CN112662656B - 酶固定化载体及其制备方法、固定化酶及其制备方法 - Google Patents
酶固定化载体及其制备方法、固定化酶及其制备方法 Download PDFInfo
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- CN112662656B CN112662656B CN202110288881.1A CN202110288881A CN112662656B CN 112662656 B CN112662656 B CN 112662656B CN 202110288881 A CN202110288881 A CN 202110288881A CN 112662656 B CN112662656 B CN 112662656B
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- 108010027345 wheylin-1 peptide Proteins 0.000 description 1
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Abstract
本发明提供了一种酶固定化载体及其制备方法、固定化酶及其制备方法。上述酶固定化载体为超交联聚乙烯醇经氨基修饰或三聚氯氰修饰得到。利用本发明提供的酶固定化载体,能够有效提高固定化酶的稳定性和重复使用性。而且,由于采用了酶共价连接的形式,相较于包埋法,无需进行化学试剂浸泡等,有利于保持酶自身活性,促使固定化酶在稳定、可重复使用的同时兼具更好的活性。
Description
技术领域
本发明涉及生物催化技术领域,具体而言,涉及一种酶固定化载体及其制备方法、固定化酶及其制备方法。
背景技术
相较于化学催化剂,生物催化剂—酶因其高活性、选择性和底物的专一性好而被广泛应用于工业生产过程中。生物催化正在成为化学品、中间体、精细化学品和最终药物分子制造计划的重要组成部分。虽然酶具有高的区域选择性、高的催化效率和温和的反应条件,但由于游离酶的催化活性受到温度、pH值、溶剂等因素影响,很容易失活。随着工艺需求的不断扩大,对酶应用的效率和经济性的要求也就越来越高。因此,这不仅需要增强酶活性、特异性和生产力,还需要提高酶的可回收性和重复利用性。
通过将酶固定到固体载体上来实现固定化,由此获得非均相固定化酶系统为上述问题提供了一个很好的解决方案。固定化酶在保持了酶特有的催化性能的同时,还呈现出稳定性高、分离回收容易、可重复操作使用、工艺简便等一系列优点。固定化酶的性能主要取决于固定化方法和所用的载体材料。按照酶与载体不同的结合方式,目前酶的固定方法可以分为吸附法、共价结合法、交联法以及包埋法等。其中吸附法是酶与载体通物理吸附作用、范德华力、疏水作用等结合,因操作简单方便、吸附容量大、工业成本低等优点,是固定化酶最常用的方法。但是由于载体和酶之间是用过物理吸附作用结合,结合力较弱,所以该种方法存在酶重复使用过程中易从载体上脱落的问题,从而会导致转化率下降。共价结合法是将酶和载体通过共价键连接起来,要求载体上必须带有相应的可以和酶反应生成共价键的官能团。相较于吸附法,酶与载体的连接更加牢固,不会存在使用过程中酶掉落的问题,稳定性和循环性更好。
聚乙烯醇(PVA)是一种高分子有机化合物,对人体无毒、无副作用,具有良好的生物相容性。聚乙烯醇在医疗领域具有广泛使用,可以制成水凝胶,制造软性接触眼镜;可以制成口腔膜,贴于患处,治疗细菌感染;还可以制成医用海绵,用于手术中吸液、吸血。聚乙烯醇可通过石油乙烯法、天然气乙炔法和电石乙炔法等成熟方法进行,生产方便,易于获取,价格低廉。另外聚乙烯醇不同于其它乙烯基聚合物(比如聚苯乙烯),其可被细菌作为碳源利用,可降解,是一种环境友好的材料。
近年来国内外对PVA 载体固定生物活性物质进行了大量的研究,其制备方法主要有PVA-硼酸法和冷冻解冻法。硼酸法包埋生物活性物质机械强度高,使用寿命长,弹性好。缺点是硼酸对被包埋的生物(酶)有毒害作用,生物残余活性低,且固定化颗粒易发生粘联现象。冷冻解冻法应用物理交联形成凝胶,这种方法制得的凝胶含水率较大,但是载体的稳定性不如化学交联法得到的凝胶,很难达到一些生物反应器尤其是流动床反应器的要求。另外,作为固定化载体,除了无毒性和稳定性外,其传质性、负载性也很重要,然而目前固定化微生物研究中的包埋法势必要将固定后的微生物浸泡于化学试剂中或者冷冻而影响微生物的活性及应用效率,而且包埋载体的空隙度小,传质性和负载性受到限制。
因此,如何通过PVA更有效地固定酶,促使固定化酶兼具较高活性和更好的稳定性、可重复性,是本领域亟需解决的问题。
发明内容
本发明的主要目的在于提供一种酶固定化载体及其制备方法、固定化酶及其制备方法,以解决现有技术中聚乙烯醇固定化酶无法兼具较高活性和较好稳定性、可重复性的问题。
为了实现上述目的,根据本发明的一个方面,提供了一种酶固定化载体,其为超交联聚乙烯醇经氨基修饰或三聚氯氰修饰得到。
进一步地,超交联聚乙烯醇为聚乙烯醇依次经氧化、自交联、交联剂交联得到。
进一步地,氨基修饰采用3-氨丙基三乙氧基硅烷为氨基修饰试剂。
根据本发明的另一方面,还提供了一种固定化酶,其由上述酶固定化载体和酶经共价连接形成。
进一步地,酶选自转氨酶、单加氧酶、酮还原酶、烯还原酶、氨基酸脱氢酶中的任意一种或多种;优选地,转氨酶为来源于Chromobacterium violaceum DSM30191的转氨酶或者来源于Arthrobacter citreus的转氨酶,或来源于B.thuringiensis的转氨酶;优选地,单加氧酶为来源于Brachymonas petroleovorans的环己酮单加氧酶,或者来源于Rhodococcus ruber-SD1的环己酮单加氧酶;优选地,酮还原酶为来源于Acetobacter sp. CCTCC M209061的酮还原酶,或者来源于Candida macedoniensis AKU4588的酮还原酶;优选地,烯还原酶为来源于Saccharomyces cerevisiae的烯还原酶和来源于Chryseobacterium sp. CA49的烯还原酶;优选地,氨基酸脱氢酶为来源于Bacillus cereus的亮氨酸脱氢酶和来源于Bacillus sphaericus的苯丙氨酸脱氢酶。
根据本发明的另一方面,还提供了一种上述酶固定化载体的制备方法,其包括以下步骤:提供超交联聚乙烯醇;将超交联聚乙烯醇进行氨基修饰或三聚氯氰修饰,得到酶固定化载体。
进一步地,超交联聚乙烯醇由以下方法制备得到:氧化步骤:将聚乙烯醇溶解于水中,其次加入氧化剂进行氧化反应,得到氧化产物体系;优选地,氧化剂为高碘酸钠;优选地,氧化反应的温度为20~30℃;自交联步骤:用盐酸调节氧化产物体系的氯化氢浓度在0.1~1 mol/L,然后在70~90℃温度下进行自交联反应,得到聚乙烯醇凝胶颗粒;交联剂交联步骤:将聚乙烯凝胶颗粒分散在水中,其次加入交联剂进行反应,得到超交联聚乙烯醇;优选地,交联剂为浓度为2~10wt%的戊二醛溶液;优选地,交联剂交联步骤的反应温度为40~60℃,且期间加入盐酸使体系中氯化氢浓度在0.1~1 mol/L。
