CN110184288A - 没食子酸和原儿茶酸的制备方法及其反应催化剂的制备方法 - Google Patents
没食子酸和原儿茶酸的制备方法及其反应催化剂的制备方法 Download PDFInfo
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- CN110184288A CN110184288A CN201910452089.8A CN201910452089A CN110184288A CN 110184288 A CN110184288 A CN 110184288A CN 201910452089 A CN201910452089 A CN 201910452089A CN 110184288 A CN110184288 A CN 110184288A
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Classifications
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- C12N15/66—General methods for inserting a gene into a vector to form a recombinant vector using cleavage and ligation; Use of non-functional linkers or adaptors, e.g. linkers containing the sequence for a restriction endonuclease
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- C12N15/70—Vectors or expression systems specially adapted for E. coli
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
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- C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
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- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
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Abstract
本发明公开了一种没食子酸和原儿茶酸的制备方法及其反应催化剂的制备方法，通过对3‑脱氢莽草酸脱水酶基因aroZ片段或者对羟苯甲酸羟化酶基因pobA片段进行构建，形成有催化性质的酶液，然后进行生物合成反应，合成原儿茶酸和没食子酸；本发明的有益效果：以葡萄糖为原料，其价格实惠，来源广泛，而且整个工艺得到了简化，减少环境污染，降低没食子酸生产成本。
Description
技术领域
本发明涉及使用酶催化的方法来制取芳环化合物衍生物的技术，具体而言，涉及生物法生产没食子酸的工艺。
背景技术
没食子酸又名倍酸、五倍子酸(gallic acid)，化学名称为3，4，5-三羟基苯甲酸(3,4,5-trihydroxy benzonic acid)，白色针状结晶，是一种用途广泛的化学品。
目前，没食子酸的生产工艺主要有三种：
化学水解法：以五倍子为原料，通过强酸或者强碱为催化剂，使得五倍子丹宁水解生成没食子酸，然后经过过滤、浓缩、脱色和干燥等一系列化工过程制的产品。此工艺操作简单，但是由于强酸强碱对环境污染大、原料来源受环境影响较大，产品回收率低等原因，目前已经处于淘汰状态。
