式。高效的环化可能需要二酸而不是二醛,意味着所述非均相催化剂氧化在所述酸催化剂上的反应之前进行。然而,如果情况不是如此并且2-酮基-己二醛葡糖能够以足够高的比例采样到正确的呋喃形式以促进2,5-呋喃二甲醛(DFF)的形成,则所述酸催化剂步骤可以在金属氧化之前进行,如反应路线II中所描绘。
在用于生产FDCA的可选情况下,使用突变体半乳糖氧化酶(GAO)将D-葡萄糖氧化以形成D-己二醛葡糖。随后,通过被称为葡糖二酸脱水酶(GlucD)的酶形成酮基。这被描绘在反应路线III中。这种酶将己二醛葡糖脱水形成5-酮基,同时将4-羟基作为水除去。与反应路线II中描绘的反应循环相似,末端醛的环化和氧化在酸催化剂和非均相贵金属催化剂上进行。环化和末端氧化步骤的顺序可以被颠倒。
在又一种情况下,通过GAO将D-葡萄糖氧化以形成己二醛葡糖。然后可以利用金属催化剂将己二醛葡糖氧化成葡糖二酸以形成5-酮基-4-脱氧-己二醛葡糖,其随后被环化以形成FDCA。这被描绘在反应路线III中。
在又一种情况下,通过POX将D-葡萄糖氧化以形成2-酮基葡萄糖,然后将其环化以形成DFF,然后将后者如前所述氧化以形成FDCA。
这被描绘在反应路线IV中。
本公开的方法是化学酶法,并利用酶、一种或多种酸催化剂和一种或多种金属催化剂的组合。在一种情况下,所述酶包含半乳糖氧化酶、吡喃糖2-氧化酶、葡糖二酸脱水酶、过氧化氢酶或其组合。在一种情况下,所述一种或多种酸催化剂、一种或多种金属催化剂或两者是均相的。在可选情况下,所述一种或多种酸催化剂、一种或多种金属催化剂或两者是非均相的。
在一种情况下,所述MES包含铜自由基氧化酶家族的成员。例如且非限制性的,适合用于本公开的铜自由基氧化酶是半乳糖氧化酶(GAO,EC 1.1.3.9)。GAO是在机制研究和实际应用两方面研究得最广泛的醇氧化酶之一。铜自由基氧化酶家族的其他成员可以适合地用于本公开。
GAO由某些真菌物种特别是禾谷镰刀菌(Fusarium graminearum)(也被称为玉米赤霉(Gibberella zeae))分泌,以通过催化伯醇向醛的氧化同时产生过氧化氢,来帮助细胞外糖类食品来源的降解。GAO的天然功能是将D-半乳糖在C6位置处氧化,以产生D-半乳-己二醛糖。通常将小分子(铁***)或辅助酶(即辣根过氧化物酶或HRP)包括在内以促进GAO活性。通常,HRP以GAO的10重量百分数(重量%)向反应添加。也添加过氧化氢酶以分解过氧化氢。尽管GAO是混杂的,但由于活性位点中的F464和F194与葡萄糖上的赤道C4羟基发生空间冲突,所述天然形式不能与葡萄糖结合。工程化改造GAO以接受D-葡萄糖作为底物来形成C6醛的努力已导致活性提高,如表1中所示。所述M-RQW变体(R330K、Q406T、W290F)显示出1.6U mg-1的比活性。另一种变体Des3-2(Q326E、Y329K、R330K)对葡萄糖的活性是天然酶的四倍。此外,发现突变C383S经由改进与催化性铜离子的结合,通过降低所述酶在非天然底物瓜尔胶和甲基半乳糖上的KM,提高催化效率高达三倍。表1和2提供了一些可能在本公开的方法中有用的GAO突变体的名单。
表1
表2
名称 | 起始突变 | 额外的突变 |
M1 | 野生型 | S10P M70V P136P G195E V494A N535D |
M-RQW | M1 | R330K Q406T W290F I463P |
GAO | M-RQW | C383S |
GAO-mut1 | GAO | Y405F Q406E |
GAO-mut2 | GAO | F194T |
GAO-mut3 | GAO | C383E |
GAO-mut4 | GAO | N245R |
GAO-mut5 | GAO | Q326E Y329K |
在一种情况下,适合用于本公开的GAO可以具有SEQ ID NO.:1至SEQ ID NO.:6中的任一者。
在一种情况下,所述MES包含吡喃糖2-氧化酶(E.C.1.1.3.10)。吡喃糖2-氧化酶(POX)是一种黄素依赖性氧化还原酶,并且是氧化还原酶的葡萄糖-甲醇-胆碱(GMC)超家族的成员。POX氧化包括D-葡萄糖、D-半乳糖和D-木糖在内的几种单糖,并同时将氧还原成过氧化氢。例如,在降解木质纤维素的真菌中,POX在木质素溶解过程中催化α或β-D-葡萄糖向2-酮基葡萄糖的氧化并同时形成过氧化氢。
在真菌中,POX在细胞外与菌丝周质空间中的膜结合囊泡或其他膜结构结合。POX同源物也存在于放线菌、原生细菌和杆菌物种中。来自于单色棉皮孔菌(Spongipellisunicolor)(又称钝头多孔菌(Polyporus obtusus))、黄孢原毛平革菌(Phanerochaetechrysosporium)(PDB 4MIF)、多色栓菌(Trametes multicolor)(又称淡黄褐栓菌(Trametes ochracea)PDB 1TT0))、大隔孢伏革菌(Peniophora gigantea)(PDB 1TZL)、构巢曲霉(Aspergillus nidulans)、米曲霉(A.oryzae)、白囊耙齿菌(Irpex lacteus)、Arthrobacter siccitolerans和Kitasatospora aureofaciens(又称金霉素链霉菌(Streptomyces aureofaciens))的POX酶已被表征。尽管大多数POX酶作为同四聚体存在并且FAD共价结合到组氨酸,但存在例外。POX在溶液中是单体并且非共价结合FAD。KaPOX在溶液中形成二聚体。除了这种氧化酶活性之外,POX还显示出与包括各种不同醌或(络合的)金属离子在内的可选电子受体的显著活性。在一种情况下,适合用于本公开的POX可以具有SEQ ID NO.:7至SEQ ID NO.:11中的任一者。
在一种情况下,所述MES包含葡糖二酸脱水酶(E.C.4.2.1.40)。GluD属于机制多样的烯醇化酶超家族,具体来说是葡糖二酸脱水酶亚组。GluD催化D-葡糖二酸盐和L-艾杜糖二酸盐两者的脱水以形成5-酮基-4-脱氧葡糖二酸盐(KDG),以及两种底物的差向异构化。在第一步中,His 339残基充当作用于D-葡糖二酸盐的C5原子的广义碱,而Lys 207充当作用于相关差向异构体L-艾杜糖二酸盐的广义碱。每个残基与不同的立体选择性功能相关;Lys 207充当S特异性碱,而His 339充当R特异性碱。烯醇阴离子中间体通过与残基Lys 205和Asn 237的氢键以及与催化必需的二价Mg阳离子的相互作用来稳定。
在一种情况下,本公开的MES包含过氧化氢酶(E.C.1.11.1.61)。CAT是存在于所有需氧生物中的一种四聚体、含血红素的抗氧化酶。过氧化氢酶催化H2O2分解成水和氧气。
在一种情况下,所述MES中存在的任何酶是野生型酶、其功能性片段或其功能性变体。当在本文中使用时,“片段”是指包括比全长酶(例如AOX)更短的任何氨基酸序列,但其中所述片段维持足以满足某些用户或过程目标的催化活性。片段可以包括与酶序列的一部分相同的单个连续序列。或者,所述片段可以具有或包括几个不同的较短区段,其中每个区段的氨基酸序列与所述酶的氨基酸序列的不同部分相同,但通过与所述酶的序列不同的氨基酸连接。在本文中,酶的“功能性变体”是指在一个或多个位置处具有保守或非保守的氨基酸***、缺失或替换的多肽,并且其中这些类型的变化中的每一者可以单独发生,或与其他一者或多者组合,在给定顺序中发生一次或多次,但保留催化活性。
在上述突变的可选方案中或与它们组合,所述MES中的酶可以被突变以提高催化活性。可以进行突变以便增强蛋白质或同源物活性,提高蛋白质在产物和/或过氧化氢存在下的稳定性,和提高蛋白质产量。
在本文中,提到了酶的“来源”。应该理解,这是指由指定生物体所表达的生物分子。设想了所述酶可以从所述生物体获得,或者所述酶的一个版本(野生型或重组体)作为适合的构建物提供给适合的表达***。
在一种情况下,本文公开的任何类型的酶都可以被克隆到适合的表达载体中并用于转化表达***的细胞例如大肠杆菌、酵母、毕赤酵母、曲霉、木霉或毁丝霉。“载体”是可以附连另一个DNA区段的复制子,例如质粒、噬菌体、病毒构建物或粘粒。载体被用于在细胞中转导和表达DNA区段。当在本文中使用时,术语“载体”和“构建物”可以包括可以连接或连接有一个或多个基因表达盒的复制子,例如质粒、噬菌体、病毒构建物、粘粒、细菌人工染色体(BAC)、酵母人工染色体(YAC)、人类人工染色体(HAC)等。在本文中,当外源或异源核酸或载体已例如作为与转染试剂的复合物或包装在病毒粒子中而被引入到细胞内时,所述细胞已被这种核酸“转化”。所述转化DNA可以被或可以不被整合(共价连接)到所述细胞的基因组中。
在一种情况下,本文公开的酶的基因作为重组序列被提供在载体中,其中所述序列***作性连接到一个或多个控制或调控序列。“操作性连接”的表达控制序列是指其中所述表达控制序列与所述感兴趣的基因邻接以控制所述感兴趣的基因,以及表达控制序列反式或远距离作用以控制所述感兴趣的基因。
术语“表达控制序列”或“调控序列”可互换使用,并且是指影响与其操作性连接的编码序列的表达所必需的多核苷酸序列。表达控制序列是控制核酸序列的转录、转录后事件和翻译的序列。表达控制序列包括适合的转录起始、终止、启动子和增强子序列,高效的RNA加工信号例如剪接和多聚腺苷酸化信号,稳定细胞质mRNA的序列,提高翻译效率的序列(例如核糖体结合位点),增强蛋白质稳定性的序列,以及在需要时增强蛋白质分泌的序列。此类控制序列的性质因宿主生物体而异;在原核生物中,此类控制序列通常包括启动子、核糖体结合位点和转录终止序列。术语“控制序列”旨在至少包括其存在对于表达必不可少的所有组分,并且还可以包括其存在是有利的其他组分,例如前导序列和融合配偶体序列。
当在本文中使用时,术语“重组宿主细胞”(“表达宿主细胞”、“表达宿主***”、“表达***”或简称为“宿主细胞”)打算是指重组载体已被引入到其中的细胞。应当理解,这些术语意在不仅是指特定的受试细胞,而且是指这种细胞的后代。因为某些修饰可能由于突变或环境影响而在后代中发生,因此这种后代实际上可能与亲代细胞不同,但仍包括在本文所使用的术语“宿主细胞”的范围之内。重组宿主细胞可以是在培养物中生长的分离的细胞或细胞系,或者可以是存在于活组织或生物体中的细胞。
在一种情况下,适合用于本文公开的类型的MES中的酶还可以包括一种或多种纯化的辅因子。在本文中,“辅因子”是指调节酶的生物活性的非蛋白质化合物。许多酶需要辅因子才能正常发挥作用。适合用于本公开的纯化的酶辅因子的非限制性实例包括焦磷酸硫胺素、NAD+、NADP+、磷酸吡哆醛、甲基钴胺素、钴胺素、生物素、辅酶A、四氢叶酸、甲基萘醌、抗坏血酸、黄素单核苷酸、黄素腺嘌呤二核苷酸和辅酶F420。此类辅因子可以包括在MES中和/或在反应过程中的各个不同点添加。在某些情况下,MES中包含的辅因子可以容易地用氧气再生,和/或可以在所述酶的整个生命周期内保持稳定。
在一种或多种情况下,所述MES的任何酶组分以足以为某些用户和/或过程提供所需催化活性的量存在。在这些情况下,本文公开的任何酶可以以所述MES的总重量计约0.0001重量%至约1重量%、或约0.0005重量%至约0.1重量%、或约0.001重量%至约0.01重量%的量存在。
在反应路线I至V中描绘的反应中,所述MES用于最初氧化葡萄糖,其随后反应以形成被脱水的中间体。例如,本公开的方法涉及中间体5-酮基-4-脱氧-葡糖二酸盐、5-酮基-4-脱氧-己二醛葡糖、2-酮基-己二醛葡糖、2-酮基-葡糖二酸和/或2-酮基-葡萄糖的脱水以形成DFF。在一种情况下,脱水在酸催化剂存在下进行。
在一种情况下,所述用于促进上述中间体的脱水的酸催化剂是Bronsted酸或含有以能够在反应混合物中提供质子或水合氢离子为特征的强Bronstead酸位点。适合用于本公开的Bronstead酸包括在葡糖二酸中测试用于呋喃形成的均相酸性催化剂或非均相酸性催化剂。在一种情况下,所述酸催化剂包括离子交换树脂(例如DIAION系列、Amberlyst-15)、磺化二氧化硅、沸石、氧化铌、无机酸例如HCl或其组合。在一种情况下,所述酸催化剂可以以有效催化所述中间体的转化的量存在。在一种情况下,所述酸催化剂存在于适合的溶剂例如二甲基甲酰胺或二甲基亚砜中。例如,所述酸催化剂可以以反应混合物的总重量计约0.1重量%至约0.2重量%或约0.001重量%至约2.0重量%或约0.001重量%至约20重量%的量存在。