进一步地,将超交联聚乙烯醇进行氨基修饰的步骤包括:将超交联聚乙烯醇、第一溶剂、氨基修饰试剂混合并进行反应,得到酶固定化载体;优选地,氨基修饰试剂为3-氨丙基三乙氧基硅烷;优选地,氨基修饰的反应过程中,相对于每克超交联聚乙烯醇,氨基修饰试剂的加入量为0.3~1 mL;优选地,氨基修饰的反应过程中,反应pH值为2~3,反应温度为60~90℃;优选地,第一溶剂为水。
进一步地,将超交联聚乙烯醇进行三聚氯氰修饰的步骤包括:将超交联聚乙烯醇分散于第二溶剂,其次加入三聚氯氰进行反应,得到酶固定化载体;优选地,相对于每克超交联聚乙烯醇,三聚氯氰的加入量为0.25~1g;优选地,三聚氯氰修饰的反应过程中,反应温度为0~10℃;优选地,第二溶剂为丙酮。
根据本发明的另一方面,又提供了一种固定化酶的制备方法,其包括以下步骤:将上述酶固定化载体和酶进行共价连接,得到固定化酶。
进一步地,当酶固定化载体为超交联聚乙烯醇经氨基修饰得到时,固定化酶的制备方法包括以下步骤:将酶固定化载体分散于戊二醛溶液中进行活化,得到活化载体;将活化载体与含酶的酶液进行反应,以使酶与酶固定化载体共价连接,得到固定化酶;优选地,戊二醛溶液为质量浓度为1~2%;更优选地,戊二醛溶液为戊二和磷酸盐缓冲液的混合溶液;优选地,活化步骤中,活化温度为20~30℃,活化时间为1~3 h;优选地,活化载体与酶液进行反应的过程中,反应温度为20~30℃;优选地,每克活化载体对应2~6mL酶液,酶液中的蛋白含量为30~40 mg/mL。
进一步地,当酶固定化载体为超交联聚乙烯醇经三聚氯氰修饰得到时,固定化酶的制备方法包括以下步骤:采用磷酸盐缓冲液将酶固定化载体进行润湿;将润湿后的酶固定化载体与含酶的酶液进行反应,以使酶与酶固定化载体共价连接,得到固定化酶;优选地,将润湿后的酶固定化载体与酶液进行反应的过程中,反应温度为20~30℃;优选地,每克酶固定化载体对应2~6mL酶液,酶液中的蛋白含量为30~40 mg/mL。
具体实施方式
需要说明的是,在不冲突的情况下,本申请中的实施例及实施例中的特征可以相互组合。下面将结合实施例来详细说明本发明。
正如背景技术部分所描述的,现有技术中聚乙烯醇固定化酶无法兼具较高活性和较好稳定性、可重复性。
为了解决上述问题,本发明提供了一种酶固定化载体,其为超交联聚乙烯醇经氨基修饰或三聚氯氰修饰得到。将超交联聚乙烯醇进行氨基修饰或三聚氯氰修饰,可以使聚乙烯醇分子链携带氨基或,从而可以利用这些修饰基团与酶进行反应,达到二者共价连接的效果。因此,利用本发明提供的酶固定化载体,能够有效提高固定化酶的稳定性和重复使用性。而且,由于采用了酶共价连接的形式,相较于包埋法,无需进行化学试剂浸泡等,有利于保持酶自身活性,促使固定化酶在稳定、可重复使用的同时兼具更好的活性。
本发明中超交联聚乙烯醇,超交联是指交联度高至聚合物不溶于水、有机溶剂等聚乙烯醇的良溶剂。
在一种优选的实施方式中,超交联聚乙烯醇为聚乙烯醇依次经氧化、自交联、交联剂交联得到。氧化过程中,PVA链段中头头相连的邻二醇结构的碳碳键断裂,形成两个醛基;自交联过程中,氧化得到的醛基会与PVA链上的羟基反应得到相应的缩醛结构(氧化、自交联过程反应如下)。戊二醛交联剂加入后,可以进一步与PVA链上的羟基反应得到超交联的PVA树脂。
出于提高氨基修饰效率的目的,在一种优选的实施方式中,氨基修饰采用3-氨丙基三乙氧基硅烷为氨基修饰试剂。该3-氨丙基三乙氧基硅烷能够与超交联聚乙烯醇分子链上的羟基进行反应,以在分子链上修饰上基团。更重要地是,选用该基团进行氨基修饰,基团尺寸更为适宜,且沿着远离分子主链的方向逐渐由刚性转变为柔性,有利于后续和酶的固定化反应,从而能够更好地固定酶,进一步提高固定化酶的稳定性和可重复利用性,且具有更好的活性。
根据本发明的另一方面,还提供了一种固定化酶,其由上述酶固定化载体和酶经共价连接形成。如前文所述,本发明的酶固定化载体是将超交联聚乙烯醇进行氨基修饰或三聚氯氰修饰形成,这可以使聚乙烯醇分子链携带氨基或,从而可以利用这些修饰基团与酶进行反应,达到二者共价连接的效果。因此,利用该酶固定化载体,能够有效提高固定化酶的稳定性和重复使用性。而且,由于采用了酶共价连接的形式,相较于包埋法,无需进行化学试剂浸泡等,有利于保持酶自身活性,促使固定化酶在稳定、可重复使用的同时兼具更好的活性。
本发明的固定化酶,对酶具有广泛的适用性,比如,酶包括但不限于转氨酶、单加氧酶、酮还原酶、烯还原酶、氨基酸脱氢酶、中的任意一种或多种。其中对以下酶类更为适用,转氨酶为来源于Chromobacterium violaceum DSM30191的转氨酶或者来源于Arthrobacter citreus的转氨酶,或来源于B.thuringiensis的转氨酶;单加氧酶为来源于Brachymonas petroleovorans的环己酮单加氧酶,或者来源于Rhodococcus ruber-SD1的环己酮单加氧酶;酮还原酶为来源于Acetobacter sp. CCTCC M209061的酮还原酶,或者来源于Candida macedoniensis AKU4588的酮还原酶;氨基酸脱氢酶为来源于Bacillus cereus的亮氨酸脱氢酶和来源于Bacillus sphaericus的苯丙氨酸脱氢酶。
根据本发明的另一方面,还提供了一种上述酶固定化载体的制备方法,其包括以下步骤:提供超交联聚乙烯醇;将超交联聚乙烯醇进行氨基修饰或三聚氯氰修饰,得到酶固定化载体。利用该方法制备的酶固定化载体是以超交联聚乙烯醇为载体本体,在其分子链上修饰了氨基或,这些修饰基团能够与酶进行反应从而将其固定,形成固定化酶,因此能够有效提高固定化酶的稳定性和重复使用性。而且,由于采用了酶共价连接的形式,相较于包埋法,无需进行化学试剂浸泡等,有利于保持酶自身活性,促使固定化酶在稳定、可重复使用的同时兼具更好的活性。
在一种优选的实施方式中,超交联聚乙烯醇由以下方法制备得到:氧化步骤:将聚乙烯醇溶解于水中,其次加入氧化剂进行氧化反应,得到氧化产物体系;自交联步骤:用盐酸调节氧化产物体系的氯化氢浓度在0.1~1 mol/L,在70~90℃温度下进行自交联反应,得到聚乙烯醇凝胶颗粒;交联剂交联步骤:将聚乙烯凝胶颗粒分散在水中,其次加入交联剂进行反应,得到超交联聚乙烯醇。氧化过程中,PVA链段中头头相连的邻二醇结构的碳碳键断裂,形成两个醛基。自交联过程中,氧化得到的醛基会与PVA链上的羟基反应得到相应的缩醛结构。戊二醛交联剂加入后,可以进一步与PVA链上的羟基反应得到超交联的PVA树脂。优选地,氧化剂为高碘酸钠。利用高碘酸钠能够使氧化反应更充分。优选地,氧化反应的温度为20~30℃。优选地,交联剂为戊二醛;优选地,交联剂交联步骤的反应温度为40~60℃,且期间加入盐酸使体系中氯化氢浓度在0.1~1 mol/L 。以上交联剂和交联条件能够促使其与PVA链上的羟基更充分反应,形成结构更稳定的超交联态聚乙烯醇。
为了促进聚乙烯醇溶解,实际操作过程中可将聚乙烯醇加入第一溶剂后,在90℃左右搅拌至溶解。氧化过程在室温进行即可,优选反应时间为1~3h。自交联反应过程中,优选反应时间为3~6h。交联剂交联过程中,优选反应时间为5~8h。
