CN116855393A - 一种生产fr901379衍生物的基因工程菌及其应用 - Google Patents
一种生产fr901379衍生物的基因工程菌及其应用 Download PDFInfo
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Abstract
本发明公开了一种生产FR901379衍生物的基因工程菌及其应用。所述基因工程菌在出发菌丝状真菌Coleophoma empetri中失活编码α‑酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因,其中所述α‑酮戊二酸依赖性氧化酶为CEOXY1或CEOXY4,所述P450单加氧酶为CEP450‑1、CEP450‑2或CEP450‑3。本发明还公开了所述基因工程菌的构建方法,还公开了FR901379衍生物以及通过培养所述基因工程菌来制备所述FR901379衍生物的方法。本发明利用CRISPR/Cas9的方法对出发菌中参与FR901379合成的基因进行敲除,验证了基因的功能,同时获得了一系列具有生物活性的衍生物,该类衍生物具有一定的成药潜在价值。
Description
技术领域
本发明属于基因工程技术领域,具体涉及一种生产FR901379衍生物的基因工程菌及其应用,所述基因工程菌为失活编码α-酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因的丝状真菌。本发明还涉及利用所述基因工程菌生产的FR901379衍生物。
背景技术
米卡芬净是一种棘白霉素类抗生素,于2006年FDA批准上市,主要用于治疗深部真菌感染。棘白霉素类化合物通过非竞争性抑制细胞壁1,3-β葡聚糖合酶的活性来抑制真菌细胞壁的合成,具有良好的抗真菌活性及毒副作用小的优点。但目前棘白霉素类药物仅有三种,分别是米卡芬净,卡泊芬净和阿尼芬净,对于深部真菌感染的治疗用药较少,因此迫切需要发现更多具有活性的棘白霉素类化合物。
FR901379是合成米卡芬净的关键前体,由丝状真菌Coleophoma empetri F-11899产生,其结构式为:
其生物合成机制尚无报道。
纽莫康定B0(Pneumocandin B0,PB0)是合成卡泊芬净的关键前体,由丝状真菌Glarea lozoyensis产生,其生物合成途径已报道;EcB(Echinocandin B)是合成阿尼芬净的关键前体,由丝状真菌Aspergillus pachycristatus产生,其生物合成途径也已报道。三种化合物都是通过PKS和NRPS途径合成的环脂肽类化合物。
发明内容
为了解决现有技术中需要发现更多具有生物活性的棘白霉素类衍生物,提供了一种生产FR901379衍生物的基因工程菌及其应用。
本发明在丝状真菌Coleophoma empetri F-11899中利用CRISPR/Cas9的方法对参与FR901379合成的基因进行敲除,验证了基因的功能,同时获得了一系列具有生物活性的衍生物,该类衍生物具有一定的成药潜在价值。
为解决上述技术问题,本发明提供的技术方案之一为:一种基因工程菌,所述基因工程菌在出发菌丝状真菌Coleophoma empetri中失活编码α-酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因,其中所述α-酮戊二酸依赖性氧化酶为CEOXY1或CEOXY4,所述P450单加氧酶为CEP450-1、CEP450-2或CEP450-3。
在本发明一些优选实施方案中,所述出发菌为Coleophoma empetri F-11899,和/或,所述CEOXY1的氨基酸序列如SEQ ID NO:24所示,和/或,所述CEOXY4的氨基酸序列如SEQID NO:26所示,和/或,所述CEP450-1的氨基酸序列如SEQ ID NO:28所示,和/或,所述CEP450-2的氨基酸序列如SEQ ID NO:30所示,和/或,所述CEP450-3的氨基酸序列如SEQ IDNO:32所示。
在本发明一些优选实施方案中,编码所述CEOXY1的核苷酸序列如SEQ ID NO:25所示,和/或,编码所述CEOXY4的核苷酸序列如SEQ ID NO:27所示,和/或,编码所述CEP450-1的核苷酸序列如SEQ ID NO:29所示,和/或,编码所述CEP450-2的核苷酸序列如SEQ ID NO:31所示,和/或,编码所述CEP450-3的核苷酸序列如SEQ ID NO:33所示。
为解决上述技术问题,本发明提供的技术方案之二为:一种如技术方案之一所述的基因工程菌的构建方法,所述构建方法为在出发菌中使如技术方案之一中所定义的编码α-酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因失活。
在本发明一些优选实施方案中,所述失活为在所述出发菌中导入cas9***和靶向如技术方案之一中所定义的编码α-酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因的sgRNA表达盒。
在本发明一些具体实施方案中,所述导入的方法为通过农杆菌介导法导入相应的质粒。
在本发明一些具体实施方案中,所述cas9***包含编码cas9酶的基因,所述sgRNA表达盒包含能够特异性识别目的基因的N20片段。
在本发明一些具体实施方案中,所述sgRNA表达盒由5s rRNA作为启动子,引导N20片段和sgRNA的转录。
在本发明一些具体实施方案中,通过导入质粒pDHt/sk-PC导入所述cas9***;通过导入敲除质粒导入所述sgRNA表达盒。
在本发明一些具体实施方案中,所述敲除质粒还包含抗性基因表达盒,所述抗性基因表达盒为G418抗性基因表达盒,所述G418抗性基因表达盒包含trpC启动子片段、trpC终止子片段和G418抗性基因Neo片段;所述敲除质粒的骨架为pAg1-H3。
在本发明一些优选实施方案中,所述编码cas9酶的基因的核苷酸序列如SEQ IDNO:38所示;和/或,所述N20片段的核苷酸序列如SEQ ID NO:1、SEQ ID NO:2、SEQ ID NO:3、SEQ ID NO:4和/或SEQ ID NO:5所示。
为解决上述技术问题,本发明提供的技术方案之三为:一种FR901379衍生物,所述FR901379衍生物的结构如式I所示:
R1为H;R2、R4和R5独立地为H或OH;R3为C1-6烷基或H(优选为甲基);R6为H或X+为一价阳离子;
或,R3为H;R1、R2、R4和R5独立地为H或OH;R6为H或X+为一价阳离子;
或,R1、R2和R4为OH;R3为C1-6烷基;R5和R6为H;
带“*”的碳原子独立地为手性碳原子或非手性碳原子,当为手性碳原子时,独立地为R构型和/或S构型。
在某一方案中,所述X+为Na+、K+或NH4 +,例如为Na+。
在某一方案中,R3中,所述C1-6烷基为甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基;优选为甲基。
在某一方案中,所述FR901379衍生物的结构如式I-1所示:
在某一方案中,R1为H;R2为OH;R3为甲基;R4为H;R5为H;R6为OSO3Na。
在某一方案中,R1为OH;R2为OH;R3为H;R4为OH;R5为OH;R6为OSO3Na。
在某一方案中,R1为OH;R2为OH;R3为H;R4为OH;R5为H;R6为OSO3Na。
在某一方案中,R1为OH;R2为H;R3为H;R4为OH;R5为H;R6为OSO3Na。