在本公开的一种或多种情况下,进行最终的氧化步骤以将醛转变成羧酸,例如在反应路线I至IV中所描绘的。在本公开的一种情况下,所述氧化可以使用金属催化剂或负载型金属催化剂进行。在一种情况下,所述金属催化剂包含负载型金属催化剂例如非均相金属催化剂或均相金属催化剂(HMC)。在一种情况下,催化剂的支撑体(support)包含碳、二氧化硅、氧化铝、二氧化钛(TiO2)、氧化锆(ZrO2)、沸石或其任何组合,其含有以所述支撑体的总重量计少于约1.0重量百分数(重量%)、或少于约0.1重量%或少于约0.01重量%的SiO2粘合剂。
适合的支撑体材料主要是中孔或大孔的,并且基本上不含微孔。例如,所述支撑体可以包含少于约20%的微孔。在一种情况下,所述HMC的支撑体是多孔纳米粒子支撑体。当在本文中使用时,术语“微孔”是指直径<2nm的孔,正如通过氮吸附和汞孔隙度仪法测量并如IUPAC所定义的。当在本文中使用时,术语“中孔”是指直径为约2nm至约50nm的孔,正如通过氮吸附和汞孔隙度仪法测量并如IUPAC所定义的。当在本文中使用时,术语“大孔”是指直径大于50nm的孔,正如通过氮吸附和汞孔隙度仪法测量并如IUPAC所定义的。
在一种情况下,所述HMC支撑体包含平均孔径在约10nm至约100nm范围内,表面积大于约20m2 g-1但小于约300m2 g-1的中孔碳挤出物。适合用于本公开的支撑体可以具有任何适合的形状。例如,所述支撑体可以被成型成0.8-3.0mm的三叶形、四叶形或粒状挤出物。这种成型的支撑体使得能够使用固定滴流床反应器以在连续流动下进行最后的氧化步骤。
在一种情况下,所述HMC包含主族IV、V、VI的金属,或者所述金属来自于副族I、IV、V、VII,或者所述HMC包含金Au。在一种或多种情况下,所述金属包含第8族金属(例如Re、Os、Ir、Pt、Ru、Rh、Pd、Ag)、第3族过渡金属、早期过渡金属或其组合。在可选情况下,脱水催化剂包含在支撑体例如沸石或β-沸石上的铪、钽、锌或其组合。在一种情况下,适合用于本公开的金属催化剂包含金属氧化物、掺杂有碱土元素的氧化锆、稀土正磷酸盐催化剂、钌或其组合。
所述HMC可以使用任何适合的方法来制备。例如,所述HMC可以在大于约200℃至约600℃范围内的温度下,使用用金属盐浸渍的支撑体(例如碳)在氢气中的气相还原来制备。在可选情况下,所述HMC可以在约0℃至约100℃之间的温度下,使用用金属盐浸渍的支撑体浸泡在含氧酸盐(例如甲酸盐、葡萄糖酸盐、柠檬酸盐、乙二醇等)水溶液中的液相还原来制备。或者,可以将所述浸渍的支撑体以非还原形式装载到加氢反应器中,并在启动期间用过程的反应物在线还原。液相还原(LPR)是一种在挤出物的表面环面上获得活性冶金的核壳分散系的合成方法。
在一种情况下,本文公开的类型的材料通过金属前体盐溶液在挤出物支撑体上的初湿含浸或批量吸附,然后在100℃至500℃之间的温度和H2/N2气氛下进行气相还原(GPR)或然后使用碱性水溶液进行液相还原(LPR)来制备。
在一种或多种可选情况下,本公开的方法包括HMF在温和反应条件下的酶氧化,以产生中间体。在一种情况下,本公开的方法还包括将所述中间体用金属催化剂、可选地非均相金属催化剂(HMC)氧化,以产生FDCA。这种反应路线总体描绘在反应路线V中。
不希望受到理论限制,通常为进行的每次氧化产生一分子过氧化氢的氧化酶,可以与利用过氧化氢作为氧化剂来催化另一个氧化的过氧化酶或过氧化物酶组合。这不仅从溶液中除去了高反应性的过氧化氢,而且提供了过氧化酶/过氧化物酶功能所需的过氧化物。
在一种情况下,生产FDCA的方法包括用酶氧化组合物(EOC)对HMF进行酶氧化。在一种情况下,所述EOC包含选自芳基醇氧化酶(AAO)、氯过氧化物酶(CPO)、5-羟甲基糠醛氧化酶(HMFO)、乙二醛氧化酶(GLOX)、周质醛氧化酶(PaoABC)、非特异性过氧化酶(UPO)、辣根过氧化物酶(HRP)、伴有或不伴有激活酶辣根过氧化物酶(HRP)的半乳糖氧化酶(GAO)、乳过氧化物酶(LPO)、髓过氧化物酶(MPO)、嗜酸性粒细胞过氧化物酶(EPO)、甲状腺过氧化物酶(TPO)、卵过氧化物酶、唾液过氧化物酶、钒卤过氧化物酶、非哺乳动物脊椎动物过氧化物酶(POX)、过氧蛋白(Pxd)、细菌过氧素(Pxc)、无脊椎动物过氧连接蛋白(Pxt)和短过氧对接蛋白(PxDo)、短过氧对接蛋白(Pxt)、α-加双氧酶(aDox)、双重氧化酶(DuOx)、***素H合酶、环加氧酶(PGHS/CyOx)、亚油酸二醇合酶(LDS)、其功能性变体的一种或多种酶及其任何组合。本文公开的类型的酶可以从任何适合的来源分离。适合用于本公开的酶的非限制性实例以及它们的催化效率(kcat)呈现在表3中,所述表也提供了可以由所述酶催化的反应路线1的步骤。
表3
在这里,kcat是指周转率、周转频率或周转次数。这个常数表示每单位时间(通常是每分钟或每秒)可以被单个酶分子转变成产物的底物分子的数量。
正如受益于本公开的本领域普通技术人员会理解的,本文公开的类型的反应(例如HMF的AAO氧化)可能导致产生可以不利地影响反应混合物的其他组分的副产物。例如,过氧化氢可能降解EOC的酶,导致催化效率降低。在此类情况下,可以例如通过引入过氧化氢酶(E.C.1.11.1.61)来减轻过氧化氢的不利影响,所述过氧化氢酶不仅降解过氧化氢,而且产生氧气来驱动氧化酶的功能。
在一种情况下,本公开的EOC包含(i)氧化酶;(ii)过氧化物酶;和(iii)过氧化氢酶。可选地,本公开的EOC包含(i)氧化酶、(ii)过氧化酶和(iii)过氧化氢酶;或(i)氧化酶和(ii)过氧化物酶;或(i)氧化酶和(ii)过氧化酶;或氧化酶;或过氧化物酶。这些酶中的每一者可以是本文公开的类型。
在一种情况下,本公开的EOC的一种或多种酶的特征在于kcat等于或大于约9s-1,或者等于或大于约50s-1,或者等于或大于约100s-1。
在一种情况下,本文公开的类型的EOC可用于生产HMF向FDCA的转化中的中间体。可以使用本文公开的类型的EOC生产的中间体的非限制性实例包括二甲酰基呋喃(DFF)、5-羟甲基-2-糠酸(HMFCA)和5-甲酰基-2-呋喃甲酸(FFCA)。在一种情况下,本公开的EOC在与HMF反应时形成选自二甲酰基呋喃(DFF)、5-羟甲基-2-糠酸(HMFCA)和5-甲酰基-2-呋喃甲酸(FFCA)的一种或多种中间体。通过将EOC与HMF反应产生的中间体(例如二甲酰基呋喃)可以用过渡金属催化剂进一步氧化以产生FDCA。
在一种情况下,本文公开的类型的化学酶方法可以在任何适合的反应器中进行。适合的反应器的一种情况描绘在图7中。参考图7,第一酶反应器40可以是喷射泡罩塔、气升柱、搅拌喷射生物反应器或降膜高压氧化容器。反应物葡萄糖和MES可以分别通过管路5和7从储存容器10和20引入到反应器。在一种情况下,酶反应器40可以在低于约100℃的温度或约20℃至约60℃范围内的温度和约1巴至约15巴范围内的压力下运行。在一种情况下,在酶反应器40中,葡萄糖被GAO和HRP酶法转化成D-己二醛葡糖,并存在过氧化氢酶以降解过氧化氢来获得酶的稳定性。此外,酶反应器40可以用压缩空气喷射(以获得分子氧),所述压缩空气可以由空气压缩机30通过管路9供应。尽管未示出,但可以通过添加强酸、碱或缓冲剂来控制pH。来自于酶反应器40的流出物可以通过管路13送往切向流过滤器(TFF)45,以便保留酶反应器中的酶并将其作为渗余物通过管路11再循环,并且D-己二醛葡糖透过物通过管路17进一步流向过程下游到达第二酶反应器60。
第二酶反应器60可以是喷射泡罩塔、气升柱、搅拌喷射生物反应器或降膜高压氧化容器。在一种情况下,第二酶反应器60可以在低于约100℃的温度或约20℃至约60℃范围内的温度和约1巴至约15巴范围内的压力下运行。在第二酶反应器60中,D-己二醛葡糖被POX酶法转化成2-酮基-己二醛葡糖,并存在过氧化氢酶以降解过氧化氢来获得酶的稳定性。在如反应路线III中所描绘的可选方案中,GlucD代替POX。第二酶反应器60可以用压缩空气喷射(以获得分子氧)。尽管未示出,但可以通过添加强酸、碱或缓冲剂来控制pH。来自于第二酶反应器60的流出物可以通过管路21送往TFF 55,以便将酶反应器中的酶作为通过管路19的再循环渗余物保留,并且2-酮基-己二醛葡糖透过物通过管路23进一步流向过程下游到达金属氧化反应器65和脱水反应器70。
在一种情况下,来自于第二酶反应器60的透过物被进料到下游的金属氧化反应器65,在那里2-酮基-己二醛葡糖被转化成2-酮基-葡糖二酸。在一种或多种情况下,氧化反应器65利用本文公开的类型的金属催化剂作为滴流床反应器运行。氧化反应器65可以从顶部进料2-酮基己二醛葡糖并从底部进料高压空气(以提供分子氧),以确保适当的床湿润和传质。氧化反应器65可以在约100℃至约200℃范围内的温度和约10至约100巴范围内的压力下运行。在一种情况下,反应器产物从底部移出并送往脱水反应器70。
离开金属氧化反应器65的2-酮基-葡糖二酸可以在脱水反应器70中通过脱水转化成FDCA。在一种情况下,脱水反应器70以上游或下游配置运行。正如前文中描述的,脱水反应器70可以装有固定化的强酸交换催化剂。脱水反应器70可以在约160℃至约200℃范围内的温度下运行。例如,脱水反应可以在高压下与液态水发生。
在一种情况下,所述脱水反应器的产物包括水和FDCA的混合物,以及副产物杂质。脱水反应器产物料流可以通过管路37转移到由水结晶装置75、溶剂结晶装置80和Nustche过滤器85组成的纯化组列。由于FDCA在水中的溶解性随着温度强烈变化,因此水结晶装置75可以是冷却结晶器或冷却和真空结晶器。在一种情况下,FDCA晶体随后通过过滤分离并送往第二个有机溶剂结晶器。
在有机溶剂结晶器80中,所述溶剂可以是1-丁醇、异丁醇、甲醇或另一种适合的有机溶剂。不希望受到理论限制,通过在水和有机溶剂之间切换,可以除去母液中的不同杂质。然后通过冷却或真空结晶结晶出FDCA,除去晶体并通过Nutsche过滤器85。有机溶剂可以通过蒸馏除去并再生,以除去非挥发性杂质。
然后将FDCA晶体在Nutsche过滤器85中洗涤以去除任何残留杂质。可以使用极性非质子溶剂如乙腈,因为(1)这会溶解以前在水这种极性质子溶剂或1-丁醇这种非极性质子溶剂中没有拣出的杂质,以及(2)FDCA仅微溶于乙腈。离开Nutsche过滤器85的乙腈然后可以通过蒸馏再生,以去除非挥发性杂质。然后从Nutsche过滤器85取出高纯度FDCA晶体作为最终产物。
尽管上图是PFD级别的详细图,但并未示出所有过程互连,例如倒溢、阻塞和排放阀、再循环管线、控制阀、冷却/加热元件、泵、中间罐、消泡剂等。
在一种情况下,本文公开的方法导致制备高纯度的FDCA。所述FDCA可以具有高于约80%或高于约85%或高于约95%,或约80%至约99%或约85%至约99%或约90%至约99%的纯度。
其他公开内容
提供了本公开的下述列举的方面作为非限制性实例。
第一方面是一种用于制备2,5-呋喃二甲酸的化学酶方法,所述方法包括:将D-葡萄糖与(i)选自基本上由半乳糖氧化酶、吡喃糖2-氧化酶、葡糖二酸脱水酶、过氧化氢酶组成的组的至少两种酶及其组合接触,以产生中间体;和(ii)将所述中间体与金属催化剂和酸催化剂接触,以形成2,5-呋喃二甲酸。
第二方面是所述第一方面的化学酶方法,其中将D-葡萄糖与半乳糖氧化酶和过氧化氢酶接触以形成D-己二醛葡糖;并且其中所述方法还包括:将D-己二醛葡糖与吡喃糖-2-氧化酶和过氧化氢酶在适合于形成2-酮基-己二醛葡糖的条件下接触;将2-酮基-己二醛葡糖与非均相金属催化剂接触,以形成2-酮基-葡糖二酸;和将2-酮基葡糖二酸在酸催化剂存在下脱水,以形成2,5-呋喃二甲酸。
第三方面是所述第一至第二方面中的任一者的化学酶方法,其中将D-葡萄糖与半乳糖氧化酶和过氧化氢酶接触以形成D-己二醛葡糖;并且其中所述方法还包括:将D-己二醛葡糖与吡喃糖-2-氧化酶和过氧化氢酶在适合于形成2-酮基-己二醛葡糖的条件下接触;将2-酮基-己二醛葡糖用酸催化剂脱水,以形成2,5-呋喃二甲醛;和将2,5-呋喃二甲醛在非均相金属催化剂存在下氧化,以形成2,5-呋喃二甲酸。
第四方面是所述第一至第三方面中的任一者的化学酶方法,其中将D-葡萄糖与半乳糖氧化酶和过氧化氢酶接触以形成D-己二醛葡糖;并且其中所述方法还包括:将D-己二醛葡糖与金属催化剂接触,以形成D-葡糖二酸;将D-葡糖二酸用葡糖二酸脱水酶脱水,以形成5-酮基-4-脱氧己二醛葡糖;和将5-酮基-4-脱氧己二醛葡糖在酸催化剂存在下环化,以形成2,5-呋喃二甲酸。
第五方面是所述第一至第四方面中的任一者的化学酶方法,其中将D-葡萄糖与吡喃糖-2-氧化酶和过氧化氢酶接触以形成2-酮基-葡萄糖;并且其中所述方法还包括:将2-酮基-葡萄糖用酸催化剂在适合于形成2,5-呋喃二甲醛的条件下脱水;将5-酮基-4-脱氧己二醛葡糖用酸催化剂脱水,以形成2,5-呋喃二甲醛;和将2,5-呋喃二甲醛在非均相金属催化剂存在下氧化,以形成2,5-呋喃二甲酸。