在一种优选的实施方式中,将超交联聚乙烯醇进行氨基修饰的步骤包括:将超交联聚乙烯醇、第一溶剂、氨基修饰试剂混合并进行反应,得到酶固定化载体;优选地,氨基修饰试剂为3-氨丙基三乙氧基硅烷。该3-氨丙基三乙氧基硅烷能够与超交联聚乙烯醇分子链上的羟基进行反应,以在分子链上修饰上基团。更重要地是,选用该基团进行氨基修饰,基团尺寸更为适宜,且沿着远离分子主链的方向逐渐由刚性转变为柔性,有利于后续和酶的固定化反应,从而能够更好地固定酶,进一步提高固定化酶的稳定性和可重复利用性,且具有更好的活性。
优选地,氨基修饰的反应过程中,相对于每克超交联聚乙烯醇,氨基修饰试剂的加入量为1~3ml。将氨基修饰试剂的加入量控制在上述范围,能够更充分地与超交联聚乙烯醇分子链上的羟基进行反应,从而在后续固化酶的过程中能够提高酶的负载量及稳定性。
出于进一步提高反应效率的目的,在一种优选的实施方式中,氨基修饰的反应过程中,反应pH值为2~3,反应温度为60~90℃。具体可以采用pH调节剂调节反应体系的pH值,比如可以采用浓盐酸等。优选地,第一溶剂为水。优选地,反应时间为5~24h。
在一种优选的实施方式中,将超交联聚乙烯醇进行三聚氯氰修饰的步骤包括:将超交联聚乙烯醇分散于第二溶剂,其次加入三聚氯氰进行反应,得到酶固定化载体。相较于氨基作为修饰基团,以三聚氯氰进行修饰,后续酶固化过程中无需额外使用戊二醛等交联剂,将酶固化载体与酶液直接反应即可。优选地,相对于每克超交联聚乙烯醇,三聚氯氰的加入量为0.25~1g。将三聚氯氰的用量控制在上述范围内,有利于促使分子链上羟基与三聚氯氰更充分反应,从而提高载体对酶的载量,同时进一步提高固定化酶的稳定性和活性。
为了进一步提高反应稳定性和效率,在一种优选的实施方式中,三聚氯氰修饰的反应过程中,反应温度为0~10℃。优选地,所述第二溶剂为丙酮。优选地,反应时间为2~6h。
根据本发明的又一方面,还提供了一种固定化酶的制备方法,其包括以下步骤:将上述酶固定化载体和酶进行共价连接,得到固定化酶。通过上述载体,可利用氨基和三聚氯氰修饰基团与酶进行反应,从而在二者之间形成共价连接。相较于物理吸附固定,共价连接形成的固定化酶具有更好的稳定性和可重复利用性,相较于包埋法等,利用共价连接促使固定化酶保持较高的酶活性,对于长期稳定保持催化活性具有很好的改善作用。
在一种优选的实施方式中,当酶固定化载体为超交联聚乙烯醇经氨基修饰得到时,固定化酶的制备方法包括以下步骤:将酶固定化载体分散于戊二醛溶液中进行活化,得到活化载体;将活化载体与含酶的酶液进行反应,以使酶与酶固定化载体共价连接,得到固定化酶。经过戊二醛活化,再将活化载体与含酶的酶液进行反应,即可促使修饰氨基与酶完成化学反应,达到酶固定的作用。戊二醛一个醛基和载体上的氨基反应形成亚胺键,另一个醛基和酶上游离的氨基反应,这样就把酶和载体接在一起了。
为使活化更为充分,优选地,戊二醛溶液为质量浓度为1~2%;更优选地,戊二醛溶液为戊二和磷酸盐缓冲液的混合溶液。上述磷酸盐缓冲液优选为pH为7.0的磷酸盐缓冲液(可以为磷酸氢二钠缓冲液或磷酸二氢钠缓冲液)。优选地,活化步骤中,活化温度为20~30℃,活化时间为1~3h。在上述温度下进行戊二醛活化,效果更佳,反应更稳定。优选地,活化载体与酶液进行反应的过程中,反应温度为20~30℃。在上述温度下进行酶的固定反应,具有更好的反应效率和稳定性。优选地,每克活化载体对应2~6mL酶液,酶液中的蛋白含量为30~40 mg/mL。这样,有利于促使酶更充分地固定于载体上,提高酶载量,进而提高固定化酶的活性。优选地,上述活化载体与酶液的反应时间为15~25h。
在一种优选的实施方式中,当酶固定化载体为超交联聚乙烯醇经三聚氯氰修饰得到时,固定化酶的制备方法包括以下步骤:采用磷酸盐缓冲液将酶固定化载体进行润湿;将润湿后的酶固定化载体与含酶的酶液进行反应,以使酶与酶固定化载体共价连接,得到固定化酶。上述磷酸盐缓冲液优选为pH为7.0的磷酸盐缓冲液。经润湿后,载体中的三聚氯氰修饰基团即可与酶液中的酶进行固定化反应,以形成二者之间的共价连接。
为了提高反应过程中的稳定性,同时提高反应效率,在一种优选的实施方式中,将润湿后的酶固定化载体与酶液进行反应的过程中,反应温度为20~30℃。更优选地,每克酶固定化载体对应2~6mL酶液,酶液中的蛋白含量为30~40 mg/mL。这样有利于促使酶更充分地固定,提供载量,并使固定化酶具有更高的催化活性。优选地,上述酶固定化载体与酶液的反应时间为15~25h。
以下结合具体实施例对本申请作进一步详细描述,这些实施例不能理解为限制本申请所要求保护的范围。
以下实施例中采用的酶来源如下表1:
表1
实施例1
固定化载体制备实施例:
PVA氧化:将PVA(10 g)加入到100 mL 纯水中,在90℃下搅拌至完全溶解。之后将其冷却至室温,向其中加入高碘酸钠(0.9 g)搅拌反应1小时。
PVA自交联:用36%的浓盐酸将上一步氧化的PVA溶液调节至的氯化氢浓度在0.1mol/L,之后升温至70℃静置反应3小时,形成PVA凝胶。将得到的自交联PVA凝胶过筛(20目)得到凝胶颗粒(SCL-PVA),并用纯水洗涤三遍。
PVA胶粒进一步交联:将上述得到的SCL-PVA胶粒分散到100 mL纯水中,并向其中加入50wt%戊二醛(20mL)和36%的浓盐酸(25 mL)搅拌均匀后升温至50℃反应6小时。之后用纯水将所得胶粒洗到中性干燥后,得到大孔超交联PVA(MP-PVA)。
实施例2
氨基修饰制备固定化载体实施例:
取MP-PVA 3 g,加入100 mL去离子水及2 mL APTES,室温下搅拌30 min后,用浓盐酸调pH至3.5,搅拌5 min后升温至80℃,N2保护下反应20 h(反应路线如下)。反应结束后依次用乙醇,去离子水清洗,得到氨基修饰固定化载体MP-PVA-NH2。
实施例3
三聚氯氰修饰固定化载体实施例:
1 g烘干的MP-PVA加入40 mL丙酮,在冰水浴(0℃)中搅拌30 min后加入0.5 g三聚氯氰,并继续在冰水浴中反应4 h。反应结束后用丙酮清洗并抽滤至干燥,得到三聚氯氰修饰的酶固定化载体MP-PVA-CC。
实施例4
MP-PVA-NH2酶固定化:
用20 mM pH为7.0的磷酸二氢钠缓冲液配制1wt%戊二醛溶液,称取1 g MP-PVA-NH2分散于上述溶液中。于30 ℃下孵化1 h,随后用去离子水洗涤三次。取一定量配制好的酶液(蛋白含量30~40 mg/mL)加入到戊二醛活化后的MP-PVA-NH2中(4 mL酶液对应1 g 载体),在20 ℃进行固定化20 h,制得MP-PVA-NH2固定化酶。
实施例5
MP-PVA-CC酶固定化:
用20 mM pH为7.0的磷酸二氢钠缓冲液将MP-PVA-CC润湿洗涤3遍。取一定量配制好的酶液(蛋白含量30~40 mg/mL)加入MP-PVA-CC中(4 mL酶液对应1 g 载体),在20 ℃进行固定化20 h,制得MP-PVA-CC固定化酶。
应用实施例1
MP-PVA-NH2和MP-PVA-CC固定转氨酶(TA)活性及重复使用性测试:
酶催化反应路线如下:
在20 mL的反应瓶中,加入0.5 mL 甲醇,溶解0.1 g羰基底物,并加入15 eq 异丙胺盐酸盐和25.0 mg PLP(5’-磷酸吡哆醛),补加0.1 M 磷酸盐缓冲液(PB 8.0)至反应液终体积为5 mL,形成待反应体系;