在某一方案中,R1为H;R2为H;R3为甲基;R4为OH;R5为H;R6为OSO3Na。
在某一方案中,R1为OH;R2为OH;R3为甲基;R4为OH;R5为H;R6为H。
在某一方案中,所述FR901379衍生物为以下任一化合物:
为解决上述技术问题,本发明提供的技术方案之四为:一种制备FR901379衍生物的方法,所述方法包括在发酵培养基中培养如技术方案之一所述的基因工程菌,使其表达产生FR901379衍生物;所述FR901379衍生物为如技术方案之三所定义,或为FR901381或FR901382。
在本发明一些具体实施方案中,所述发酵培养基的pH值为6.0~7.0,和/或,所述发酵培养基包含80~120g/L甘露醇,4~6g/L棉籽饼粉,8~12g/L黄豆饼粉,3~5g/L K2HPO4和0.8~1.2g/L CaCO3;和/或,所述培养的温度为23~27℃,和/或,所述培养的转速为200~240rpm,和/或,所述培养的时间为8~12天。
在本发明一些优选实施方案中,所述发酵培养基的pH值为6.5;所述甘露醇浓度为100g/L,所述棉籽饼粉浓度为5g/L,所述黄豆饼粉浓度为10g/L,所述K2HPO4浓度为4g/L,所述CaCO3浓度为1g/L;所述温度为25℃;所述转速为220rpm;所述时间为10天。
为解决上述技术问题,本发明提供的技术方案之五为:如技术方案之一所述的基因工程菌在生产FR901379衍生物中的应用,所述FR901379衍生物如技术方案之三所定义,或所述FR901379衍生物为FR901381或FR901382。
在符合本领域常识的基础上,上述各优选条件,可任意组合,即得本发明各较佳实例。
本发明所用试剂和原料均市售可得。
本发明的积极进步效果在于:
本发明在丝状真菌Coleophoma empetri F-11899中利用CRISPR/Cas9的方法对参与FR901379合成的基因进行敲除,验证了基因的功能,获得了具有生产FR901379衍生物功能的基因工程菌。同时还获得了一系列具有生物活性的衍生物,该类衍生物具有一定的成药潜在价值。
附图说明
图1为对照菌株Ce-PC、工程菌株C.e(ΔCeoxy1)、工程菌株C.e(ΔCeoxy4)、工程菌株C.e(ΔCEp450-1)、工程菌株C.e(ΔCEp450-2)、工程菌株C.e(ΔCEp450-3)的发酵产物的HPLC图谱。
图2为对照菌株Ce-PC、工程菌株C.e(ΔCeoxy2)的HPLC图谱。
图3为对照菌株Ce-PC、工程菌株C.e(ΔCeoxy3)的HPLC图谱。
具体实施方式
下面通过实施例的方式进一步说明本发明,但并不因此将本发明限制在所述的实施例范围之中。下列实施例中未注明具体条件的实验方法,按照常规方法和条件,或按照商品说明书选择。
本发明敲除菌株的构建:
首先将含有cas9基因(SEQ ID NO:38)的质粒pDHt/sk-PC通过农杆菌介导(Agrobacterium tumefaciens-mediated transformation,AMT)的方法导入出发菌株Coleophoma empetri F-11899,获得工程菌株Ce-PC。
在质粒pAgG的基础上利用分子克隆方法构建用于基因敲除的sgRNA表达盒子,该表达盒子由5s rRNA作为启动子,引导N20和sgRNA的转录,N20为用于敲除目的基因的20bp的靶基因序列。对于不同的目的基因,设计的N20如下表1:
表1
将构建好的敲除质粒导入工程菌株Ce-PC中,挑取转化子,对转化子进行PCR验证筛选,对得到的敲除菌株进行发酵培养,HPLC检测发酵产物,LC-MS分析产物的分子量。
最后,将本专利中的所有化合物进行抗真菌活性检测。
本发明所用的菌株、质粒、试剂、仪器及HPLC检测方法:
菌株Aspergillus pachycristatus NRRL11440购自于NRRL菌种保藏中心。用于AMT的Agrobacterium tumefaciens LBA4404感受态购自唯地生物公司。质粒pAg1-H3来自于中国科学院微生物研究所。pDHt/sk-PC来自于中国科学院上海生命科学研究院植物生理生态研究所合成生物学元件与数据库研究组。
本发明中使用的DNA胶回收纯化试剂盒和质粒提取试剂盒购自上海生工,反转录试剂盒、PCR酶及所有限制性内切酶都购自Takara公司,同源重组试剂盒(ClonExpress IIOne Step Cloning Kit)购自Vazyme公司,色谱纯的乙腈购自Amethyst Chemicals公司,其他常规试剂均为国产分析纯或进口分装。
本发明中使用的恒温发酵摇床购自上海世平实验设备有限公司,1200型高效液相色谱仪购自Agilent Technologies公司。
本发明所用的培养基
1、液体LB培养基(1L)
蛋白胨10g,酵母提取物5g,NaCl 10g,蒸馏水1L;121℃灭菌20分钟。
2、固体LB培养基(1L)
蛋白胨10g,酵母提取物5g,NaCl 10g,琼脂粉20g;121℃灭菌20分钟。
3、PPY培养基(1L):高聚蛋白胨20g,酵母提取物20g,马铃薯肉汤培养基20g。
4、诱导液体培养基(IM):0.8mL K buffer,20mL MN buffer,1mL 1%CaCl2·2H2O,10mL 0.01%FeSO4·7H2O,5mL微量元素,2.5mL 20%硝酸铵,10mL 50%甘油,40mL1M MES,10mL 20%葡萄糖,加905.7mL无菌水。
培养基中所用溶液:
1%CaCl2·2H2O:称取1g CaCl2·2H2O,加水定容至100mL,使用前需灭菌。
0.01%FeSO4·7H2O:称取0.01g FeSO4·7H2O,加水定容至100mL,使用前需过滤除菌。
20%葡萄糖:称取20g葡萄糖,加水定容至100mL,使用前需灭菌。
50%甘油:量取50mL的甘油,与50mL的水混匀,使用前需灭菌。
20%硝酸铵:称取20g硝酸铵,加水定容至100mL,使用前需灭菌。
K buffer:将1.25M K2HPO4·3H2O加入1.25M K2HPO4至PH为4.8,使用前需灭菌。
MN buffer:称取3g MgSO4·7H2O和1.5g NaCl,加水定容至100mL,使用前需灭菌。
微量元素:称取10mg ZnSO4·7H2O,10mg CuSO4·5H2O,10mg H3BO3,10mg MnSO4·H2O,10mg NaMoO4·2H2O,加水定容至100mL,使用前需灭菌。
1M MES:称取10.66g MES,溶解于水中,调节pH至5.3,定容至50mL。保存于-20℃冰箱中,使用前需过滤除菌。
0.2M AS:称取785mg的AS,溶解于DMSO中,定容至20mL,避光保存于20℃冰箱中,使用前需过滤除菌。
5、诱导固体培养基:向以灭菌的含2%琼脂粉的无菌水中加0.8mL K buffer,20mLMN buffer,1mL 1%CaCl2·2H2O,10mL 0.01%FeSO4·7H2O,5mL微量元素,2.5mL 20%硝酸铵,10mL 50%甘油,40mL 1M MES,10mL 20%葡萄糖。
6、种子培养基配方(1L):
葡萄糖20g,黄豆饼粉10g,KH2PO4 2g,pH值为6.5;121℃灭菌20分钟。
7、发酵培养基配方(1L):
甘露醇100g,棉籽饼粉5g,黄豆饼粉10g,K2HPO4 4g,CaCO3 1g,pH值为6.5;121℃灭菌20分钟。
本发明中的HPLC检测方法为:
HPLC液相检测方法:
流动相:50%乙腈和50%水(含0.5%NaH2PO4);
色谱柱:C18 4.6×250nm;
流速:1mL/min;
检测波长:210nm;