第六方面是所述第一至第五方面中的任一者的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1至SEQ ID NO.:6中的任一者。
第七方面是所述第二方面的化学酶方法,其中所述半乳糖氧化酶具有SEQ IDNO.:1至SEQ ID NO.:6中的任一者。
第八方面是所述第三方面的化学酶方法,其中所述半乳糖氧化酶具有SEQ IDNO.:1至SEQ ID NO.:6中的任一者。
第九方面是所述第四方面的化学酶方法,其中所述半乳糖氧化酶具有SEQ IDNO.:1至SEQ ID NO.:6中的任一者。
第十方面是所述第五方面的化学酶方法,其中所述半乳糖氧化酶具有SEQ IDNO.:1至SEQ ID NO.:6中的任一者。
第十一方面是所述第一至第五方面中的任一者的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1。
第十二方面是所述第一至第十一方面中的任一者的化学酶方法,其中所述丙酮酸-2-氧化酶具有SEQ ID NO.:7至SEQ ID NO.:11中的任一者。
第十三方面是所述第一至第十二方面中的任一者的化学酶方法,其在低于约100℃的温度下进行。
第十四方面是所述第一至第十三方面中的任一者的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
第十五方面是所述第二方面的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
第十六方面是所述第三方面的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
第十七方面是所述第四方面的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
第十八方面是所述第五方面的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
第十九方面是所述第一至第十八方面中的任一者的化学酶方法,其中所述非均相金属催化剂含有包含碳、二氧化硅、氧化铝、二氧化钛(TiO2)、氧化锆(ZrO2)、沸石或其任何组合的支撑体。
第二十方面是所述第一至第十九方面中的任一者的化学酶方法,其中所述酸催化剂、金属催化剂或两者是非均相的。
第二十一方面是所述第一至第二十方面中的任一者的化学酶方法,其中所述酸催化剂、金属催化剂或两者是均相的。
第二十二方面是一种用于制备2,5-呋喃二甲酸的化学酶方法,所述方法包括:使用酶氧化组合物对5-羟甲基糠醛进行酶氧化以形成中间体,所述组合物包含选自芳基醇氧化酶(AAO)、氯过氧化物酶(CPO)、5-羟甲基糠醛氧化酶(HMFO)、乙二醛氧化酶(GLOX)、周质醛氧化酶(PaoABC)、非特异性过氧化酶(UPO)、辣根过氧化物酶(HRP)、伴有或不伴有激活酶辣根过氧化物酶(HRP)的半乳糖氧化酶(GAO)、乳过氧化物酶(LPO)、髓过氧化物酶(MPO)、嗜酸性粒细胞过氧化物酶(EPO)、甲状腺过氧化物酶(TPO)、卵过氧化物酶、唾液过氧化物酶、钒卤过氧化物酶、非哺乳动物脊椎动物过氧化物酶(POX)、过氧蛋白(Pxd)、细菌过氧素(Pxc)、无脊椎动物过氧连接蛋白(Pxt)和短过氧对接蛋白(PxDo)、短过氧对接蛋白(Pxt)、α-加双氧酶(aDox)、双重氧化酶(DuOx)、***素H合酶或环加氧酶(PGHS/CyOx)、亚油酸二醇合酶(LDS)、其功能性变体的一种或多种酶及其任何组合;和使用金属催化剂氧化所述中间体,以形成2,5-呋喃二甲酸。
第二十三方面是所述第二十二方面的化学酶方法,其中所述酶氧化在低于约100℃的温度下进行。
第二十四方面是所述第二十二至第二十三方面中的任一者的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
第二十五方面是所述第一至第二十四方面中的任一者的化学酶方法,其还包括对所述2,5-呋喃二甲酸进行水结晶、溶剂结晶和Nutsche过滤。
实施例
目前公开的主题内容已被概括性描述,下面的实施例被给出作为所述主题内容的特定情况并展示其实践和优点。应该理解,所述实施例作为说明给出,并且不打算以任何方式限制本说明书或权利要求书。
实施例1
评估了来自于表1的突变体对葡萄糖的比活性,结果呈现在图1中。工程化改造了能够将葡萄糖转化成己二醛葡糖的另一个GAO突变体。在定向进化和合理酶工程化改造后,所述改进的GAO突变体对葡萄糖表现出35U mg-1的比活性。对含有下述添加的突变的母体序列进行了在催化性铜的10之内的30个位点的定向进化:1)R330、Q406T、W290F;2)C383S;和3)Y405F和Q406E。发现表4中描述的其他突变对产生己二醛葡糖的活性具有中性或不利影响。我们将所述新的组合序列命名为GAO-Mut1。所述表达的构建物的完整序列作为SEQID No.1给出,其含有用于在大肠杆菌中表达和纯化的“MGHHHHHHSSGHIEGRHM”N-端his标签和连接物。
使用含有NNS密码子的引物,通过QUIKCHANGE方法将GAO-Mut1中的选定位置突变成所有20种氨基酸。然后以下述方式筛选构建物:挑取菌落并用于各自接种到装有溶原肉汤(LB)的96孔深孔板中的一个孔。然后将生长的克隆用于接种单独的96孔深孔板中的自诱导培养基,用于蛋白质表达。将收获的细胞用细菌蛋白提取试剂(B-PER)裂解,然后使用检测过氧化氢的比色ABTS测定法筛选裂解液的氧化酶活性。
简而言之,在暴露和不暴露于热的情况下测定裂解液的活性。为了在不存在热激惹的情况下测定活性,将裂解液稀释50倍。将体积为5μL的稀释的裂解液与ABTS测定溶液合并(终浓度为2%w/v葡萄糖、0.0125mg/ml辣根过氧化物酶、50mM pH 8的磷酸钠缓冲液、0.05%ABTS)至终体积为200μL,并监测405nm处吸光度的变化,直至反应完成。为了测定热激惹后的残留活性,将50μL裂解液在50℃温育10分钟,将20μL热处理过的裂解液添加到ABTS溶液,然后监测405nm处吸光度的变化。使用曲线的线性部分测量ΔA405/min并取ABTS在405nm处的消光系数为36.8mM-1cm-1,从下述公式计算比活性。
选择表现出比GAO-Mut1更高的ΔA405/min的突变体裂解液用于进一步表征。在通过DNA测序鉴定突变后,将命中物表达、纯化、测定比活性,并通过观察到最大活性的一半时的温度(T50)来评估热稳定性。突变体从24孔板中使用自诱导培养基的5ml培养物纯化。将收获的细胞用B-PER裂解,并将裂解液以15,000相对离心力(rcf)在4℃离心30min。将裂解液上清液用于使用HisPurTM Ni-NTA离心板的蛋白质纯化。将洗脱的蛋白质样品用含有0.5mMCuSO4的100mM pH 7.5的磷酸钾缓冲液稀释,并使用ABTS测定法测量比活性。通过将蛋白质在不存在底物的情况下加热,冷却,然后使用ABTS测定法测量残留活性,来测量T50。通过将蛋白质在一定体积的100mM pH 7.5磷酸盐缓冲液中稀释到2.5mg/L的浓度,等分50μL到96孔PCR板的一排中,并在足以捕获最高和最低酶性能的温度梯度下温育10分钟,来完成加热。在加热后迅速将混合物在冰上冷却,并如上所述测量20μL酶溶液在终体积为200μL的ABTS溶液中的ΔA405/min。
将命中物纯化,测试活性和T50,并且重组以产生来自于定向进化步骤的最终最佳突变体。包括A193R、D404H、F441Y、A172V在内的可以在Mut1背景中有益地组合的有希望的点突变列于表4中。将这些突变组合在名为GAO-Mut47的单个组合突变体中,其表现出27.3Umg-1的比活性和56.8℃的T50。表3提供了所进行的点突变的名单以及它们的特征。
表4
实施例2
使用基于结构的计算方法和多序列比对数据(MSA)的结合,实现了GAO的合理工程化改造,以进一步接受葡萄糖底物并鉴定稳定化突变。鉴定到GAO-M-RQW-S可以接受葡萄糖和葡萄糖酸盐两者作为底物,结果展示在图2中。合理设计在GAO-M-RQW-S序列而不是GAO-Mut1上进行。使用的结构方法包括将FoldX55(40个预测突变)和PROSS56(80个突变)应用于蛋白质数据库(PDB)结构2WQ8的改良形式,以包含GAO-M-RQW-S突变。将基于MSA的预测应用于185个成员的MSA。这个MSA从使用JALVIEW选取的1000个序列的初始集生成,以除去具有98%冗余度的序列并且只保留经实验验证为糖类氧化酶的序列。将在设计用于合成HIV药物Islatravir的中间体的GAO中鉴定到的30个突变也添加到所述评估组中。
总的来说,使用与上述用于筛选定向进化克隆相同的方法筛选了202个点突变。从初筛鉴定到39个命中物,并从第二轮筛选中重新鉴定出16个命中物。在来自于定向进化步骤的最佳组合突变体(GAO-Mut47)中产生组合突变体后,鉴定到突变N66S、S306A、S311F和Q486L是互补且有益的,而N28I、Y189W、S331R、A378D和R459Q在这种背景下被视为有害。结果概述在表5中。最终的含有Mut47突变和N66S、S306A、S311F和Q486L的GAO-Mut107构建物对2%葡萄糖表现出34.96U mg-1的比活性和60.56℃的T50,如图3中所示。在晚些时候并入了从机器学习算法鉴定的额外的突变,以产生GAO-mut142和GAO-mut164。
表5
粗体突变在Mut47背景A193R D404H F441Y A172V中有益
a在来自于其他数据的独立实验中收集的数据。提高倍数与内部对照Mut47相比来计算。
b在来自于其他数据的独立实验中收集的数据。提高倍数与内部对照Mut47相比来计算。
实施例3
在加压至100psi的200mL容器中进行50ml反应。所述容器装有50mM pH 8的磷酸钠缓冲液、50μM CuSO4、15w/v%葡萄糖、0.005w/v%过氧化氢酶、0.001%辣根过氧化物酶和0.001w/v%工程化GAO。将所述反应在500rpm、11℃下搅拌48小时。在0、24和48小时取样,然后使用HPLC测定以测量残留葡萄糖,结果呈现在图4中。起始原料的量在48小时内从15下降到5.7%(w/v)。
实施例4
通过POX从己二醛葡糖生产2-酮基-己二醛葡糖
为了确定POX怎样可以将D-葡萄糖或D-己二醛葡糖转化成在反应路线III的情形中有用的产物,获得了可商购的POX酶并用于2,2'-连氮基-双(3-乙基苯并噻唑膦-6-磺酸)(ABTS)比色反应中,所述反应使用50mM pH 6的磷酸钾缓冲液中的浓度为20mM的D-葡萄糖、D-己二醛葡糖、2-酮基-D-葡萄糖酸盐、2-酮基-D-葡萄糖或5-酮基-D-葡萄糖,在室温下进行。在测定中包括已知将葡萄糖在C1位处氧化成葡萄糖酸内酯的葡萄糖氧化酶(GOX)和GAO突变体作为对照。简单来说,制备4x储用溶液,并稀释到最终反应浓度为20mM底物、0.025mg/ml辣根过氧化物酶(HRP)、50mM pH 6的磷酸钾缓冲液和0.1%(w/v)ABTS。将该溶液与酶合并至终浓度为0.8μg/mL以开始反应并温育25分钟,同时在微孔板读板器中监测A405。比活性被计算为:
活性筛选的结果证实了使用POX从己二醛葡糖生成2-酮基-己二醛葡糖的潜力。POX对己二醛葡糖表现出8.8U/mg的比活性(对天然底物葡萄糖的性能的77%)。这种比活性可以通过工程化改造来提高。结果示出在表6和图5中。2-酮基葡萄糖、2-酮基葡萄糖酸盐、5-酮基葡萄糖酸盐不是POX的底物。所有GAO酶对2-酮基-葡萄糖均没有活性。考虑到这个数据,2-酮基-己二醛葡糖的生产在双反应器***中应是可行的,其中底物通过装有GAO的第一反应器以产生己二醛葡糖,然后通过装有POX的第二反应器以生成2-酮基-己二醛葡糖。通过单一酶氧化反应器的生产要求工程化改造能够接受2-酮基-己二醛葡糖作为底物的GAO。正如预期,GOX对天然底物葡萄糖表现出高活性。
表6
通过HPLC-MS探测产物概况。使用下述方法分析含有0.1%(w/v)POX、10%(w/v)底物、0.005%(w/v)过氧化氢酶和80mM pH 6.0的磷酸钾缓冲液的96孔微量滴定板中的50μL反应:
流动相A:50mM甲酸铵+1%甲酸水溶液
流动相B:1%甲酸的乙腈溶液
柱温:50℃
柱:Torus 2-Pic 1.7μm,3.0mm x 150mm
所选的离子监测:进行173、175、177、179、193和195