分别独立地向待反应体系中加入0.1 g转氨酶酶粉、或由0.1 g转氨酶酶粉对应酶液制备的固定化酶,在47 ℃搅拌20 h。体系经HPLC检测转化率,每一轮反应结束后将固定化酶分离,投入下一轮反应中重复使用,考察重复使用次数。反应数据如下:
转氨酶来源于Transaminase from Aspergillus fumigatus,具有以下序列:
SEQ ID NO:1:
MQKQRTCSQWRELDAAHHLHPFTDTASLNQAGARVMTRGEGVYLWDCEGNKIIDGMAGLWCVNVGYGRKDFAEAARRQMEELPFYNTFFGTTHPPVVELSSLLAEVTPAGFDRVFYTNSGSESVDTMIRMVRRYWDVQGKPEKKTLIGRWNGYHGSTIGGASLGGMKYMHEQGDLPIPGMAHIEQPWWYKHGKDMTPDEFGVVAARWLEEKILEIGADKVAAFVGEPIQGAGGVIVPPATYWPEIERICRKYDVLLVADEVICGFGRTGEWFGHQHFGFQPDLFTAAKGLSSGYLPLGAVFVGDRVAEGLIAGGDFNHGFTYSGHPVCAAVAHANVAALRDEGIVQRVKDDIGPYMQKRWRETFSRFEHVDDVRGVGMMLAFTLVKNKAKRELFPDFGEIGTLCEDIFFRNNLIMTAQGDHIVSAPPLVMTRAEVDEMLAVAERCLEEFEQTLKARGLA。
应用实施例2
MP-PVA-NH2和MP-PVA-CC固定氨基酸脱氢酶(AADH)活性及重复使用性测试:
酶催化反应路线如下:
在10 mL的反应瓶中,加入5 mL 0.1 M Tris-Cl(pH 8.0),随后加入100 mg 主原料,108 mg 氯化铵,调节 pH 值至7.5,接着加10 mg 烟酰胺腺嘌呤二核苷酸(NAD+)、50 mg葡萄糖脱氢酶(GDH:glucose 1-dehydrogenase from Lysinibacillus sphaericus G10,辅酶,用来循环NADP)形成待反应体系;
分别独立地向待反应体系中加入100 mg AADH酶(或者由100 mg 游离酶对应酶液制备的固定化的AADH)。在30 ℃下反应20 h后用于转化率测试。测试结果见下表。
氨基酸脱氢酶来源于Leucine Dehydrogenase from Bacillus cereus,具有以下序列:
SEQ ID NO:2:
MRDVFEMMDRYGHEQVIFCRHPQTGLKAIIALHNTTAGPALGGCRMIPYASTDEALEDVLRLSKGMTYKCSLADVDFGGGKMVIIGDPKKDKSPELFRVIGRFVGGLNGRFYTGTDMGTNPEDFVHAARESKSFAGLPKSYGGKGDTSIPTALGVFHGMRATARFLWGTDQLKGRVVAIQGVGKVGERLLQLLVEVGAYCKIADIDSVRCEQLKEKYGDKVQLVDVNRIHKESCDIFSPCAKGGVVNDDTIDEFRCLAIVGSANNQLVEDRHGALLQKRSICYAPDYLVNAGGLIQVADELEGFHEERVLAKTEAIYDMVLDIFHRAKNENITTCEAADRIVMERLKKLTDIRRILLEDPRNSARR。
应用实施例3
MP-PVA-NH2和MP-PVA-CC固定酮还原酶(KRED)活性及重复使用性测试:
酶催化反应路线如下:
在10 mL的反应瓶中,加入0.5 mL异丙醇(IPA),溶解0.1 g主原料,并加入0.5 mL0.1 M PB 7.0和10 mg 烟酰胺腺嘌呤二核苷酸(NAD+),形成待反应体系;
分别独立地向待反应体系中加入0.05 g酮还原酶酶粉或由0.05 g酮还原酶酶粉对应酶液制备的固定化酶,在30℃搅拌20 h。体系经HPLC检测转化率,每一轮反应结束后将固定化酶分离,投入下一轮反应中重复使用,考察重复使用次数。反应数据如下:
酮还原酶来源于Ketoreductase from Candida macedoniensis AKU4588,具有以下序列:
SEQ ID NO:3:
MKAIQYTRIGAEPELTEIPKPEPGPGEVLLEVTAAGVCHSDDFIMSLPEEQYTYGLPLTLGHEGAGKVAAVGEGVEGLDIGTNVVVYGPWGCGNCWHCSQGLENYCSRAQELGINPPGLGAPGALAEFMIVDSPRHLVPIGDLDPVKTVPLTDAGLTPYHAIKRSLPKLRGGSYAVVIGTGGLGHVAIQLLRHLSAATVIALDVSADKLELATKVGAHEVVLSDKDAAENVRKITGSQGAALVLDFVGYQPTIDTAMAVAGVGSDVTIVGIGDGQAHAKVGFFQSPYEASVTVPYWGARNELIELIDLAHAGIFDIAVETFSLDNGAEAYRRLAAGTLSGRAVVVPGL。
应用实施例4
MP-PVA-NH2和MP-PVA-CC固定单加氧酶(CHMO)活性及重复使用性测试:
酶催化反应路线如下:
0.3 mL的异丙醇装入10 mL的反应瓶中,随后加入500 mg的主原料,3 mL含有5 mgNADP +的0.1 M PB(pH 8.0),然后加入50 mg 醇脱氢酶(ADH-Tb:Alcohol Dehydrogenasefrom Thermoanaerobium brockii,辅酶,用来循环NADP)及100 mg的单加氧酶酶粉(或者由100 mg 游离酶对应酶液制备的固定化的单加氧酶)。在30 ℃下反应20 h,测试转化率,每一轮反应结束后将固定化酶分离,投入下一轮反应中重复使用,考察重复使用次数。结果见下表。
单加氧酶来源于Cyclohexanone monooxygenase from Brachymonas petroleovorans,具有以下序列:
SEQ ID NO:4:
MTTSIDREALRRKYAEERDKRIRPDGNDQYIRLDHVDGWSHDPYMPITPREPKLDHVTFAFIGGGFSGLVTAARLRESGVESVRIIDKAGDFGGVWYWNRYPGAMCDTAAMVYMPLLEETGYMPTEKYAHGPEILEHCQRIGKHYDLYDDALFHTEVTDLVWQEHDQRWRISTNRGDHFTAQFVGMGTGPLHVAQLPGIPGIESFRGKSFHTSRWDYDYTGGDALGAPMDKLADKRVAVIGTGATAVQCVPELAKYCRELYVVQRTPSAVDERGNHPIDEKWFAQIATPGWQKRWLDSFTAIWDGVLTDPSELAIEHEDLVQDGWTALGQRMRAAVGSVPIEQYSPENVQRALEEADDEQMERIRARVDEIVTDPATAAQLKAWFRQMCKRPCFHDDYLPAFNRPNTHLVDTGGKGVERITENGVVVAGVEYEVDCIVYASGFEFLGTGYTDRAGFDPTGRDGVKLSEHWAQGTRTLHGMHTYGFPNLFVLQLMQGAALGSNIPHNFVEAARVVAAIVDHVLSTGTSSVETTKEAEQAWVQLLLDHGRPLGNPECTPGYYNNEGKPAELKDRLNVGYPAGSAAFFRMMDHWLAAGSFDGLTFR。