柱温:30℃;
进样量:20μL。
本发明所用引物的碱基序列见下表2,其中-F表示上游引物,-R表示下游引物。
表2
实施例1CEoxy1的基因敲除及产物分析
本实施例敲除的CEoxy1的基因的氨基酸序列如SEQ ID NO:24所示,其核苷酸序列如SEQ ID NO:25所示。
1、质粒构建:
(1)pAgG及pAgG-sgRNA-CEoxy1的构建
以pAg1-H3为模板,用引物Ptrpc-F/R(本实施例使用的引物的碱基序列见表2)进行PCR得到trpC启动子片段(片段1)。以质粒pEGFP-N2为模板,用引物NeoR-F/R进行PCR得到G418抗性基因Neo片段(片段2)。以pAg1-H3为模板,用引物Ttrpc-F/R进行PCR,得到trpC终止子片段(片段3)。以PCR片段1,片段2,片段3为模板,用引物Ptrpc-F和Ttrpc-R进行重叠PCR,得到G418抗性基因表达盒,将该表达盒连接至HindIII/SpeI线性化的pAg1-H3载体上,最终得到质粒pAg1-HG。pAg1-HG利用EcoRI单切后自连得到pAgG。
以Coleophoma empetri F-11899基因组为模板,5S-F/R为引物,PCR得到5s rRNA片段。用N20-CEoxy1-F和sgRNA-R为引物,PCR得到可特异性识别CEoxy1的sgRNA片段。以5srRNA片段和sgRNA片段作为模板,用5S-F和sgRNA-R为引物进行重叠PCR,得到sgRNA表达盒。将该表达盒利用同源重组试剂盒(ClonExpress II One Step Cloning Kit)连接至BglII/EcoRI酶切处理的pAgG线性载体,得到敲除质粒pAgG-sgRNA-CEoxy1。
2、敲除菌株的构建
利用AMT,将质粒pAgG-sgRNA-CEoxy1导入Ce-PC菌株中,筛选得到工程菌株C.e(CEoxy1)。
3、工程菌株C.e(CEoxy1)的发酵
为了检测工程菌株C.e(ΔCEoxy1)的发酵产物,将其接种于20mL种子培养基中,25℃,220rpm,培养4d,按10%接种量接种到30mL发酵培养基中,25℃,220rpm,培养10天。
4、HPLC检测
利用反向HPLC(安捷伦)检测发酵产物:取2mL发酵液,加8ml丙酮充分混匀,超声震荡30min,过滤后得滤液进行检测,结果如图1所示。
结果显示:工程菌株C.e(CEoxy1)的发酵产物化合物1的分子量为1149,经分析化合物1的结构为:
5、抗真菌活性:活性结果见下表3,由结果可知,化合物1有抗真菌活性。
实施例2CEoxy4的基因敲除及产物分析
本实施例敲除的CEoxy4的基因的氨基酸序列如SEQ ID NO:26所示,其核苷酸序列如SEQ ID NO:27所示。
1、质粒构建:
(1)pAgG-sgRNA-CEoxy4的构建
以Coleophoma empetri F-11899基因组为模板,5S-F/R为引物,PCR得到5s rRNA片段。用N20-CEoxy4-F和sgRNA-R为引物,PCR得到可特异性识别CEoxy4的sgRNA片段。以5srRNA片段和sgRNA片段作为模板,用5S-F和sgRNA-R为引物进行重叠PCR,得到sgRNA表达盒。将该表达盒利用同源重组试剂盒(ClonExpress II One Step Cloning Kit)连接至BglII/EcoRI酶切处理的pAgG线性载体,得到敲除质粒pAgG-sgRNA-CEoxy4。
2、敲除菌株的构建
利用AMT,将质粒pAgG-sgRNA-CEoxy4导入Ce-PC菌株中,筛选得到工程菌株C.e(ΔCEoxy4)。
3、工程菌株C.e(ΔCEeoxy4)的发酵
为了检测工程菌株C.e(ΔCEoxy4)的发酵产物,将其接种于20mL种子培养基中,25℃,220rpm,培养4d,按10%接种量接种到30mL发酵培养基中,25℃,220rpm,培养10天。
4、HPLC检测
利用反向HPLC(安捷伦)检测发酵产物:取2mL发酵液,加8ml丙酮充分混匀,超声震荡30min,过滤后得滤液进行检测,结果如图1所示。
结果显示:工程菌株C.e(ΔCeoxy4)的发酵产物化合物2、3、4的分子量分别为1160、1144、1128,经分析化合物2的结构为:
经分析化合物3的结构为:
经分析化合物4的结构为:
5、抗真菌活性:活性结果见下表3,由结果可知,化合物2、3、4均有抗真菌活性。
实施例3CEp450-1的基因敲除及产物分析
本实施例敲除的CEp450-1的基因的氨基酸序列如SEQ ID NO:28所示,其核苷酸序列如SEQ ID NO:29所示。
1、质粒构建:
(1)pAgG-sgRNA-CEp450-1的构建
以Coleophoma empetri F-11899基因组为模板,5S-F/R为引物,PCR得到5s rRNA片段。用N20-CEp450-1-F和sgRNA-R为引物,PCR得到可特异性识别CEp450-1的sgRNA片段。以5s rRNA片段和sgRNA片段作为模板,用5S-F和sgRNA-R为引物进行重叠PCR,得到sgRNA表达盒。将该表达盒利用同源重组试剂盒(ClonExpress II One Step Cloning Kit)连接至BglII/EcoRI酶切处理的pAgG线性载体,得到敲除质粒pAgG-sgRNA-CEp450-1。
2、敲除菌株的构建
利用AMT,将质粒pAgG-sgRNA-CEp450-1导入Ce-PC菌株中,筛选得到工程菌株C.e(ΔCEp450-1)。
3、工程菌株C.e(ΔCEp450-1)的发酵
为了检测工程菌株C.e(ΔCEp450-1)的发酵产物,将其接种于20mL种子培养基中,25℃,220rpm,培养4d,按10%接种量接种到30mL发酵培养基中,25℃,220rpm,培养10天。
4、HPLC检测
利用反向HPLC(安捷伦)检测发酵产物:取2mL发酵液,加8ml丙酮充分混匀,超声震荡30min,过滤后得滤液进行检测,结果如图1所示。
结果显示:工程菌株C.e(ΔCEp450-1)的发酵产物分别为FR901381和FR901382,分子量分别为1158、1142,经分析FR901381的结构为:
经分析FR901382的结构为:
5、抗真菌活性:活性结果见下表3,由结果可知,FR901381和FR901382均有抗真菌活性。
实施例4CEp450-2的基因敲除及产物分析
本实施例敲除的CEp450-2的基因的氨基酸序列如SEQ ID NO:30所示,其核苷酸序列如SEQ ID NO:31所示。
1、质粒构建:
(1)pAgG-sgRNA-CEp450-2的构建
以Coleophoma empetri F-11899基因组为模板,5S-F/R为引物,PCR得到5s rRNA片段。用N20-CEp450-2-F和sgRNA-R为引物,PCR得到可特异性识别CEp450-2的sgRNA片段。以5s rRNA片段和sgRNA片段作为模板,用5S-F和sgRNA-R为引物进行重叠PCR,得到sgRNA表达盒。将该表达盒利用同源重组试剂盒(ClonExpress II One Step Cloning Kit)连接至BglII/EcoRI酶切处理的pAgG线性载体,得到敲除质粒pAgG-sgRNA-CEp450-2。
2、敲除菌株的构建
利用AMT,将质粒pAgG-sgRNA-CEp450-2导入Ce-PC菌株中,筛选得到工程菌株C.e(ΔCEp450-2)。
3、工程菌株C.e(ΔCEp450-2)的发酵
为了检测工程菌株C.e(ΔCEp450-2)的发酵产物,将其接种于20mL种子培养基中,25℃,220rpm,培养4d,按10%接种量接种到30mL发酵培养基中,25℃,220rpm,培养10天。