锥电压:默认值
定时方法呈现在表7中。
表7
时间 | 流速(mL/min) | %A | %B |
0 | 0.8 | 30 | 70 |
3 | 0.8 | 80 | 20 |
4 | 0.8 | 80 | 20 |
5 | 0.8 | 30 | 70 |
5.1 | 0.8 | 30 | 70 |
7 | 0.8 | 30 | 70 |
对应于预期的2-酮基-己二醛葡糖产物的175m/z通道中的峰在早至54分钟时就被检测到,并且随着己二醛葡糖(177m/z)的消失继续增大。这些结果呈现在图6中。负离子模式下的质量通道从上至下对应于173、175、177、179、193、195m/z。对于0.9、1.6或2.8hr的葡萄糖反应,未示出173m/z通道。
己二醛葡糖通常在177m/z通道中表现出三个峰,潜在地对应于所述化合物的不同环化形式。令人好奇的是,保留时间最长的己二醛葡糖峰比其他峰消失得更慢,表明POX可能偏好底物的某些构型超过其他构型。一些峰出现在193m/z通道中,其可能对应于葡萄糖醛酸根或葡萄糖醛酸。
尽管已经示出并描述了当前公开的主题内容的多个方面,但本领域技术人员可以在不背离主题内容的精神和教导的情况下对其进行修改。本文所述的方面仅是示例性的,并不打算进行限制。本文公开的主题内容的许多变化和修改是可能的,并且在所公开的主题内容的范围之内。在明确陈述数值范围或限度的情况下,此类明确的范围或限度应该被理解为包括落入明确陈述的范围或限度之内的相似量级的迭代的范围或限度(例如,约1至约10包括2、3、4等;大于0.10包括0.11、0.12、0.13等)。对于权利要求项的任何要素使用术语“任选地”旨在意味着所述主题要素是必需的或者不是必需的。两种可选方案都打算在所述权利要求项的范围之内。更广泛的术语例如包含、包括、具有等的使用,应该被理解为为更狭义的术语例如由……组成、基本上由……组成、基本上由……构成等提供支持。
因此,保护范围不受上述描述的限制,而仅受权利要求书的限制,该范围包括权利要求书的主题内容的所有等同物。每个权利要求项都作为本公开的一个方面并入说明书中。因此,权利要求书是进一步的描述并且是对本发明的方面的补充。本文对参考文献的讨论并不承认它是当前公开的主题内容的先有技术,尤其是任何出版日期可能在本申请的优先权日期之后的参考文献。本文引用的所有专利、专利申请和出版物的公开内容通过参考并入本文,只要它们提供了对本文所述内容的示例性、程序性或其他细节的补充。
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Pro Lys Pro Pro His Thr Tyr Thr Ile Asp Met Lys Thr Thr Gln Asn
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Ile Thr Leu Gly Glu Pro Gly Thr Ser Pro Asn Thr Val Phe Ala Ser
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Thr Leu Thr Asn Asn Gly Gly Asn Ser Tyr Ser Phe Gln Val Pro Ser
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Thr Cys Asp Ser Ala Gln Ser Gly Asn Glu Cys Asn Lys Ala Ile Asp
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Gly Asn Lys Asp Thr Phe Trp His Thr Phe Tyr Gly Ala Asn Gly Asp
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Pro Lys Pro Pro His Thr Tyr Thr Ile Asp Met Lys Thr Thr Gln Asn
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Val Ser Gly Leu Ser Val Leu Pro Arg Gln Asp Gly Asn Gln Asn Gly
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Gly Lys Arg Gln Ser Asn Arg Gly Val Ala Pro Asp Ala Met Ser Gly
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Gly Ser Pro Asp Tyr Thr Asp Ser Asp Ala Thr Thr Asn Ala His Ile
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Asn Gly Leu Tyr Phe Ala Arg Thr Phe His Thr Ser Val Val Leu Pro
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Asp Thr Phe Tyr Lys Gln Asn Pro Asn Ser Ile Val Arg Ala Tyr His
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Gly Leu Cys Gly Asp Cys Thr Thr Asn His Phe Asp Ala Gln Ile Phe
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Thr Pro Asn Tyr Leu Tyr Asp Ser Asn Gly Asn Leu Ala Thr Arg Pro
530 535 540
Lys Ile Thr Arg Thr Ser Thr Gln Ser Val Lys Val Gly Gly Arg Ile
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Thr Ile Ser Thr Asp Ser Ser Ile Ser Lys Ala Ser Leu Ile Arg Tyr
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Gly Thr Ala Thr His Thr Val Asn Thr Asp Gln Arg Arg Ile Pro Leu
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Thr Leu Thr Asn Asn Gly Gly Asn Ser Tyr Ser Phe Gln Val Pro Ser
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Asp Ser Gly Val Ala Leu Pro Gly Tyr Trp Met Leu Phe Val Met Asn
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Ser Ala Gly Val Pro Ser Val Ala Ser Thr Ile Arg Val Thr Gln
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Thr Cys Asp Ser Ala Gln Ser Gly Asn Glu Cys Asn Lys Ala Ile Asp
20 25 30
Gly Asn Lys Asp Thr Phe Trp His Thr Phe Tyr Gly Ala Asn Gly Asp
35 40 45
Pro Lys Pro Pro His Thr Tyr Thr Ile Asp Met Lys Thr Thr Gln Asn
50 55 60
Val Ser Gly Leu Ser Val Leu Pro Arg Gln Asp Gly Asn Gln Asn Gly
65 70 75 80
Trp Ile Gly Arg His Glu Val Tyr Leu Ser Ser Asp Gly Thr Asn Trp
85 90 95
Gly Ser Pro Val Ala Ser Gly Ser Trp Phe Ala Asp Ser Thr Thr Lys
100 105 110
Tyr Ser Asn Phe Glu Thr Arg Pro Ala Arg Tyr Val Arg Leu Val Ala
115 120 125
Ile Thr Glu Ala Asn Gly Gln Pro Trp Thr Ser Ile Ala Glu Ile Asn
130 135 140
Val Phe Gln Ala Ser Ser Tyr Thr Ala Pro Gln Pro Gly Leu Gly Arg
145 150 155 160
Trp Gly Pro Thr Ile Asp Leu Pro Ile Val Pro Val Ala Ala Ala Ile
165 170 175
Glu Pro Thr Ser Gly Arg Val Leu Met Trp Ser Ser Trp Arg Asn Asp
180 185 190
Ala Phe Glu Gly Ser Pro Gly Gly Ile Thr Leu Thr Ser Ser Trp Asp
195 200 205
Pro Ser Thr Gly Ile Val Ser Asp Arg Thr Val Thr Val Thr Lys His
210 215 220
Asp Met Phe Cys Pro Gly Ile Ser Met Asp Gly Asn Gly Gln Ile Val
225 230 235 240
Val Thr Gly Gly Asn Asp Ala Lys Lys Thr Ser Leu Tyr Asp Ser Ser
245 250 255
Ser Asp Ser Trp Ile Pro Gly Pro Asp Met Gln Val Ala Arg Gly Tyr
260 265 270
Gln Ser Ser Ala Thr Met Ser Asp Gly Arg Val Phe Thr Ile Gly Gly
275 280 285
Ser Phe Ser Gly Gly Val Phe Glu Lys Asn Gly Glu Val Tyr Ser Pro
290 295 300
Ser Ala Lys Thr Trp Thr Phe Leu Pro Asn Ala Lys Val Asn Pro Met
305 310 315 320
Leu Thr Ala Asp Lys Gln Gly Leu Tyr Lys Arg Asp Asn His Ala Trp
325 330 335
Leu Phe Gly Trp Lys Lys Gly Ser Val Phe Gln Ala Gly Pro Ser Thr
340 345 350
Ala Met Asn Trp Tyr Tyr Thr Ser Gly Ser Gly Asp Val Lys Ser Ala
355 360 365
Gly Lys Arg Gln Ser Asn Arg Gly Val Asp Pro Asp Ala Met Ser Gly
370 375 380
Asn Ala Val Met Tyr Asp Ala Val Lys Gly Lys Ile Leu Thr Phe Gly
385 390 395 400
Gly Ser Pro Asp Tyr Thr Asp Ser Asp Ala Thr Thr Asn Ala His Ile
405 410 415
Ile Thr Leu Gly Glu Pro Gly Thr Ser Pro Asn Thr Val Phe Ala Ser
420 425 430
Asn Gly Leu Tyr Phe Ala Arg Thr Phe His Thr Ser Val Val Leu Pro
435 440 445
Asp Gly Ser Thr Phe Ile Thr Gly Gly Gln Arg Arg Gly Ile Pro Phe