应用实施例5
MP-PVA-NH2和MP-PVA-CC固定烯还原酶(ERED)活性及重复使用性测试
酶催化反应路线如下:
3 mL的0.1 M 磷酸二氢钠缓冲盐溶液(pH 7.0)装入10 mL的反应瓶中,随后通过加入100 mg的底物,接着加入 10 mg 烟酰胺腺嘌呤二核苷磷酸(NADP+),80 mg甲酸铵,20mg 甲酸脱氢酶(FDH: Formate Dehydrogenase from Candida Boidinii,辅酶,用来循环NADP),形成待反应体系;
分别独立地向待反应体系中加入100 mg的ERED酶(或者由100 mg 游离酶对应酶液制备的固定化的ERED酶)。在30 ℃下反应20 h,测试转化率,每一轮反应结束后将固定化酶分离,投入下一轮反应中重复使用,考察重复使用次数。测试结果见下表。
烯还原酶来源于Ene Reductase from Saccharomyces cerevisiae,具有以下序列:
SEQ ID NO:5:
MNTMLFSPYTIRGLTLKNRIVMSPMCMYSCDTKDGAVRTWHKIHYPARAVGQVGLIIVEATGVTPQGRISERDLGIWSDDHIAGLRELVGLVKEHGAAIGIQLAHAGRKSQVPGEIIAPSAVPFDDSSPTPKEMTKADIEETVQAFQNGARRAKEAGFDVIEIHAAHGYLINEFLSPLSNRRQDEYGGSPENRYRFLGEVIDAVREVWDGPLFVRISASDYHPDGLTAKDYVPYAKRMKEQGVDLVDVSSGAIVPARMNVYPGYQVPFAELIRREADIPTGAVGLITSGWQAEEILQNGRADLVFLGRELLRNPYWPYAAARELGAKISAPVQYERGWRF。
以上所述仅为本发明的优选实施例而已,并不用于限制本发明,对于本领域的技术人员来说,本发明可以有各种更改和变化。凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
序列表
<110> 凯莱英医药集团(天津)股份有限公司
<120> 酶固定化载体及其制备方法、固定化酶及其制备方法
<130> PN147916KLY
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<170> SIPOSequenceListing 1.0
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Gly Glu Pro Ile Gln Gly Ala Gly Gly Val Ile Val Pro Pro Ala Thr
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Val Ala Asp Glu Val Ile Cys Gly Phe Gly Arg Thr Gly Glu Trp Phe
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Gly His Gln His Phe Gly Phe Gln Pro Asp Leu Phe Thr Ala Ala Lys
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Gly Leu Ser Ser Gly Tyr Leu Pro Leu Gly Ala Val Phe Val Gly Asp
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Arg Val Ala Glu Gly Leu Ile Ala Gly Gly Asp Phe Asn His Gly Phe
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Thr Tyr Ser Gly His Pro Val Cys Ala Ala Val Ala His Ala Asn Val
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Ala Ala Leu Arg Asp Glu Gly Ile Val Gln Arg Val Lys Asp Asp Ile
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Gly Pro Tyr Met Gln Lys Arg Trp Arg Glu Thr Phe Ser Arg Phe Glu
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His Val Asp Asp Val Arg Gly Val Gly Met Met Leu Ala Phe Thr Leu
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Ala Gln Gly Asp His Ile Val Ser Ala Pro Pro Leu Val Met Thr Arg
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His Asn Thr Thr Ala Gly Pro Ala Leu Gly Gly Cys Arg Met Ile Pro
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Phe Arg Val Ile Gly Arg Phe Val Gly Gly Leu Asn Gly Arg Phe Tyr
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Thr Gly Thr Asp Met Gly Thr Asn Pro Glu Asp Phe Val His Ala Ala
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Arg Glu Ser Lys Ser Phe Ala Gly Leu Pro Lys Ser Tyr Gly Gly Lys
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Gly Asp Thr Ser Ile Pro Thr Ala Leu Gly Val Phe His Gly Met Arg
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Ala Thr Ala Arg Phe Leu Trp Gly Thr Asp Gln Leu Lys Gly Arg Val
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Val Ala Ile Gln Gly Val Gly Lys Val Gly Glu Arg Leu Leu Gln Leu