一步法微生物发酵法：专利CN87103987中报道利用微生物在含有单宁的水溶液中进行发酵，以单宁酸水解后的葡萄糖作为微生物生长的碳源，维持微生物的生长、增殖，同时微生物生产出酶催化单宁生成没食子酸。此方法单宁水解不完全，收率低，发酵周期长，成本不适合产业化生产。
两步发酵法：CN93107994中报道使用黑曲霉发酵生产单宁酶，将单宁酶的发酵和单宁的催化分开进行，先培养黑曲霉至菌丝体浓度达到一定值，然后加入单宁，使得黑曲霉生长、单宁催化同时进行，单宁转化率可达到98%，显著降低了原料单耗，合理的利用植物单宁资源。
以上三种没食子酸的制备方法中，各有优点，但是，它们共同的缺点是利用植物资源单宁为原料生产没食子酸，植物资源的生长有一定周期，同时随着人力成本的上升，植物来源单宁价格不断上涨，导致没食子酸生产成本提高。
发明内容
为了解决上述问题，本发明提供了一种没食子酸和原儿茶酸的制备方法及其反应催化剂的制备方法，具体技术方案如下：
一种酶催化剂的制备方法，具体步骤如下：
步骤一：将3-脱氢莽草酸脱水酶基因aroZ片段或者对羟苯甲酸羟化酶基因pobA片段重组到pET21a载体上，阳性重组质粒aroZ-pET21a(+)或者阳性重组质粒pobA-pET21a(+)转化表达宿主菌BL21(DE3)，得到原核表达菌株aroZ-pET21a(+)/ BL21(DE3)或者原核表达菌株pobA-pET21a(+)/ BL21(DE3)；
步骤二：将上述表达菌株在加有终浓度为100ug/mL氨苄青霉素的5mL LB液体培养基中于37℃、200rpm振荡培养过夜后，按1%(V/V)比例接种于含有终浓度为100ug/mL氨苄青霉素的500mL LB液体培养基中，于37℃、200rpm振荡培养。待OD600在0.8-1.0之间时，加入终浓度为0.1mM的诱导剂IPTG(异丙基-β-D-硫代半乳糖苷，IPTG)，并在25℃诱导过夜；
步骤三：将步骤二所得液在8000rpm条件下离心收集，然后悬浮于50mM pH7.0 磷酸钠缓冲液中，超声破碎(200W，3s/5s，10min)，4℃，12000rpm离心20min，得到3-脱氢莽草酸脱水酶催化剂或者对羟苯甲酸羟化酶催化剂。
优选地，其特征在于：所述步骤二中的培养基包括：10g/L 胰蛋白胨(OXIOD)，5g/L酵母粉(OXIOD)，10g/L 氯化钠（国药试剂）。
本发明中，3-脱氢莽草酸脱水酶来源于Pseudomonas parafulva副黄假单胞菌，对羟苯甲酸羟化酶来源于大肠杆菌。
该酶作为催化剂的形态可以是：纯酶、相应的重组菌休止细胞、粗酶液或者粗酶粉等。
一种制备原儿茶酸的方法，具体步骤如下：
步骤一：将葡萄糖发酵得到3-脱氢莽草酸；
步骤二：将步骤一得到的3-脱氢莽草酸溶解并加入磷酸盐，调整PH到6-11，加入权1中的3-脱氢莽草酸脱水酶催化剂；（实施例7中ph为6）
步骤三：将步骤二中的反应体系在25-40℃下恒温搅拌，反应1-5小时，得到原儿茶酸。
优选地，其特征在于：所述步骤二中加入磷酸盐至最终浓度为50mM。
原儿茶酸（PCA）是采用3-脱氢莽草酸(DHS)脱水酶进行的生物催化反应，反应方程式为：
反应体系为：3-脱氢莽草酸脱水酶，磷酸缓冲液，3-脱氢莽草酸，氯化钠。具体的为:酶的用量在1-10g/L，缓冲液浓度在50-200mM，缓冲液pH值在6.0-8.5之间，氯化钠浓度在10-100mmol之间，底物浓度在30-100g/L之间。反应后产物通过乙腈淬灭后经高效液相色谱(HPLC)验证，反应转化率可达90%，或95%，或99%以上，产物的纯度值可达90%，或95%，或99%以上。
一种没食子酸的制备方法，具体步骤如下：
步骤一：取权利要求3中所得的原儿茶酸溶解于磷酸盐的水溶液中，调节pH到6-11,；
步骤二：向步骤一种的体系中加入权1中的对羟苯甲酸羟化酶催化剂；
步骤三：将步骤二中的反应体系在25-40℃下恒温搅拌，反应24小时以上，得到没食子酸。
优选地，其特征在于：所述步骤一种磷酸盐浓度为50mM。
没食子酸(GA)在原儿茶酸(PCA)的基础上，采用对羟苯甲酸羟化酶进行的生物催化反应，反应方程式为：