450 455 460
Glu Asp Ser Thr Pro Val Phe Thr Pro Glu Ile Tyr Val Pro Glu Gln
465 470 475 480
Asp Thr Phe Tyr Lys Leu Asn Pro Asn Ser Ile Val Arg Ala Tyr His
485 490 495
Ser Ile Ser Leu Leu Leu Pro Asp Gly Arg Val Phe Asn Gly Gly Gly
500 505 510
Gly Leu Cys Gly Asp Cys Thr Thr Asn His Phe Asp Ala Gln Ile Phe
515 520 525
Thr Pro Asn Tyr Leu Tyr Asp Ser Asn Gly Asn Leu Ala Thr Arg Pro
530 535 540
Lys Ile Thr Arg Thr Ser Thr Gln Ser Val Lys Val Gly Gly Arg Ile
545 550 555 560
Thr Ile Ser Thr Asp Ser Ser Ile Ser Lys Ala Ser Leu Ile Arg Tyr
565 570 575
Gly Thr Ala Thr His Thr Val Asn Thr Asp Gln Arg Arg Ile Pro Leu
580 585 590
Thr Leu Thr Asn Asn Gly Gly Asn Ser Tyr Ser Phe Gln Val Pro Ser
595 600 605
Asp Ser Gly Val Ala Leu Pro Gly Tyr Trp Met Leu Phe Val Met Asn
610 615 620
Ser Ala Gly Val Pro Ser Val Ala Ser Thr Ile Arg Val Thr Gln
625 630 635
<210> 6
<211> 638
<212> PRT
<213> 合成的
<400> 6
Ala Ser Ala Pro Ile Gly Ser Ala Ile Pro Arg Asn Asn Trp Ala Val
1 5 10 15
Thr Cys Asp Ser Ala Gln Ser Gly Asn Glu Cys Asn Lys Ala Ile Asp
20 25 30
Gly Asn Lys Asp Thr Phe Trp His Thr Phe Tyr Gly Ala Asn Gly Pro
35 40 45
Lys Pro Pro His Thr Tyr Thr Ile Asp Met Lys Thr Thr Gln Asn Val
50 55 60
Ser Gly Leu Ser Val Leu Pro Arg Gln Asp Gly Asn Gln Asn Gly Trp
65 70 75 80
Ile Gly Arg His Glu Val Tyr Leu Ser Ser Asp Gly Thr Asn Trp Gly
85 90 95
Ser Pro Val Ala Ser Gly Ser Trp Phe Ala Asp Ser Thr Thr Lys Tyr
100 105 110
Ser Asn Phe Glu Thr Arg Pro Ala Arg Tyr Val Arg Leu Val Ala Ile
115 120 125
Thr Glu Ala Asn Gly Gln Pro Trp Thr Ser Ile Ala Glu Ile Asn Val
130 135 140
Phe Gln Ala Ser Ser Tyr Thr Ala Pro Gln Pro Gly Leu Gly Arg Trp
145 150 155 160
Gly Pro Thr Ile Asp Leu Pro Ile Val Pro Val Ala Ala Ala Ile Glu
165 170 175
Pro Thr Ser Gly Arg Val Leu Met Trp Ser Ser Tyr Arg Asn Asp Arg
180 185 190
Phe Glu Gly Ser Pro Gly Gly Ile Thr Leu Thr Ser Ser Trp Asp Pro
195 200 205
Ser Thr Gly Ile Val Ser Asp Arg Thr Val Thr Val Thr Lys His Asp
210 215 220
Met Phe Cys Pro Gly Ile Ser Met Asp Gly Asn Gly Gln Ile Val Val
225 230 235 240
Thr Gly Gly Asn Asp Ala Lys Lys Thr Ser Leu Tyr Asp Ser Ser Ser
245 250 255
Asp Ser Trp Ile Pro Gly Pro Asp Met Gln Val Ala Arg Gly Tyr Gln
260 265 270
Ser Ser Ala Thr Met Ser Asp Gly Arg Val Phe Thr Ile Gly Gly Ser
275 280 285
Phe Ser Gly Gly Val Phe Glu Lys Asn Gly Glu Val Tyr Ser Pro Ser
290 295 300
Ala Lys Thr Trp Thr Phe Leu Pro Asn Ala Lys Val Asn Pro Met Leu
305 310 315 320
Thr Ala Asp Lys Gln Gly Leu Tyr Lys Ser Asp Asn His Ala Trp Leu
325 330 335
Phe Gly Trp Lys Lys Gly Ser Val Phe Gln Ala Gly Pro Ser Thr Ala
340 345 350
Met Asn Trp Tyr Tyr Thr Ser Gly Ser Gly Asp Val Lys Ser Ala Gly
355 360 365
Lys Arg Gln Ser Asn Arg Gly Val Ala Pro Asp Ala Met Ser Gly Asn
370 375 380
Ala Val Met Tyr Asp Ala Val Lys Gly Lys Ile Leu Thr Phe Gly Gly
385 390 395 400
Ser Pro His Phe Glu Asp Ser Asp Ala Thr Thr Asn Ala His Ile Ile
405 410 415
Thr Leu Gly Glu Pro Gly Thr Ser Pro Asn Thr Val Phe Ala Ser Asn
420 425 430
Gly Leu Tyr Phe Ala Arg Thr Tyr His Thr Ser Val Val Leu Pro Asp
435 440 445
Gly Ser Thr Phe Ile Thr Gly Gly Gln Arg Arg Gly Ile Pro Phe Glu
450 455 460
Asp Ser Thr Pro Val Phe Thr Pro Glu Ile Tyr Val Pro Glu Gln Asp
465 470 475 480
Thr Phe Tyr Lys Gln Asn Pro Asn Ser Ile Val Arg Ala Tyr His Ser
485 490 495
Ile Ser Leu Leu Leu Pro Asp Gly Arg Val Phe Asn Gly Gly Gly Gly
500 505 510
Leu Cys Gly Asp Cys Thr Thr Asn His Phe Asp Ala Gln Ile Phe Thr
515 520 525
Pro Asn Tyr Leu Tyr Asp Ser Asn Gly Asn Leu Ala Thr Arg Pro Lys
530 535 540
Ile Thr Arg Thr Ser Thr Gln Ser Val Lys Val Gly Gly Arg Ile Thr
545 550 555 560
Ile Ser Thr Asp Ser Ser Ile Ser Lys Ala Ser Leu Ile Arg Tyr Gly
565 570 575
Thr Ala Thr His Thr Val Asn Thr Asp Gln Arg Arg Ile Pro Leu Thr
580 585 590
Leu Thr Asn Asn Gly Gly Asn Ser Tyr Ser Phe Gln Val Pro Ser Asp
595 600 605
Ser Gly Val Ala Leu Pro Gly Tyr Trp Met Leu Phe Val Met Asn Ser
610 615 620
Ala Gly Val Pro Ser Val Ala Ser Thr Ile Arg Val Thr Gln
625 630 635
<210> 7
<211> 531
<212> PRT
<213> Pseudarthrobacter phenanthrenivorans
<400> 7
Met Ser Gly His Arg Tyr Pro Ala Ala Val Asp Val Ala Ile Val Gly
1 5 10 15
Ser Gly Pro Thr Ala Ser Ala Tyr Ala Arg Ile Leu Ser Glu Glu Ala
20 25 30
Pro Gly Ala Thr Ile Ala Met Phe Glu Val Gly Pro Thr Val Ser Ile
35 40 45
Pro Pro Gly Ala His Val Lys Asn Ile Glu Asp Pro Glu Arg Arg Ser
50 55 60
Ser Ala Gln Arg Ala Ser Glu Gly Pro Gly Ala Gly Ala Glu Thr Val
65 70 75 80
Ser Ser Pro Gly Ala Val Lys Ser Gly Glu Arg Arg Ala Arg Pro Gly
85 90 95
Thr Tyr Leu Leu Gln Asp Gly Tyr Ala Phe Pro Gly Glu Asp Gly Met
100 105 110
Pro Val Ala Ala Met Ser Ser Asn Val Gly Gly Met Ala Ala His Trp
115 120 125
Thr Ala Ala Cys Pro Arg Pro Gly Gly Lys Glu Arg Ile Pro Phe Leu
130 135 140
Pro Asp Leu Glu Asp Leu Leu Asp Asp Ala Asp Arg Leu Leu Gly Val
145 150 155 160
Thr Thr His Ala Phe Asp Gly Ala Pro Phe Ser Asp Leu Val Arg Glu
165 170 175
Arg Leu Ala Ala Val Val Asp Asn Gly Arg Gly Pro Ala Phe Arg Val
180 185 190
Gln Pro Met Pro Leu Ala Val His Arg Arg Glu Asp Gly Gly Leu Val
195 200 205
Trp Ser Gly Ser Asp Val Val Met Gly Asp Val Thr Arg Glu Asn Pro
210 215 220
Gln Phe His Leu Phe Asp Glu Ser Leu Val Thr Arg Val Leu Val Glu
225 230 235 240
Asp Gly Val Ala Ala Gly Val Glu Val Gln Asp Arg Arg Thr Gly Gly
245 250 255
Thr His Gln Val Ser Ala Arg Tyr Val Val Val Gly Ala Asp Ala Leu
260 265 270
Arg Thr Pro Gln Leu Leu Trp Ala Ser Gly Ile Arg Pro Asp Ala Leu