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Leu Val Glu Val Gly Ala Tyr Cys Lys Ile Ala Asp Ile Asp Ser Val
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Asp Val Asn Arg Ile His Lys Glu Ser Cys Asp Ile Phe Ser Pro Cys
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Ala Lys Gly Gly Val Val Asn Asp Asp Thr Ile Asp Glu Phe Arg Cys
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Gly Ala Leu Leu Gln Lys Arg Ser Ile Cys Tyr Ala Pro Asp Tyr Leu
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His Glu Glu Arg Val Leu Ala Lys Thr Glu Ala Ile Tyr Asp Met Val
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His Cys Ser Gln Gly Leu Glu Asn Tyr Cys Ser Arg Ala Gln Glu Leu
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Gly Ile Asn Pro Pro Gly Leu Gly Ala Pro Gly Ala Leu Ala Glu Phe
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Met Ile Val Asp Ser Pro Arg His Leu Val Pro Ile Gly Asp Leu Asp
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Pro Val Lys Thr Val Pro Leu Thr Asp Ala Gly Leu Thr Pro Tyr His
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Ala Ile Lys Arg Ser Leu Pro Lys Leu Arg Gly Gly Ser Tyr Ala Val
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Val Ile Gly Thr Gly Gly Leu Gly His Val Ala Ile Gln Leu Leu Arg
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His Leu Ser Ala Ala Thr Val Ile Ala Leu Asp Val Ser Ala Asp Lys
195 200 205
Leu Glu Leu Ala Thr Lys Val Gly Ala His Glu Val Val Leu Ser Asp
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Leu Ile Asp Leu Ala His Ala Gly Ile Phe Asp Ile Ala Val Glu Thr
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Glu Arg Asp Lys Arg Ile Arg Pro Asp Gly Asn Asp Gln Tyr Ile Arg
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Leu Asp His Val Asp Gly Trp Ser His Asp Pro Tyr Met Pro Ile Thr
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Pro Arg Glu Pro Lys Leu Asp His Val Thr Phe Ala Phe Ile Gly Gly
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Gly Phe Ser Gly Leu Val Thr Ala Ala Arg Leu Arg Glu Ser Gly Val
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Glu Ser Val Arg Ile Ile Asp Lys Ala Gly Asp Phe Gly Gly Val Trp
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Tyr Trp Asn Arg Tyr Pro Gly Ala Met Cys Asp Thr Ala Ala Met Val
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Tyr Met Pro Leu Leu Glu Glu Thr Gly Tyr Met Pro Thr Glu Lys Tyr
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Ala His Gly Pro Glu Ile Leu Glu His Cys Gln Arg Ile Gly Lys His
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Tyr Asp Leu Tyr Asp Asp Ala Leu Phe His Thr Glu Val Thr Asp Leu
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Val Trp Gln Glu His Asp Gln Arg Trp Arg Ile Ser Thr Asn Arg Gly
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Asp His Phe Thr Ala Gln Phe Val Gly Met Gly Thr Gly Pro Leu His
180 185 190
Val Ala Gln Leu Pro Gly Ile Pro Gly Ile Glu Ser Phe Arg Gly Lys
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Ser Phe His Thr Ser Arg Trp Asp Tyr Asp Tyr Thr Gly Gly Asp Ala