4、HPLC检测
利用反向HPLC(安捷伦)检测发酵产物:取2mL发酵液,加8ml丙酮充分混匀,超声震荡30min,过滤后得滤液进行检测,结果如图1所示。
结果显示:工程菌株C.e(ΔCEp450-2)的发酵产物化合物5分子量为1126,经分析化合物5的结构为:
5、抗真菌活性:活性结果见下表3,由结果可知,化合物5有抗真菌活性。
实施例5CEp450-3的基因敲除及产物分析
本实施例敲除的CEp450-3的基因的氨基酸序列如SEQ ID NO:32所示,其核苷酸序列如SEQ ID NO:33所示。
1、质粒构建:
(1)pAgG-sgRNA-CEp450-3的构建
以Coleophoma empetri F-11899基因组为模板,5S-F/R为引物,PCR得到5s rRNA片段。用N20-CEp450-3-F和sgRNA-R为引物,PCR得到可特异性识别CEp450-3的sgRNA片段。以5s rRNA片段和sgRNA片段作为模板,用5S-F和sgRNA-R为引物进行重叠PCR,得到sgRNA表达盒。将该表达盒利用同源重组试剂盒(ClonExpress II One Step Cloning Kit)连接至BglII/EcoRI酶切处理的pAgG线性载体,得到敲除质粒pAgG-sgRNA-CEp450-3。
2、敲除菌株的构建
利用AMT,将质粒pAgG-sgRNA-CEp450-3导入Ce-PC菌株中,筛选得到工程菌株C.e(ΔCEp450-3)。
3、工程菌株C.e(ΔCEp450-3)的发酵
为了检测工程菌株C.e(ΔCEp450-3)的发酵产物,将其接种于20mL种子培养基中,25℃,220rpm,培养4天,按10%接种量接种到30mL发酵培养基中,25℃,220rpm,培养10天。
4、HPLC检测
利用反向HPLC(安捷伦)检测发酵产物:取2mL发酵液,加8ml丙酮充分混匀,超声震荡30min,过滤后得滤液进行检测,结果如图1所示。
结果显示:工程菌株C.e(ΔCEp450-3)的发酵产物化合物6的分子量为1126,经分析化合物6的结构为:
5、抗真菌活性:化合物6的抗菌活性结果见表3,由结果可知,化合物6有抗真菌活性。
表3抑菌活性检测结果
本发明所有涉及到的化合物结构通式如下,其中各化合物的基团R1~R6汇总如表4所示。
表4
对比例1CEoxy2和CEoxy3的基因敲除及产物分析
本对比例敲除的CEoxy2的基因的氨基酸序列如SEQ ID NO:34所示,其核苷酸序列如SEQ ID NO:35所示;敲除的CEoxy3的基因的氨基酸序列如SEQ ID NO:36所示,其核苷酸序列如SEQ ID NO:37所示。
1、质粒构建:
(1)pAgG-sgRNA-CEoxy2和pAgG-sgRNA-CEoxy3的构建
以Coleophoma empetri F-11899基因组为模板,5S-F/R为引物,PCR得到5s rRNA片段。用N20-CEoxy2-F和sgRNA-R为引物,PCR得到可特异性识别CEoxy2的sgRNA片段。以5srRNA片段和sgRNA片段作为模板,用5S-F和sgRNA-R为引物进行重叠PCR,得到sgRNA表达盒。将该表达盒利用同源重组试剂盒(ClonExpress II One Step Cloning Kit)连接至BglII/EcoRI酶切处理的pAgG线性载体,得到敲除质粒pAgG-sgRNA-CEoxy2。同样的方法获得敲除质粒pAgG-sgRNA-CEoxy3。
2、敲除菌株的构建
利用AMT,将质粒pAgG-sgRNA-CEoxy2导入Ce-PC菌株中,筛选得到工程菌株C.e(ΔCEoxy2)。将质粒pAgG-sgRNA-CEoxy3导入Ce-PC菌株中,筛选得到工程菌株C.e(ΔCEoxy3)。
3、工程菌株的发酵
为了检测工程菌株C.e(ΔCEoxy2)和C.e(ΔCEoxy3)的发酵产物,将其接种于20mL种子培养基中,25℃,220rpm,培养4d,按10%接种量接种到30mL发酵培养基中,25℃,220rpm,培养10天。
4、HPLC检测
利用反向HPLC(安捷伦)检测发酵产物:取2mL发酵液,加8ml丙酮充分混匀,超声震荡30min,过滤后得滤液进行检测。
结果显示:如图2和图3所示,发酵产物中无FR901379及结构类似物的产生。
SEQUENCE LISTING
<110> 上海医药工业研究院有限公司
中国医药工业研究总院有限公司
<120> 一种生产FR901379衍生物的基因工程菌及其应用
<130> P22010845C
<160> 38
<170> PatentIn version 3.5
<210> 1
<211> 20
<212> DNA
<213> Artificial Sequence
<220>
<223> CEoxy1 N20
<400> 1
tccacaggac aggacgcttc 20
<210> 2
<211> 20
<212> DNA
<213> Artificial Sequence
<220>
<223> CEoxy4 N20
<400> 2
tctcgcgaga ggagatatcg 20
<210> 3
<211> 20
<212> DNA
<213> Artificial Sequence
<220>
<223> CEp450-1 N20
<400> 3
tcgcaggccc agaaatctgt 20
<210> 4
<211> 20
<212> DNA
<213> Artificial Sequence
<220>
<223> CEp450-2 N20
<400> 4
tcggcgtaac agctcctgca 20
<210> 5
<211> 20
<212> DNA
<213> Artificial Sequence
<220>
<223> CEp450-3 N20
<400> 5
aagttctgcg caagactaga 20
<210> 6
<211> 20
<212> DNA
<213> Artificial Sequence
<220>
<223> Ceoxy2 N20
<400> 6
tcgatgtgga ttgggtgctg 20
<210> 7
<211> 20
<212> DNA
<213> Artificial Sequence
<220>
<223> Ceoxy3 N20
<400> 7
gaccgcaaaa gtgatacagt 20
<210> 8
<211> 34
<212> DNA
<213> Artificial Sequence
<220>
<223> Ptrpc-F
<400> 8
acccaagctt gggaatcgat gatcaggcct cgac 34
<210> 9
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> Ptrpc-R
<400> 9
aatccatctt gttcaatcat ttggatgctt gggtagaata 40
<210> 10
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> NeoR-F
<400> 10
tattctaccc aagcatccaa atgattgaac aagatggatt 40
<210> 11
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> NeoR-R
<400> 11