275 280 285
Gly Arg Tyr Leu Asn Asp Gln Ala Gln Val Val Phe Ala Ser Arg Leu
290 295 300
Arg Gly Val Thr Ala Pro Gln Gly Ser Ala Ala Ala Asp Gly Ala Leu
305 310 315 320
Ser Glu Gln Ser Gly Val Ala Trp Val Pro Tyr Thr Asp Glu Ala Pro
325 330 335
Phe His Gly Gln Ile Met Gln Leu Asp Ala Ser Pro Val Pro Leu Ala
340 345 350
Glu Asp Asp Pro Val Val Pro Gly Ser Ile Val Gly Leu Gly Leu Phe
355 360 365
Cys Ala Lys Asp Leu Gln Arg Glu Asp Arg Val Ala Phe Asp Asp Gly
370 375 380
Ala Arg Asp Ser Tyr Gly Met Pro Ala Met Arg Ile His Tyr Arg Leu
385 390 395 400
Thr Glu Arg Asp Arg Glu Val Leu Glu Arg Ala Arg Gln Glu Ile Val
405 410 415
Arg Leu Gly Lys Ala Val Gly Glu Pro Leu Asp Glu Gln Pro Phe Val
420 425 430
Leu Pro Pro Gly Ala Ser Leu His Tyr Gln Gly Thr Thr Arg Met Ala
435 440 445
Arg Thr Asp Asp Gly Glu Ser Val Cys Ser Pro Asp Ser Glu Val Trp
450 455 460
Gln Val Pro Gly Leu Phe Val Ala Gly Asn Gly Val Ile Pro Thr Ala
465 470 475 480
Thr Ala Cys Asn Pro Thr Leu Thr Ala Val Ala Leu Ala Val Arg Gly
485 490 495
Ala Arg Lys Val Ala Glu Lys Leu Asn Ser Ser Leu Leu Met Ser Asn
500 505 510
Ser Asp Asn Arg Val Ser Lys Gly Gly Ser Gly Ser Gly His His His
515 520 525
His His His
530
<210> 8
<211> 653
<212> PRT
<213> 白囊耙齿菌(Irpex lacteus)
<400> 8
Met Ser Asn Leu Pro Pro His Glu Ile His Ala Lys Thr Gly Ile Asn
1 5 10 15
Gln Phe Asp Val Phe Ile Ala Gly Ser Gly Pro Ile Gly Ala Thr Tyr
20 25 30
Ala Arg Leu Leu Thr Arg His Gly Tyr Asn Val Ile Met Thr Glu Ile
35 40 45
Gly Asp Gln Glu Thr Arg Val Pro Ala Ser His Lys Lys Asn Glu Ile
50 55 60
Glu Tyr Gln Lys Asp Ile Asp Arg Phe Val Arg Val Ile Gln Gly Ala
65 70 75 80
Leu Ser Thr Val Ser Val Pro Pro Ala Ser Thr Val Ile Pro Gln Leu
85 90 95
Asp Pro Ser Ala Trp Arg Pro Glu Asp Pro Ser Gln Met Thr Leu Leu
100 105 110
Asn Gly Arg Asn Pro Asn Gln Gln Thr Tyr Asp Asn Leu Pro Ala Glu
115 120 125
Ser Val Thr Arg Cys Val Gly Gly Met Ser Thr His Trp Thr Cys Ala
130 135 140
Thr Pro Glu Phe Phe Lys Glu Asn Gly Glu Arg Pro Lys Ile Phe Pro
145 150 155 160
Gly Asp Glu Thr Leu Asp Asp Asp Glu Trp Lys Leu Leu Tyr Glu Ala
165 170 175
Ala Arg Asn Leu Ile Gly Val Ser Ser Thr Glu Phe Asp Gln Ser Ile
180 185 190
Arg His Asn Thr Val Leu His Thr Leu Gln Lys Ala Phe Pro Asn Arg
195 200 205
Gly Ile Lys Pro Leu Pro Leu Ala Cys His Arg Leu Ala Lys Gly Ser
210 215 220
Pro Tyr Val Arg Trp His Ala Ala Asp Asn Val Tyr Tyr Asp Leu Phe
225 230 235 240
Asp Gln Ser Leu Phe Gly Lys Val Asn Ser Glu Gly Ile Ala Arg Gly
245 250 255
Lys Phe Phe Leu Leu Thr Asn Thr Arg Cys Thr Lys Leu His Thr Ser
260 265 270
Asn Pro Asn Ala Thr Lys Asp Val Asn Val Gly Val Ala Glu Val Met
275 280 285
Asp Leu Leu Ala Asp Arg Phe Thr Gly Ser Asp Gln His Lys Gln Val
290 295 300
Ser Phe Ala Ile Asn Ala Lys Val Tyr Val Val Ala Ala Gly Ala Val
305 310 315 320
Ala Thr Pro Gln Ile Leu Ala Asn Ser Asp Phe Gly Gly Leu Glu Gly
325 330 335
Gln Gln Gly Lys Ala Leu Leu Pro Ala Leu Gly Val Gly Ile Thr Glu
340 345 350
Gln Pro Leu Ala Phe Cys Gln Ile Ile Leu Asn Gln His Ile Val Asp
355 360 365
Asp Leu Lys Asn Leu Asn Gly Arg Pro Gln Trp Trp Lys Asp Ala Val
370 375 380
Glu Ala His Arg Arg Ala His Pro Lys Asp Pro Leu Trp Ile Pro Phe
385 390 395 400
Gln Asp Pro Glu Pro Gln Val Asn Ile Pro Val Thr Lys Asp Phe Pro
405 410 415
Trp His Ala Gln Ile His Arg Asp Ala Phe Ser Tyr Gly Glu Ala Gly
420 425 430
Pro Arg Ala Asp Ser Arg Val Val Val Asp Leu Arg Phe Phe Ala Arg
435 440 445
Gln Ala Arg Glu Pro Lys Asn Lys Leu Thr Phe Asp Lys Lys Ile Thr
450 455 460
Asp Val Tyr Gly Met Pro Gln Pro Thr Phe Lys Tyr Leu Pro Thr Thr
465 470 475 480
Gln Tyr Ala Asp Glu Ala Gly Lys Met Met Lys Asp Met Thr Glu Val
485 490 495
Ala Ser Ala Leu Gly Gly Tyr Leu Pro Gly Ser Glu Pro Gln Phe Met
500 505 510
Ala Pro Gly Leu Ala Leu His Leu Gly Gly Thr Val Arg Leu Gly His
515 520 525
Gly Ser Glu Ile Asn Glu Ser Val Ala Asn Phe Asn Ser Gln Val Trp
530 535 540
Asn Phe Lys Asn Leu Tyr Val Ala Gly Asn Gly Thr Ile Pro Thr Ala
545 550 555 560
Phe Ala Ala Asn Pro Thr Leu Thr Ser Ile Ala Leu Ala Leu Arg Ala
565 570 575
Thr His His Ile Val Lys Val Leu Lys Ala Asp Pro Asn Asn Leu Lys
580 585 590
Pro Ala Val Pro Glu Glu Lys Leu Glu Ala Thr Pro Lys Glu Tyr Leu
595 600 605
Lys Trp Leu Thr Asp Pro Thr Asn Pro Asp Phe Pro Asp His His Asp
610 615 620
Leu Gln Lys Glu His Lys Glu Val Ile Val Lys Ala Glu Pro Ser His
625 630 635 640
Thr Gly Gly Ser Gly Ser Gly His His His His His His
645 650
<210> 9
<211> 633
<212> PRT
<213> 黄孢原毛平革菌(Phanerochaete chrysosporium)
<400> 9
Met Phe Leu Asp Thr Thr Pro Phe Arg Ala Asp Glu Pro Tyr Asp Val
1 5 10 15
Phe Ile Ala Gly Ser Gly Pro Ile Gly Ala Thr Phe Ala Lys Leu Cys
20 25 30
Val Asp Ala Asn Leu Arg Val Cys Met Val Glu Ile Gly Ala Ala Asp
35 40 45
Ser Phe Thr Ser Lys Pro Met Lys Gly Asp Pro Asn Ala Pro Arg Ser
50 55 60
Val Gln Phe Gly Pro Gly Gln Val Pro Ile Pro Gly Tyr His Lys Lys
65 70 75 80
Asn Glu Ile Glu Tyr Gln Lys Asp Ile Asp Arg Phe Val Asn Val Ile
85 90 95
Lys Gly Ala Leu Ser Thr Cys Ser Ile Pro Thr Ser Asn Asn His Ile
100 105 110
Ala Thr Leu Asp Pro Ser Val Val Ser Asn Ser Leu Asp Lys Pro Phe
115 120 125
Ile Ser Leu Gly Lys Asn Pro Ala Gln Asn Pro Phe Val Asn Leu Gly
130 135 140
Ala Glu Ala Val Thr Arg Gly Val Gly Gly Met Ser Thr His Trp Thr
145 150 155 160
Cys Ala Thr Pro Glu Phe Phe Ala Pro Ala Asp Phe Asn Ala Pro His
165 170 175
Arg Glu Arg Pro Lys Leu Ser Thr Asp Ala Ala Glu Asp Ala Arg Ile
180 185 190
Trp Lys Asp Leu Tyr Ala Gln Ala Lys Glu Ile Ile Gly Thr Ser Thr