反应体系为：对羟苯甲酸羟化酶，磷酸缓冲液，原儿茶酸，核黄素或者FAD之类的辅助因子。具体的为:酶的用量在1-10g/L，缓冲液浓度在50-200mM，缓冲液pH值在6.0-8.5之间，底物浓度在5-20g/L之间。反应后产物通过乙腈淬灭后经高效液相色谱(HPLC)验证，反应转化率可达90%，或95%，或99%以上，产物的纯度值可达90%，或95%，或99%以上。
本发明中使用以葡萄糖为原料发酵得到的3-脱氢莽草酸为底物，经过酶催化生成原儿茶酸，再经过酶催化可以得到没食子酸，解决了已有方法中原料来源问题，同时显著简化工艺，减少环境污染，降低没食子酸生产成本。
附图说明
图1为实施例3中HPLC检测图；
图2为实施例4中HPLC检测图；
图3为实施例5中HPLC检测图；
图4为实施例6中HPLC检测图；
图5为实施例7中HPLC检测图；
图6为实施例8中HPLC检测图；
图7为实施例9中HPLC检测图。
具体实施方式
为了加深对本发明的理解，下面将结合实施例对本发明做进一步详细描述，该实施例仅用于解释本发明，并不对保护范围构成限定。
实施例1 原核表达体系的构建
3-脱氢莽草酸脱水酶基因aroZ片段由南京金斯瑞生物科技有限公司合成，并重组到pET21a载体上。将阳性重组质粒aroZ-pET21a(+)转化表达宿主菌BL21(DE3)(购自天根生化科技(北京)有限公司)，得到原核表达菌株aroZ-pET21a(+)/ BL21(DE3)，作为后续催化反应原代菌株。
对羟苯甲酸羟化酶基因pobA片段由南京金斯瑞生物科技有限公司合成，并重组到pET21a载体上。将阳性重组质粒pobA-pET21a(+)转化表达宿主菌BL21(DE3)(购自天根生化科技(北京)有限公司)，得到原核表达菌株pobA-pET21a(+)/ BL21(DE3)，作为后续催化反应原代菌株。
实施例2 酶的发酵制备
上述构建的表达菌株aroZ-pET21a(+)/ BL21(DE3)、pobA-pET21a(+)/ BL21(DE3)在加有终浓度为100ug/mL氨苄青霉素的5mL LB液体培养基【10g/L 胰蛋白胨(OXIOD)，5g/L 酵母粉(OXIOD)，10g/L 氯化钠（国药试剂）】中于37℃、200rpm振荡培养过夜后，按1%(V/V)比例接种于含有终浓度为100ug/mL氨苄青霉素的500mL LB液体培养基中，于37℃、200rpm振荡培养。待OD600在0.8-1.0之间时，加入终浓度为0.1mM的诱导剂IPTG(异丙基-β-D-硫代半乳糖苷，IPTG)，并在25℃诱导过夜。菌体在8000rpm条件下离心收集，然后悬浮于50mMpH7.0 磷酸钠缓冲液中，超声破碎(200W，3s/5s，10min)，4℃，12000rpm离心20min，取上清备用。
实施例3
在含有50g底物I(3-脱氢莽草酸)的水溶液800ml中加入磷酸盐至终浓度为50mM，溶液pH值达到7.0，待搅拌溶解后加入3-脱氢莽草酸脱水酶酶液200mL使得终体积为1L。反应液置于37℃恒温水浴锅中，机械搅拌反应。反应1h后进行HPLC检测，底物转化率>98%，见图1。
实施例4
在含有60g底物I(3-脱氢莽草酸)的水溶液800ml中加入磷酸盐至终浓度为50mM，溶液pH值达到7.0，待搅拌溶解后加入3-脱氢莽草酸脱水酶酶液200mL使得终体积为1L。反应液置于37℃恒温水浴锅中，机械搅拌反应。反应1.5h后进行HPLC检测，底物转化率>98%，见图2。
实施例5
在含有60g底物I(3-脱氢莽草酸)的水溶液800ml中加入磷酸盐至终浓度为50mM，溶液pH值达到6.0，待搅拌溶解后加入3-脱氢莽草酸脱水酶酶液200mL使得终体积为1L。反应液置于37℃恒温水浴锅中，机械搅拌反应。反应5h后进行HPLC检测，底物转化率>98%，见图3。
实施例6