gatcccggtc ggcatctact tcagaagaac tcgtcaagaa 40
<210> 12
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> Ttrpc-F
<400> 12
ttcttgacga gttcttctga agtagatgcc gaccgggatc 40
<210> 13
<211> 34
<212> DNA
<213> Artificial Sequence
<220>
<223> Ttrpc-R
<400> 13
ctggactagt ccttcgtccg gcgtagagga tcct 34
<210> 14
<211> 46
<212> DNA
<213> Artificial Sequence
<220>
<223> sgRNA-R
<400> 14
gactagtcgg gggatcctct agatcttctg caggtcgact ctagag 46
<210> 15
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> 5S-F
<400> 15
gttgtaaaac gacggccagt gaaacgttgg acgcgccgct 40
<210> 16
<211> 24
<212> DNA
<213> Artificial Sequence
<220>
<223> 5S-R
<400> 16
ggtgtttcgt cctttcatac aaca 24
<210> 17
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> N20-CEoxy4-N20-F
<400> 17
tctcgcgaga ggagatatcg gttttagagc tagaaatagc 40
<210> 18
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> N20-CEoxy1-N20-F
<400> 18
tccacaggac aggacgcttc gttttagagc tagaaatagc 40
<210> 19
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> N20-CEp450-1-N20-F
<400> 19
tcgcaggccc agaaatctgt gttttagagc tagaaatagc 40
<210> 20
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> N20-CEp450-2-N20-F
<400> 20
tcggcgtaac agctcctgca gttttagagc tagaaatagc 40
<210> 21
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> N20-CEp450-3-N20-F
<400> 21
aagttctgcg caagactaga gttttagagc tagaaatagc 40
<210> 22
<211> 59
<212> DNA
<213> Artificial Sequence
<220>
<223> N20-CEoxy2-F
<400> 22
tatgaaagga cgaaacacct cgatgtggat tgggtgctgg ttttagagct agaaatagc 59
<210> 23
<211> 59
<212> DNA
<213> Artificial Sequence
<220>
<223> N20-CEoxy3-F
<400> 23
tatgaaagga cgaaacaccg accgcaaaag tgatacagtg ttttagagct agaaatagc 59
<210> 24
<211> 321
<212> PRT
<213> Artificial Sequence
<220>
<223> CEOXY1氨基酸序列
<400> 24
Met Tyr Ser Ile Ser Phe Thr Gly Leu Leu Glu Gly Asn Ala Lys Asp
1 5 10 15
Val Gln Thr Leu Ala Glu Ala Ala Thr Thr Gln Gly Phe Phe Asn Leu
20 25 30
Glu Leu Asp Cys Thr Asp Ala Lys Val Leu Gln Glu Asp Val Lys Phe
35 40 45
Leu Glu Ser Phe Ala Lys Asp Ile Leu Asp Ser Pro Glu Asp Ile Lys
50 55 60
Glu Ala Tyr His Phe His Arg Thr Gly Arg Phe Arg Thr Thr Gly Phe
65 70 75 80
Lys Pro Leu Gly Ile Glu Glu Gly Ala Lys Gln Gly Arg Pro Asp Gly
85 90 95
Phe Glu Leu Phe Met Leu Pro Ser Lys Glu Leu Leu Leu Ser Glu Phe
100 105 110
Lys Lys Glu Leu Asn Cys Pro Pro Leu Val Met Ser Asn Ala Asp Arg
115 120 125
Leu Thr Asp Ser Leu Arg Asp Tyr Glu Arg Val Ala Gln Met Ile Leu
130 135 140
Gln Arg Leu Thr Glu Gly Leu Gly Leu Gly Asn Glu Met Leu His Ala
145 150 155 160
His Asp Pro Ser Leu Pro Ser Val Thr Asn Met Gly Phe Ile Lys Tyr
165 170 175
Pro Pro Gln Pro Gln Glu Ser Lys Asn Phe Gly His Ile Ala His Thr
180 185 190
Asp Val Gly Ser Leu Thr Ile Leu Ser Ala Thr Glu Arg Gly Leu Gln
195 200 205
Ala Leu Asp Ser Lys Thr Lys Asp Trp Val Trp Val Glu Pro Ser Asp
210 215 220
Gln Val Leu Phe Val Gln Leu Gly Asp Ser Leu Lys Phe Leu Ser Gln
225 230 235 240
Gly Lys Ile Leu Pro Ser Leu His Arg Val Val Pro Ser Asp Val Ala
245 250 255
Pro Gln Ala Thr Lys Tyr Thr Ile Ala Tyr Phe Leu Arg Pro Asn Glu
260 265 270
Glu Val Glu Ile Thr Ala Asp Asp Gly Lys Val Trp Leu Tyr Lys Asp
275 280 285
Tyr His Cys Arg Lys Phe Asp Ala Phe Ala Arg Pro Leu Gly Tyr Arg
290 295 300
Pro Asp Gly Glu Glu Ser Leu Ile Ser Leu Arg Asp Tyr Ala Arg Val
305 310 315 320