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Leu Gly Ala Pro Met Asp Lys Leu Ala Asp Lys Arg Val Ala Val Ile
225 230 235 240
Gly Thr Gly Ala Thr Ala Val Gln Cys Val Pro Glu Leu Ala Lys Tyr
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Cys Arg Glu Leu Tyr Val Val Gln Arg Thr Pro Ser Ala Val Asp Glu
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Arg Gly Asn His Pro Ile Asp Glu Lys Trp Phe Ala Gln Ile Ala Thr
275 280 285
Pro Gly Trp Gln Lys Arg Trp Leu Asp Ser Phe Thr Ala Ile Trp Asp
290 295 300
Gly Val Leu Thr Asp Pro Ser Glu Leu Ala Ile Glu His Glu Asp Leu
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Val Gln Asp Gly Trp Thr Ala Leu Gly Gln Arg Met Arg Ala Ala Val
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Gly Ser Val Pro Ile Glu Gln Tyr Ser Pro Glu Asn Val Gln Arg Ala
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Leu Glu Glu Ala Asp Asp Glu Gln Met Glu Arg Ile Arg Ala Arg Val
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Asp Glu Ile Val Thr Asp Pro Ala Thr Ala Ala Gln Leu Lys Ala Trp
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Phe Arg Gln Met Cys Lys Arg Pro Cys Phe His Asp Asp Tyr Leu Pro
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Ala Phe Asn Arg Pro Asn Thr His Leu Val Asp Thr Gly Gly Lys Gly
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Val Glu Arg Ile Thr Glu Asn Gly Val Val Val Ala Gly Val Glu Tyr
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Glu Val Asp Cys Ile Val Tyr Ala Ser Gly Phe Glu Phe Leu Gly Thr
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Gly Tyr Thr Asp Arg Ala Gly Phe Asp Pro Thr Gly Arg Asp Gly Val
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Lys Leu Ser Glu His Trp Ala Gln Gly Thr Arg Thr Leu His Gly Met
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His Thr Tyr Gly Phe Pro Asn Leu Phe Val Leu Gln Leu Met Gln Gly
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Ala Ala Gly Ser Phe Asp Gly Leu Thr Phe Arg
595 600
<210> 5
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<212> PRT
<213> Ene Reductase from Saccharomyces cerevisiae
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Met Asn Thr Met Leu Phe Ser Pro Tyr Thr Ile Arg Gly Leu Thr Leu
1 5 10 15
Lys Asn Arg Ile Val Met Ser Pro Met Cys Met Tyr Ser Cys Asp Thr
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Lys Asp Gly Ala Val Arg Thr Trp His Lys Ile His Tyr Pro Ala Arg
35 40 45
Ala Val Gly Gln Val Gly Leu Ile Ile Val Glu Ala Thr Gly Val Thr
50 55 60
Pro Gln Gly Arg Ile Ser Glu Arg Asp Leu Gly Ile Trp Ser Asp Asp
65 70 75 80
His Ile Ala Gly Leu Arg Glu Leu Val Gly Leu Val Lys Glu His Gly
85 90 95
Ala Ala Ile Gly Ile Gln Leu Ala His Ala Gly Arg Lys Ser Gln Val
100 105 110
Pro Gly Glu Ile Ile Ala Pro Ser Ala Val Pro Phe Asp Asp Ser Ser
115 120 125
Pro Thr Pro Lys Glu Met Thr Lys Ala Asp Ile Glu Glu Thr Val Gln
130 135 140
Ala Phe Gln Asn Gly Ala Arg Arg Ala Lys Glu Ala Gly Phe Asp Val
145 150 155 160
Ile Glu Ile His Ala Ala His Gly Tyr Leu Ile Asn Glu Phe Leu Ser
165 170 175
Pro Leu Ser Asn Arg Arg Gln Asp Glu Tyr Gly Gly Ser Pro Glu Asn
180 185 190
Arg Tyr Arg Phe Leu Gly Glu Val Ile Asp Ala Val Arg Glu Val Trp