195 200 205
Thr Glu Phe Asp His Ser Ile Arg His Asn Leu Val Leu Arg Lys Tyr
210 215 220
Asn Asp Ile Phe Gln Lys Glu Asn Val Ile Arg Glu Phe Ser Pro Leu
225 230 235 240
Pro Leu Ala Cys His Arg Leu Thr Asp Pro Asp Tyr Val Glu Trp His
245 250 255
Ala Thr Asp Arg Ile Leu Glu Glu Leu Phe Thr Asp Pro Val Lys Arg
260 265 270
Gly Arg Phe Thr Leu Leu Thr Asn His Arg Cys Thr Lys Leu Val Phe
275 280 285
Lys His Tyr Arg Pro Gly Glu Glu Asn Glu Val Asp Tyr Ala Leu Val
290 295 300
Glu Asp Leu Leu Pro His Met Gln Asn Pro Gly Asn Pro Ala Ser Val
305 310 315 320
Lys Lys Ile Tyr Ala Arg Ser Tyr Val Val Ala Cys Gly Ala Val Ala
325 330 335
Thr Ala Gln Val Leu Ala Asn Ser His Ile Pro Pro Asp Asp Val Val
340 345 350
Ile Pro Phe Pro Gly Gly Glu Lys Gly Ser Gly Gly Gly Glu Arg Asp
355 360 365
Ala Thr Ile Pro Thr Pro Leu Met Pro Met Leu Gly Lys Tyr Ile Thr
370 375 380
Glu Gln Pro Met Thr Phe Cys Gln Val Val Leu Asp Ser Ser Leu Met
385 390 395 400
Glu Val Val Arg Asn Pro Pro Trp Pro Gly Leu Asp Trp Trp Lys Glu
405 410 415
Lys Val Ala Arg His Val Glu Ala Phe Pro Asn Asp Pro Ile Pro Ile
420 425 430
Pro Phe Arg Asp Pro Glu Pro Gln Val Thr Ile Lys Phe Thr Glu Glu
435 440 445
His Pro Trp His Val Gln Ile His Arg Asp Ala Phe Ser Tyr Gly Ala
450 455 460
Val Ala Glu Asn Met Asp Thr Arg Val Ile Val Asp Tyr Arg Phe Phe
465 470 475 480
Gly Tyr Thr Glu Pro Gln Glu Ala Asn Glu Leu Val Phe Gln Gln His
485 490 495
Tyr Arg Asp Ala Tyr Asp Met Pro Gln Pro Thr Phe Lys Phe Thr Met
500 505 510
Ser Gln Asp Asp Arg Ala Arg Ala Arg Arg Met Met Asp Asp Met Cys
515 520 525
Asn Ile Ala Leu Lys Ile Gly Gly Tyr Leu Pro Gly Ser Glu Pro Gln
530 535 540
Phe Met Thr Pro Gly Leu Ala Leu His Leu Ala Gly Thr Thr Arg Cys
545 550 555 560
Gly Leu Asp Thr Gln Lys Thr Val Gly Asn Thr His Cys Lys Val His
565 570 575
Asn Phe Asn Asn Leu Tyr Val Gly Gly Asn Gly Val Ile Glu Thr Gly
580 585 590
Phe Ala Ala Asn Pro Thr Leu Thr Ser Ile Cys Tyr Ala Ile Arg Ala
595 600 605
Ser Asn Asp Ile Ile Ala Lys Phe Gly Arg His Arg Gly Gly Gly Ser
610 615 620
Gly Ser Gly His His His His His His
625 630
<210> 10
<211> 613
<212> PRT
<213> 构巢曲霉(Aspergillus nidulans)
<400> 10
Met Gln Tyr Ser Arg Met Thr Ala Thr Arg Glu Asn Pro Lys Tyr Lys
1 5 10 15
Asn Leu Arg Val Glu Glu Cys Asp Val Leu Ile Ile Gly Ser Gly Pro
20 25 30
Val Gly Ala Thr Tyr Ala Arg Glu Ile Leu Asp Pro Gly Ser Gly Ala
35 40 45
Ser Pro Gly Arg Lys Ala Pro Lys Val Ile Met Val Glu Thr Gly Ala
50 55 60
Gln Glu Ser Lys Val Pro Gly Glu His Lys Lys Asn Ala Val Val Tyr
65 70 75 80
Gln Lys His Ile Asp Ser Phe Val Asn Val Ile Gln Gly Ser Leu Phe
85 90 95
Ala Thr Ser Val Pro Thr Arg Val Asp Pro Asn Leu Lys Leu Pro Pro
100 105 110
Val Ser Trp Ser Pro Arg Glu Lys Gln Asn Phe Asn Gly Gln Asn Lys
115 120 125
Glu Gln Asn Ile Tyr His Asn Leu Asp Ala Asn Gly Val Ser Arg Asn
130 135 140
Val Gly Gly Met Ser Thr His Trp Thr Cys Ala Thr Pro Arg Gln His
145 150 155 160
Glu Leu Glu Arg Ser Lys Ile Phe Asp Asp Ala Thr Trp Asp Arg Leu
165 170 175
Tyr Lys Arg Ala Glu Glu Leu Ile Gly Thr Arg Thr Asp Val Leu Asp
180 185 190
Gln Ser Ile Arg Gln Arg Leu Val Leu Asp Ile Leu Arg Lys Lys Phe
195 200 205
Lys Asn Arg Asp Ala Lys Ala Leu Pro Leu Ala Ala Glu Lys Val Glu
210 215 220
Gly Lys Asn Leu Ile Lys Trp Ser Ser Ser Ser Thr Val Leu Gly Asn
225 230 235 240
Leu Leu Glu Asp Glu Lys Phe Thr Leu Leu Asp Gln His His Cys Glu
245 250 255
Lys Leu Glu Phe Asn Asp Glu Thr Asn Lys Val Ser Phe Ala Ile Ile
260 265 270
Lys Asn Leu Ala Lys Pro Gln Thr Ser Lys Glu Asp Glu Asp Arg Leu
275 280 285
Arg Ile Lys Ala Lys Tyr Val Ile Val Cys Gly Gly Pro Ile Leu Thr
290 295 300
Pro Gln Leu Leu Phe Lys Ser Gly Phe Arg Tyr Asp Glu Glu Asp Ala
305 310 315 320
Glu Asp Ser Glu Gly Asn Lys Ser Ser Leu Tyr Ile Pro Ala Leu Gly
325 330 335
Arg Asn Leu Thr Glu Gln Thr Met Cys Phe Cys Gln Ile Val Leu Lys
340 345 350
Asp Lys Trp Val Glu Glu Leu Gln Lys Asn Asn Trp Gly Pro Glu Cys
355 360 365
Glu Glu His Arg Arg Lys Tyr Asp Glu Glu Asp Asp Pro Leu Arg Ile
370 375 380
Pro Phe Asp Asp Leu Asp Pro Gln Val Thr Leu Pro Phe Thr Glu Asn
385 390 395 400
Thr Pro Trp His Thr Gln Ile His Arg Asp Ala Phe Ser Tyr Gly Ala
405 410 415
Val Pro Pro Ala Ile Asp Lys Arg Thr Ile Val Asp Leu Arg Tyr Phe
420 425 430
Gly Arg Ala Glu Thr Gln Trp Arg Asn Arg Val Thr Phe Ser Lys Lys
435 440 445
Leu Thr Asp Ala Tyr Gly Met Pro Gln Pro Thr Phe Asp Phe Lys Leu
450 455 460
Ser Thr Lys Asp Arg Leu Glu Ser His Arg Met Met Gln Asp Met Glu
465 470 475 480
Lys Val Ala Gly Glu Leu Gly Gly Tyr Leu Pro Gly Ser Glu Pro Gln
485 490 495
Phe Leu Ala Pro Gly Leu Ala Leu His Val Cys Gly Thr Thr Ala Ala
500 505 510
Leu Arg Lys Gly Cys Arg Ser Glu Asp Glu Met Lys Arg Ile Ser Val
515 520 525
Cys Asp Glu Asn Ser Lys Val Trp Gly Val Glu Asn Leu His Leu Gly
530 535 540
Gly Leu Asn Val Ile Pro Gly Pro Arg Ser Asn Ala Ser Asn Pro Thr
545 550 555 560
Leu Thr Ala Met Cys Phe Ala Ile Lys Gly Ala Glu Glu Ile Arg Arg
565 570 575
Lys Leu Gly Lys Lys Gly Ser His Ser Gly Asn Arg Asp Asp Gly Asp
580 585 590
Val Asp Thr Asp Thr Asp Asp Asp Ala Gly Gly Ser Gly Ser Gly His
595 600 605
His His His His His
610
<210> 11
<211> 635
<212> PRT
<213> 多色栓菌(Trametes multicolor)
<400> 11
Met Ser Thr Ser Ser Ser Asp Pro Phe Phe Asn Phe Ala Lys Ser Ser
1 5 10 15
Phe Arg Ser Ala Ala Ala Gln Lys Ala Ser Ala Ser Ser Leu Pro Pro
20 25 30
Leu Pro Gly Pro Asp Lys Lys Val Pro Gly Met Asp Ile Lys Tyr Asp
35 40 45
Val Val Ile Val Gly Ser Gly Pro Ile Gly Cys Thr Tyr Ala Arg Glu