Glu
<210> 25
<211> 1067
<212> DNA
<213> Artificial Sequence
<220>
<223> CEoxy1 核苷酸序列(含内含子)
<400> 25
atgtatagca tatccttcac cggccttctt gagggcaatg ccaaagatgt tcaaactctg 60
gcagaagcgg caactactca aggattcttc aacttagagc tcgattgcac agatgcgaaa 120
gtattgcaag aagatgtgaa gttccttgaa tcatttgcaa aggacattct tgatagtccc 180
gaggatataa aggaagctta ccatttccac aggacaggac gcttccggac tacagggtat 240
ggtaaaaatc gatcatgttg aaattaagct aatgtttaat actaggttca agcctctcgg 300
aattgaggaa ggagcaaaac aaggaagacc tgatggattt gagctcttca tggtaggttt 360
aacgaaagga aaagtatgcg tggttgctta ccttgtactt gtagttgcct tcaaaggaac 420
ttctgctttc ggagttcaaa aaggagctta attgtccccc tttggttatg tcgaatgccg 480
acagactcac cgacagcctc agggattacg aacgagtggc tcagatgatc ttgcaacgtt 540
tgacagaagg cctcggactc ggtaatgaaa tgctgcatgc ccatgatccc tctttacctt 600
ctgtcacgaa tatgggcttc ataaagtatc cacctcaacc ccaggagtcc aagaattttg 660
gccatattgc tcatacggat gttggaagct tgaccatcct ttctgcaact gagagaggac 720
tacaagctct cgatagcaaa actaaggatt gggtatgggt tgagcccagc gatcaggttc 780
tgttcgtaca gctaggagat tcacttaaat tcctctccca gggcaagatc ttgccctctc 840
ttcatagggt cgtacctagc gatgtcgccc ctcaggcaac aaagtacaca attgcatact 900
ttttacgccc caacgaggag gttgaaatca ctgctgatga cggaaaagtt tggctttata 960
aggattatca ctgtagaaag ttcgacgctt ttgcaagacc attgggctat agaccagacg 1020
gggaagagtc acttatatca ttgcgtgact acgcaagggt ggagtag 1067
<210> 26
<211> 332
<212> PRT
<213> Artificial Sequence
<220>
<223> CEOXY4氨基酸序列
<400> 26
Met Glu Ile Lys Thr Leu Asp Phe Ser Lys Phe His Ala Gly Thr Glu
1 5 10 15
Ala Glu Arg Tyr Glu Phe Ser Lys Leu Leu Leu Thr Gly Phe Ala Ser
20 25 30
Thr Gly Phe Val Lys Leu Ile Asn His Gly Phe Ser Arg Glu Glu Ile
35 40 45
Ser Arg Thr Phe Asp Glu Asn Arg Arg Phe Phe Glu Leu Thr Asp Ser
50 55 60
Val Lys Ala Pro Ile Ala Asn Glu Asp Gly Pro Lys Pro Gln Arg Gly
65 70 75 80
Trp Ser Ser Val Gly Ala Glu Lys Thr Gly Leu Leu Asn Thr Gly Gly
85 90 95
Lys Ile Asn Leu Thr Lys Pro Glu Met Glu Asp Arg Gln Asp Ala Lys
100 105 110
Glu His Phe Asp Ile Gly Pro Ser Gly Asp Thr Glu Phe Pro Asn Lys
115 120 125
Trp Pro Asn Asp Lys Leu Ile Pro Gly Phe Arg Pro Trp Leu Glu Ser
130 135 140
Tyr Phe Asp Arg Ser Gln Gln Ile Thr Leu Glu Leu Met Glu Ala Leu
145 150 155 160
Glu Ile Ala Met Gln Leu Pro Lys Gly Ala Phe Val Gln Lys Cys Gln
165 170 175
Gly His Ala Ser Glu Leu Arg Leu Asn His Tyr Pro Gly Ile Ser Val
180 185 190
Lys Thr Leu Glu Glu Gly Gln Thr Ser Arg Ile Trp Pro His Thr Asp
195 200 205
Phe Gly Ile Ile Thr Leu Leu Ser Gln Asp Asp Val Gly Gly Leu Glu
210 215 220
Ile Lys Asp Lys Asp His Pro Thr Asn Phe Ile Pro Val Pro Arg Glu
225 230 235 240
Asp Pro Ala Glu Leu Val Val Asn Ile Gly Asp Thr Leu Glu Arg Trp
245 250 255
Thr Asn Gly Ile Leu Gln Ala Gly Leu His Gln Val Thr Thr Pro Arg
260 265 270
Glu Met Leu Asn Arg Cys Asp Glu Asn Leu Arg Pro Arg Arg Ser Ile
275 280 285
Ala Phe Phe Leu Lys Ala His Arg Gln Met Ser Val Gly Pro Leu Ser
290 295 300
Gln Phe Val Ala Glu Lys Thr Pro Ala Lys Tyr Glu Asp Met Thr Ala
305 310 315 320
Leu Ala Tyr Gln Gln Arg Arg Thr Ala Ile Val Tyr
325 330
<210> 27
<211> 1106
<212> DNA
<213> Artificial Sequence
<220>
<223> CEoxy4 核苷酸序列(含内含子)
<400> 27
atggagatta aaacccttga cttttccaag ttccatgccg gaaccgaggc tgaacgctac 60
gagttctcaa aactcctatt aactggcttc gcaagcacag gcttcgtgaa gctcattaat 120