195 200 205
Asp Gly Pro Leu Phe Val Arg Ile Ser Ala Ser Asp Tyr His Pro Asp
210 215 220
Gly Leu Thr Ala Lys Asp Tyr Val Pro Tyr Ala Lys Arg Met Lys Glu
225 230 235 240
Gln Gly Val Asp Leu Val Asp Val Ser Ser Gly Ala Ile Val Pro Ala
245 250 255
Arg Met Asn Val Tyr Pro Gly Tyr Gln Val Pro Phe Ala Glu Leu Ile
260 265 270
Arg Arg Glu Ala Asp Ile Pro Thr Gly Ala Val Gly Leu Ile Thr Ser
275 280 285
Gly Trp Gln Ala Glu Glu Ile Leu Gln Asn Gly Arg Ala Asp Leu Val
290 295 300
Phe Leu Gly Arg Glu Leu Leu Arg Asn Pro Tyr Trp Pro Tyr Ala Ala
305 310 315 320
Ala Arg Glu Leu Gly Ala Lys Ile Ser Ala Pro Val Gln Tyr Glu Arg
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Gly Trp Arg Phe
340
Claims (20)
1.一种酶固定化载体,其特征在于,所述酶固定化载体为超交联聚乙烯醇经氨基修饰或三聚氯氰修饰得到,所述氨基修饰采用3-氨丙基三乙氧基硅烷为氨基修饰试剂。
2.根据权利要求1所述的酶固定化载体,其特征在于,所述超交联聚乙烯醇为聚乙烯醇依次经氧化、自交联、交联剂交联得到。
3.一种固定化酶,其特征在于,所述固定化酶由权利要求1或2所述的酶固定化载体和酶经共价连接形成。
4.根据权利要求3所述的固定化酶,其特征在于,所述酶选自转氨酶、单加氧酶、酮还原酶、烯还原酶、氨基酸脱氢酶中的任意一种或多种;
所述转氨酶为来源于Chromobacterium violaceum DSM30191的转氨酶或者来源于Arthrobacter citreus的转氨酶,或来源于B.thuringiensis的转氨酶;
所述单加氧酶为来源于Brachymonas petroleovorans的环己酮单加氧酶,或者来源于 Rhodococcus ruber-SD1的环己酮单加氧酶;
所述酮还原酶为来源于Acetobacter sp. CCTCC M209061的酮还原酶,或者来源于Candida macedoniensis AKU4588的酮还原酶;
所述烯还原酶为来源于Saccharomyces cerevisiae的烯还原酶和来源于 Chryseobacterium sp. CA49的烯还原酶;
所述氨基酸脱氢酶为来源于Bacillus cereus的亮氨酸脱氢酶和来源于Bacillus sphaericus的苯丙氨酸脱氢酶。
5.一种权利要求1或2所述的酶固定化载体的制备方法,其特征在于,包括以下步骤:
提供超交联聚乙烯醇;
将所述超交联聚乙烯醇进行氨基修饰或三聚氯氰修饰,得到所述酶固定化载体;所述氨基修饰采用3-氨丙基三乙氧基硅烷为氨基修饰试剂。
6.根据权利要求5所述的酶固定化载体的制备方法,其特征在于,所述超交联聚乙烯醇由以下方法制备得到:
氧化步骤:将聚乙烯醇溶解于水中,其次加入氧化剂进行氧化反应,得到氧化产物体系;
自交联步骤:用盐酸调节所述氧化产物体系的氯化氢浓度在0.1~1 mol/L,然后在70~90℃温度下进行自交联反应,得到聚乙烯醇凝胶颗粒;
交联剂交联步骤:将所述聚乙烯凝胶颗粒分散在水中,其次加入交联剂进行反应,得到所述超交联聚乙烯醇。
7.根据权利要求6所述的酶固定化载体的制备方法,其特征在于,所述氧化剂为高碘酸钠;所述氧化反应的温度为20~30℃。
8.根据权利要求6所述的酶固定化载体的制备方法,其特征在于,所述交联剂为浓度为2~10wt%的戊二醛溶液所述交联剂交联步骤的反应温度为40~60℃,且期间加入盐酸使体系中氯化氢浓度在0.1~1 mol/L。
9.根据权利要求5至8中任一项所述的酶固定化载体的制备方法,其特征在于,将所述超交联聚乙烯醇进行所述氨基修饰的步骤包括:
将所述超交联聚乙烯醇、第一溶剂、所述氨基修饰试剂混合并进行反应,得到所述酶固定化载体。
10.根据权利要求9所述的酶固定化载体的制备方法,其特征在于,所述氨基修饰的反应过程中,相对于每克所述超交联聚乙烯醇,所述氨基修饰试剂的加入量为0.3~1 mL。
11.根据权利要求10所述的酶固定化载体的制备方法,其特征在于,所述氨基修饰的反应过程中,反应pH值为2~3,反应温度为60~90℃。
12.根据权利要求5至8中任一项所述的酶固定化载体的制备方法,其特征在于,将所述超交联聚乙烯醇进行所述三聚氯氰修饰的步骤包括:
将所述超交联聚乙烯醇分散于第二溶剂,其次加入三聚氯氰进行反应,得到所述酶固定化载体。
13.根据权利要求12所述的酶固定化载体的制备方法,其特征在于,相对于每克所述超交联聚乙烯醇,所述三聚氯氰的加入量为0.25~1g。
14.根据权利要求12所述的酶固定化载体的制备方法,其特征在于,所述三聚氯氰修饰的反应过程中,反应温度为0~10℃。
15.一种权利要求3或4所述的固定化酶的制备方法,其特征在于,包括以下步骤:将权利要求1或2所述的酶固定化载体和酶进行共价连接,得到所述固定化酶。
16.根据权利要求15所述的固定化酶的制备方法,其特征在于,当所述酶固定化载体为超交联聚乙烯醇经氨基修饰得到时,所述固定化酶的制备方法包括以下步骤:
将所述酶固定化载体分散于戊二醛溶液中进行活化,得到活化载体;
将所述活化载体与含酶的酶液进行反应,以使所述酶与所述酶固定化载体共价连接,得到所述固定化酶。
17.根据权利要求16所述的固定化酶的制备方法,其特征在于,所述戊二醛溶液为质量浓度为1~2%。
18.根据权利要求17所述的固定化酶的制备方法,其特征在于,所述活化步骤中,活化温度为20~30℃,活化时间为1~3 h;所述活化载体与所述酶液进行反应的过程中,反应温度为20~30℃;每克所述活化载体对应2~6 mL所述酶液,且所述酶液中的蛋白含量为30~40mg/mL。
19.根据权利要求15所述的固定化酶的制备方法,其特征在于,当所述酶固定化载体为超交联聚乙烯醇经三聚氯氰修饰得到时,所述固定化酶的制备方法包括以下步骤:
采用磷酸盐缓冲液将所述酶固定化载体进行润湿;
将润湿后的所述酶固定化载体与含酶的酶液进行反应,以使所述酶与所述酶固定化载体共价连接,得到所述固定化酶。
20.根据权利要求19所述的固定化酶的制备方法,其特征在于,将润湿后的所述酶固定化载体与所述酶液进行反应的过程中,反应温度为20~30℃;每克所述酶固定化载体对应2~6 mL所述酶液,且所述酶液中的蛋白含量为30~40 mg/mL。
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