50 55 60
Leu Val Gly Ala Gly Tyr Lys Val Ala Met Phe Asp Ile Gly Glu Ile
65 70 75 80
Asp Ser Gly Leu Lys Ile Gly Ala His Lys Lys Asn Thr Val Glu Tyr
85 90 95
Gln Lys Asn Ile Asp Lys Phe Val Asn Val Ile Gln Gly Gln Leu Met
100 105 110
Ser Val Ser Val Pro Val Asn Thr Leu Val Val Asp Thr Leu Ser Pro
115 120 125
Thr Ser Trp Gln Ala Ser Thr Phe Phe Val Arg Asn Gly Ser Asn Pro
130 135 140
Glu Gln Asp Pro Leu Arg Asn Leu Ser Gly Gln Ala Val Thr Arg Val
145 150 155 160
Val Gly Gly Met Ser Thr His Trp Thr Cys Ala Thr Pro Arg Phe Asp
165 170 175
Arg Glu Gln Arg Pro Leu Leu Val Lys Asp Asp Ala Asp Ala Asp Asp
180 185 190
Ala Glu Trp Asp Arg Leu Tyr Thr Lys Ala Glu Ser Tyr Phe Gln Thr
195 200 205
Gly Thr Asp Gln Phe Lys Glu Ser Ile Arg His Asn Leu Val Leu Asn
210 215 220
Lys Leu Thr Glu Glu Tyr Lys Gly Gln Arg Asp Phe Gln Gln Ile Pro
225 230 235 240
Leu Ala Ala Thr Arg Arg Ser Pro Thr Phe Val Glu Trp Ser Ser Ala
245 250 255
Asn Thr Val Phe Asp Leu Gln Asn Arg Pro Asn Thr Asp Ala Pro Glu
260 265 270
Glu Arg Phe Asn Leu Phe Pro Ala Val Ala Cys Glu Arg Val Val Arg
275 280 285
Asn Ala Leu Asn Ser Glu Ile Glu Ser Leu His Ile His Asp Leu Ile
290 295 300
Ser Gly Asp Arg Phe Glu Ile Lys Ala Asp Val Tyr Val Leu Thr Ala
305 310 315 320
Gly Ala Val His Asn Thr Gln Leu Leu Val Asn Ser Gly Phe Gly Gln
325 330 335
Leu Gly Arg Pro Asn Pro Ala Asn Pro Pro Glu Leu Leu Pro Ser Leu
340 345 350
Gly Ser Tyr Ile Thr Glu Gln Ser Leu Val Phe Cys Gln Thr Val Met
355 360 365
Ser Thr Glu Leu Ile Asp Ser Val Lys Ser Asp Met Thr Ile Arg Gly
370 375 380
Thr Pro Gly Glu Leu Thr Tyr Ser Val Thr Tyr Thr Pro Gly Ala Ser
385 390 395 400
Thr Asn Lys His Pro Asp Trp Trp Asn Glu Lys Val Lys Asn His Met
405 410 415
Met Gln His Gln Glu Asp Pro Leu Pro Ile Pro Phe Glu Asp Pro Glu
420 425 430
Pro Gln Val Thr Thr Leu Phe Gln Pro Ser His Pro Trp His Thr Gln
435 440 445
Ile His Arg Asp Ala Phe Ser Tyr Gly Ala Val Gln Gln Ser Ile Asp
450 455 460
Ser Arg Leu Ile Val Asp Trp Arg Phe Phe Gly Arg Thr Glu Pro Lys
465 470 475 480
Glu Glu Asn Lys Leu Trp Phe Ser Asp Lys Ile Thr Asp Ala Tyr Asn
485 490 495
Met Pro Gln Pro Thr Phe Asp Phe Arg Phe Pro Ala Gly Arg Thr Ser
500 505 510
Lys Glu Ala Glu Asp Met Met Thr Asp Met Cys Val Met Ser Ala Lys
515 520 525
Ile Gly Gly Phe Leu Pro Gly Ser Leu Pro Gln Phe Met Glu Pro Gly
530 535 540
Leu Val Leu His Leu Gly Gly Thr His Arg Met Gly Phe Asp Glu Lys
545 550 555 560
Glu Asp Asn Cys Cys Val Asn Thr Asp Ser Arg Val Phe Gly Phe Lys
565 570 575
Asn Leu Phe Leu Gly Gly Cys Gly Asn Ile Pro Thr Ala Tyr Gly Ala
580 585 590
Asn Pro Thr Leu Thr Ala Met Ser Leu Ala Ile Lys Ser Cys Glu Tyr
595 600 605
Ile Lys Gln Asn Phe Thr Pro Ser Pro Phe Thr Ser Glu Ala Gln Gly
610 615 620
Gly Ser Gly Ser Gly His His His His His His
625 630 635
Claims (25)
1.一种用于制备2,5-呋喃二甲酸的化学酶方法,所述方法包括:
将D-葡萄糖与(i)选自基本上由半乳糖氧化酶、吡喃糖2-氧化酶、葡糖二酸脱水酶、过氧化氢酶组成的组的至少两种酶及其组合接触,以产生中间体;和(ii)将所述中间体与金属催化剂和酸催化剂接触,以形成2,5-呋喃二甲酸。
2.根据权利要求1所述的化学酶方法,其中将D-葡萄糖与半乳糖氧化酶和过氧化氢酶接触以形成D-己二醛葡糖;并且其中所述方法还包括:
将D-己二醛葡糖与吡喃糖-2-氧化酶和过氧化氢酶在适合于形成2-酮基-己二醛葡糖的条件下接触;
将2-酮基-己二醛葡糖与非均相金属催化剂接触,以形成2-酮基-葡糖二酸;
将2-酮基葡糖二酸在酸催化剂存在下脱水,以形成2,5-呋喃二甲酸。
3.根据权利要求1所述的化学酶方法,其中将D-葡萄糖与半乳糖氧化酶和过氧化氢酶接触以形成D-己二醛葡糖;并且其中所述方法还包括:
将D-己二醛葡糖与吡喃糖-2-氧化酶和过氧化氢酶在适合于形成2-酮基-己二醛葡糖的条件下接触;
将2-酮基-己二醛葡糖用酸催化剂脱水,以形成2,5-呋喃二甲醛;和
将2,5-呋喃二甲醛在非均相金属催化剂存在下氧化,以形成2,5-呋喃二甲酸。
4.根据权利要求1所述的化学酶方法,其中将D-葡萄糖与半乳糖氧化酶和过氧化氢酶接触以形成D-己二醛葡糖;并且其中所述方法还包括:
将D-己二醛葡糖与金属催化剂接触,以形成D-葡糖二酸;
将D-葡糖二酸用葡糖二酸脱水酶脱水,以形成5-酮基-4-脱氧己二醛葡糖;和
将5-酮基-4-脱氧己二醛葡糖在酸催化剂存在下环化,以形成2,5-呋喃二甲酸。
5.根据权利要求1所述的化学酶方法,其中将D-葡萄糖与吡喃糖-2-氧化酶和过氧化氢酶接触以形成2-酮基-葡萄糖;并且其中所述方法还包括:
将2-酮基-葡萄糖用酸催化剂在适合于形成2,5-呋喃二甲醛的条件下脱水;
将5-酮基-4-脱氧己二醛葡糖用酸催化剂脱水,以形成2,5-呋喃二甲醛;和
将2,5-呋喃二甲醛在非均相金属催化剂存在下氧化,以形成2,5-呋喃二甲酸。
6.根据权利要求1所述的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1至SEQID NO.:6中的任一者。
7.根据权利要求2所述的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1至SEQID NO.:6中的任一者。
8.根据权利要求3所述的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1至SEQID NO.:6中的任一者。
9.根据权利要求4所述的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1至SEQID NO.:6中的任一者。
10.根据权利要求5所述的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1至SEQ ID NO.:6中的任一者。
11.根据权利要求1所述的化学酶方法,其中所述半乳糖氧化酶具有SEQ ID NO.:1。
12.根据权利要求1所述的化学酶方法,其中所述丙酮酸-2-氧化酶具有SEQ ID NO.:7至SEQ ID NO.:11中的任一者。
13.根据权利要求1所述的化学酶方法,其在低于约100℃的温度下进行。
14.根据权利要求1所述的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
15.根据权利要求2所述的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
16.根据权利要求3所述的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
17.根据权利要求4所述的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
18.根据权利要求5所述的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
19.根据权利要求1所述的化学酶方法,其中所述非均相金属催化剂含有包含碳、二氧化硅、氧化铝、二氧化钛(TiO2)、氧化锆(ZrO2)、沸石或其任何组合的支撑体。
20.根据权利要求1所述的化学酶方法,其中所述酸催化剂、金属催化剂或两者是非均相的。
21.根据权利要求1所述的化学酶方法,其中所述酸催化剂、金属催化剂或两者是均相的。
22.根据权利要求1所述的化学酶方法,其还包括对所述2,5-呋喃二甲酸进行水结晶、溶剂结晶和Nutsche过滤。
23.一种用于制备2,5-呋喃二甲酸的化学酶方法,所述方法包括:
使用酶氧化组合物对5-羟甲基糠醛进行酶氧化以形成中间体,所述组合物包含选自芳基醇氧化酶(AAO)、氯过氧化物酶(CPO)、5-羟甲基糠醛氧化酶(HMFO)、乙二醛氧化酶(GLOX)、周质醛氧化酶(PaoABC)、非特异性过氧化酶(UPO)、辣根过氧化物酶(HRP)、伴有或不伴有激活酶辣根过氧化物酶(HRP)的半乳糖氧化酶(GAO)、乳过氧化物酶(LPO)、髓过氧化物酶(MPO)、嗜酸性粒细胞过氧化物酶(EPO)、甲状腺过氧化物酶(TPO)、卵过氧化物酶、唾液过氧化物酶、钒卤过氧化物酶、非哺乳动物脊椎动物过氧化物酶(POX)、过氧蛋白(Pxd)、细菌过氧素(Pxc)、无脊椎动物过氧连接蛋白(Pxt)和短过氧对接蛋白(PxDo)、短过氧对接蛋白(Pxt)、α-加双氧酶(aDox)、双重氧化酶(DuOx)、***素H合酶或环加氧酶(PGHS/CyOx)、亚油酸二醇合酶(LDS)、其功能性变体的一种或多种酶及其任何组合;和
使用金属催化剂氧化所述中间体,以形成2,5-呋喃二甲酸。
24.根据权利要求23所述的化学酶方法,其中所述酶氧化在低于约100℃的温度下进行。
25.根据权利要求23所述的化学酶方法,其中所述2,5-呋喃二甲酸具有高于约80%的纯度。
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