cacggcttct cgcgagagga gatatcgcgg acctttgatg aggtatgtcc gtagttaact 180
agtagcggtt caaaacactg actgctacag aaccgacgct ttttcgaact taccgactca 240
gttaaagcac caattgctaa tgaagatggc ccgaaacctc aacgaggatg gagttcagtt 300
ggagctgaga agactggcct tctgaacacc ggcggaaaga tcaatctcac caaaccagag 360
atggaagacc gtcaagatgc aaaggtacag caagctggcg cccacagatt tagtatcacc 420
caagtatcta attgtatctt caggaacatt tcgatattgg tccctcaggc gacaccgaat 480
tccctaacaa atggcctaat gataaattga ttcccggctt ccgcccatgg ctcgagtcgt 540
acttcgacag gagccagcag ataactctcg aattaatgga agctttagag atcgcaatgc 600
agctcccgaa aggtgctttc gttcagaagt gtcaaggaca tgctagtgaa ctccgtctta 660
atcactaccc aggaatatcc gtcaagactc tggaagaagg ccaaacgagt cgtatctggc 720
ctcacaccga ttttggcatc atcaccctcc tctcccagga cgatgtagga ggactcgaaa 780
tcaaagataa ggaccaccca accaatttta tacctgtacc aagagaggat ccagctgaat 840
tggtcgtcaa catcggtgat acccttgaga ggtggacgaa tggtattctg caggctggac 900
tacaccaagt taccacaccg agggagatgt tgaaccggtg tgacgagaac ttgcggccta 960
gaaggtcgat cgctttcttc ctcaaggctc acaggcaaat gtcagtgggc ccattgtctc 1020
agtttgtggc agagaagacg cccgccaagt atgaggacat gacagccctg gcgtatcagc 1080
agcggaggac ggcgatagtc tactaa 1106
<210> 28
<211> 546
<212> PRT
<213> Artificial Sequence
<220>
<223> CEP450-1氨基酸序列
<400> 28
Met Leu Ser Asp Thr Thr Ala Arg Ile Glu Arg Ile Ile Ser Glu Gln
1 5 10 15
Thr Leu Phe Ser Ala Val Leu Ser Leu Phe Met Ile Gly Leu Met Ala
20 25 30
His Leu Val Leu Ala Arg Phe Ser Ile His Asn Gln Phe Trp Ser Ala
35 40 45
Gln Val Trp Thr Gly Val Arg Ala Glu Trp Phe Pro Lys Ile Arg Ala
50 55 60
Lys Phe Arg Thr Ile Gly Gly Ile Arg Gln Met Leu Ser Asp Gly Tyr
65 70 75 80
Lys Cys Phe Ser Lys Gln Glu Arg Ala Phe Val Leu Pro Met Leu Gly
85 90 95
Glu Lys Pro Trp Leu Val Leu Pro Pro Ser Ser Ile Pro Glu Leu Leu
100 105 110
Ala Lys Ser Asp Ser Glu Val Asp Met Arg Ile Val His Glu Gln Gln
115 120 125
Leu Gln His Glu Tyr Thr Gln Gly Ala Leu Gly Arg His Val Val Asp
130 135 140
Val Pro Ile Gln Tyr Asp Val Ile His Arg Gln Leu Asn Arg Lys Leu
145 150 155 160
Pro His Leu Ile Asp Pro Phe Asn Asp Glu Phe Asp Lys Ser Phe Arg
165 170 175
Lys Tyr Trp Gly Thr Asp Ala Ser Tyr Thr Asp Val Lys Val Ser Ala
180 185 190
Thr Cys Glu Lys Ile Ile Ala Gln Val Ala Asn Arg Ile Phe Ala Gly
195 200 205
Pro Glu Ile Cys Arg Asn Glu Asp Phe Leu Glu His Ser Arg Leu Tyr
210 215 220
Ser Ala Gly Val Gly Arg Cys Ala Ile Ile Leu Arg Met Leu Pro Gln
225 230 235 240
Val Ile Arg Ser Leu Val Ala Pro Leu Val Thr Tyr Pro Asn Arg Lys
245 250 255
His His Asp Val Cys Leu Arg Val Cys Leu Pro Val Val Arg Asp Arg
260 265 270
Leu Gln Arg Thr Ser Glu Lys Arg Gly Asn Leu Gln Ser Glu Trp Glu
275 280 285
Pro Pro Val Asp Met Leu Gln Trp Ile Ile Glu Glu Ala Phe Asn Arg
290 295 300
Asn Glu Pro Lys Glu Leu Asp Ala His Leu Ile Thr Gln Arg Ile Leu
305 310 315 320
Lys Leu Asn Phe Val Ser Ile Glu Thr Ile His Met Ser Met Thr His
325 330 335
Ala Ile Leu Asp Leu Tyr Arg Ser Pro His Ser Glu Arg Phe Val Ala
340 345 350
Gly Leu Arg Gln Glu Cys Asp Arg Val Leu Glu Ala Asn Asn Gly Gln
355 360 365
Trp Thr Lys Ser Gly Leu Asp Asp Leu Leu Cys Ile Asp Ser Thr Ile
370 375 380
Arg Glu Ser Met Arg Tyr Ser Asn Val Gly Tyr Ile Ala Leu Thr Arg
385 390 395 400
Met Val Val Asp Pro His Gly Thr Gln Phe His Ala Asn Gly Lys Gly
405 410 415
Asn Ser Ser Pro Met Ser Ile Pro Ser Gly Ile Arg Val Cys Val Pro