将10g底物原料II(原儿茶酸)溶解于800mL磷酸盐浓度为50mM的水溶液终，调节pH至pH7.0，待搅拌溶解后加入对羟苯甲酸羟化酶酶液200ml，反应终体积为1L。反应液置于37℃恒温水浴锅中，机械搅拌反应。反应24h后进行HPLC检测，底物转化率>85%，见图4。
实施例7
将2g底物原料II(原儿茶酸)溶解于800mL磷酸盐浓度为50mM的水溶液终，调节pH至pH7.0，待搅拌溶解后加入对羟苯甲酸羟化酶酶液200ml，反应终体积为1L。反应液置于37℃恒温水浴锅中，机械搅拌反应。反应24h后进行HPLC检测，底物转化率>90%，见图5。
实施例8
将2g底物原料II(原儿茶酸)溶解于800mL磷酸盐浓度为50mM的水溶液终，调节pH至pH6.0，待搅拌溶解后加入对羟苯甲酸羟化酶酶液200ml，反应终体积为1L。反应液置于37℃恒温水浴锅中，机械搅拌反应。反应24h后进行HPLC检测，底物转化率>95%，见图6。
实施例9
将2g底物原料II(原儿茶酸)溶解于800mL磷酸盐浓度为50mM的水溶液终，调节pH至pH7.0，待搅拌溶解后加入对羟苯甲酸羟化酶酶液200ml，反应终体积为1L。反应液置于30℃恒温水浴锅中，机械搅拌反应。反应24h后进行HPLC检测，底物转化率>98%，见图7。
实施例10 HPLC检测方法建立
底物转化率的检测通过HPLC进行，检测的条件如下：仪器为安捷伦HPLC1100、液相柱为安捷伦Agllent 5 TC-C18(2) 250*4.6mm、流动相Buffer A为纯度大于99%的甲醇溶液、流动相Buffer B为0.1%的磷酸水溶液、A相和B相以一定梯度混合，柱温箱温度25°C、流速1mL/min、检测波长254nm、样品浓度2mg/mL、进样量10uL。检测后将产物的峰面积除以产物和底物的峰面积之和，求得转化率。
上述检测样品均采用流动相稀释到合适浓度后，用0.22μm的滤膜过滤进仪器检测。
以上实施例中，未注明具体条件的实验方法，通常按常规条件，如《分子克隆实验指南》（J.萨姆布鲁克，D.W.拉塞尔著，黄培堂，汪嘉玺，朱厚础等译，第三版，北京：科学出版社，2002）中所述的方法进行。
本实施例中涉及一种功能性3-脱氢莽草酸脱水酶（简写为Aro Z），能够进行催化3-脱氢莽草酸合成原儿茶酸，其氨基酸序列衍生自Pseudomonas parafulva副黄假单胞菌，且具有附件所列的序列。本发明还涉及一种功能性对羟苯甲酸羟化酶(简写PobA)，能够催化原儿茶酸合成没食子酸，其氨基酸序列衍生自大肠杆菌，且具有附件所列的序列。
综合上述实施例可知，制得酶之后，再进行构建，形成有催化效果的催化剂，可以用于生物反应中，给没食子酸的制备提供了一条新的路线，以容易获得的葡萄糖为原料发酵得到的3-脱氢莽草酸为底物，经过酶催化生成原儿茶酸，再经过酶催化可以得到没食子酸，解决了已有方法中原料来源问题，同时显著简化工艺，减少环境污染，降低没食子酸生产成本。
序列表
<110> 南京趣酶生物科技有限公司
上海仁酶生物科技有限公司
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Tyr Glu Ser Val Trp Pro Phe Gly Trp Leu Gly Leu Leu Ala Asp Thr
180 185 190
Pro Pro Val Asn Pro Glu Leu Ile Tyr Ala His His Gln Arg Gly Phe
195 200 205
Val Leu Cys Ser Gln Arg Ser Leu Thr Arg Ser Arg Tyr Tyr Leu Gln
210 215 220
Val Pro Leu Ser Asp Lys Val Glu Ala Trp Ser Asp Glu Arg Phe Trp
225 230 235 240
Gln Glu Leu Lys Ser Arg Leu Pro Glu Glu Leu Ala Ser Arg Leu Val
245 250 255
Thr Gly His Ser Leu Glu Lys Ser Ile Ala Pro Leu Arg Ser Phe Val
260 265 270
Val Glu Pro Met Gln Tyr Gly Arg Leu Phe Leu Val Gly Asp Ala Ala
275 280 285
His Ile Val Pro Pro Thr Gly Ala Lys Gly Leu Asn Leu Ala Ala Ser
290 295 300
Asp Val Asn Tyr Leu Trp Arg Ile Leu Arg Glu Tyr Tyr His Arg Gly
305 310 315 320
Arg Ser Asp Leu Leu Ala Ala Tyr Ser Gln Leu Ala Leu Asp Arg Val
325 330 335
Trp Lys Gly Glu Arg Phe Ser Trp Phe Met Thr Arg Leu Leu His Asp
340 345 350
Phe Pro Asp Gln Asn Ala Phe Asp Ala Lys Met Gln Ala Ala Asp Arg
355 360 365
Arg Tyr Tyr Leu Gly Ser Arg Ala Gly Leu Thr Thr Ile Ala Glu Asn
370 375 380
Tyr Val Gly Leu Pro Met Glu Arg Val Ala
385 390
Claims (6)
1.一种酶催化剂的制备方法，具体步骤如下：
步骤一：将3-脱氢莽草酸脱水酶基因aroZ片段或者对羟苯甲酸羟化酶基因pobA片段重组到pET21a载体上，阳性重组质粒aroZ-pET21a(+)或者阳性重组质粒pobA-pET21a(+)转化表达宿主菌BL21(DE3)，得到原核表达菌株aroZ-pET21a(+)/ BL21(DE3)或者原核表达菌株pobA-pET21a(+)/ BL21(DE3)；
步骤二：将上述表达菌株在加有终浓度为100ug/mL氨苄青霉素的5mL LB液体培养基中于37℃、200rpm振荡培养过夜后，按1%(V/V)比例接种于含有终浓度为100ug/mL氨苄青霉素的500mL LB液体培养基中，于37℃、200rpm振荡培养，待OD600在0.8-1.0之间时，加入终浓度为0.1mM的诱导剂IPTG(异丙基-β-D-硫代半乳糖苷，IPTG)，并在25℃诱导过夜；
步骤三：将步骤二所得液在8000rpm条件下离心收集，然后悬浮于50mM pH7.0 磷酸钠缓冲液中，超声破碎(200W，3s/5s，10min)，4℃，12000rpm离心20min，得到3-脱氢莽草酸脱水酶催化剂或者对羟苯甲酸羟化酶催化剂。
2.根据权利要求1所述的一种酶催化剂的制备方法，其特征在于：所述步骤二中的培养基包括：10g/L 胰蛋白胨(OXIOD)，5g/L 酵母粉(OXIOD)，10g/L 氯化钠（国药试剂）。
3.一种制备原儿茶酸的方法，具体步骤如下：
步骤一：将葡萄糖发酵得到3-脱氢莽草酸；
步骤二：将步骤一得到的3-脱氢莽草酸溶解并加入磷酸盐，调整PH到6-11，加入权利要求1中的3-脱氢莽草酸脱水酶催化剂；（实施例7中pH为6）
步骤三：将步骤二中的反应体系在25-40℃下恒温搅拌，反应1-5小时，得到原儿茶酸。
4.根据权利要求3所述的一种制备原儿茶酸的方法，其特征在于：所述步骤二中加入磷酸盐至最终浓度为50mM。
5.一种没食子酸的制备方法，具体步骤如下：
步骤一：取权利要求3中所得的原儿茶酸溶解于磷酸盐的水溶液中，调节pH到6-11,；
步骤二：向步骤一种的体系中加入权利要求1中的对羟苯甲酸羟化酶催化剂；
步骤三：将步骤二中的反应体系在25-40℃下恒温搅拌，反应24小时以上，得到没食子酸。
6.根据权利要求5所述的一种没食子酸的制备方法，其特征在于：所述步骤一种磷酸盐浓度为50mM。
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