420 425 430
Ala His Ala Ile His Arg Asp Pro Glu Phe Tyr Ser Ser Pro His Glu
435 440 445
Phe Gln Ala Phe Arg Phe Ala Glu Ala Tyr Glu Lys Asn Arg Asn Ile
450 455 460
Gly Asn Glu Ser Tyr Glu Ala Lys Ile Ser Ile Val Thr Thr Thr Asp
465 470 475 480
Lys Phe Leu Pro Phe Gly His Gly Arg His Ala Cys Pro Gly Arg Phe
485 490 495
Phe Ala Ala Gln Met Met Lys Leu Met Leu Val Tyr Leu Val Gln Asn
500 505 510
Tyr Asp Val Glu Lys Leu Ser Thr Gly Val Glu Asn Lys Val Thr Val
515 520 525
Gly Thr Ala Lys Pro Asp Ser Asn Leu Ser Leu Arg Val Arg Arg Arg
530 535 540
Thr Glu
545
<210> 29
<211> 1758
<212> DNA
<213> Artificial Sequence
<220>
<223> CEp450-1 核苷酸序列(含内含子)
<400> 29
atgctttcag acacgacggc tcgcatagag cgcatcatta gcgaacagac tttattcagc 60
gctgtactca gtttgtttat gataggcctc atggctcatc tcgtgcttgc acgcttctcg 120
atacataacc aattctggag tgctcaagta tggacaggag ttcgtgcaga atggtttccc 180
aagataagag caaaattccg caccattggc ggtatacgcc aaatgttaag cgatggctat 240
aaatgcgtaa gaatatggga catatgagaa tattcacggc accatagcta acgagggata 300
gttttcaaaa caggagagag catttgtttt gcccatgctc ggcgagaaac cgtggctcgt 360
gctacctcct tccagcattc ctgagcttct tgcaaagtct gattcagagg ttgatatgcg 420
catagtccac gagcaacagc tgcaacatga gtatacgcaa ggcgccctcg gtcgccatgt 480
tgtcgacgtg cccattcaat acgatgttat ccatcgtcaa ttgaatcgaa agcttcctca 540
tttgatagac ccctttaatg atgagtttga taaaagcttc agaaaatact ggggcactga 600
tgcatcttat acagatgtaa aagtctcagc aacatgcgaa aagataatcg ctcaagttgc 660
aaaccgaatt ttcgcaggcc cagaaatctg tcggaatgag gatttcttgg aacactctag 720
gctctattca gcaggagtag ggaggtgtgc aatcatccta cgtatgcttc cacaggtaat 780
acgatcatta gttgcaccgc ttgttacata cccaaaccgc aaacaccacg atgtttgctt 840
gagagtctgc ctcccagttg taagagacag gctacaacga acctctgaga agagaggcaa 900
tcttcaatct gagtgggaac cgccggtaag tcacttagct aaattcttca tccattaaca 960
ggataagtgg actgacccaa gatttaggtg gatatgcttc aatggattat cgaagaagct 1020
tttaatcgca atgaaccaaa agagcttgat gctcacctga tcactcaacg gatacttaag 1080
cttaactttg tctccatcga aactattcac atgtctatga cccatgccat tctcgatctt 1140
taccgctcac ctcattccga gagatttgta gctggccttc gtcaagaatg tgatcgcgta 1200
cttgaagcga ataatggcca atggaccaag agcgggctcg atgacctctt gtgcattgac 1260
tcgacaatcc gcgagtcgat gagatactcg aacgttggat atatagcact gactcgaatg 1320
gttgtcgacc cgcatgggac ccaatttcat gctaatggca aaggcaacag cagtccaatg 1380
tccatacctt ctggcatccg agtctgcgtg cccgcccatg caatccacag agaccctgag 1440
ttttattctt ccccacatga atttcaagcc ttccgctttg ctgaagctta tgaaaagaat 1500
agaaacatag gaaacgaatc ttacgaggcc aagatatcta tcgtcaccac gacagataaa 1560
tttctgccct tcggccacgg ccgccacgca tgcccaggcc gcttttttgc cgctcagatg 1620
atgaagctaa tgctggttta cttggtgcaa aattacgacg tggaaaagct atccacagga 1680
gtagaaaaca aagtcacggt agggaccgcg aagcctgaca gtaatttgag tttaagagta 1740
agaaggcgga cggaatag 1758
<210> 30
<211> 526
<212> PRT
<213> Artificial Sequence
<220>
<223> CEP450-2氨基酸序列
<400> 30
Met Ile Ser Ala Val Val Pro Ile Ile Thr Ser Thr Asn Leu Val Phe
1 5 10 15
Tyr Gly Ala Thr Gly Leu Val Leu Phe Ala Ile Leu Ala Tyr Ser Leu
20 25 30
Asn Arg Leu Thr Thr Trp Glu Tyr Ser Ile Pro Asn Glu Val Gln Trp
35 40 45
Ile Asp Arg Arg Lys Glu Ser Phe Ser Tyr Leu Arg Ala Lys Ala Arg
50 55 60
Ser Leu Val Arg Asn Lys Glu Asn Val Leu Glu Ala Tyr Phe Lys Phe
65 70 75 80
Asn Lys Leu Gly Asn Ala Ala Ala Cys Ala Val Ala Phe Gly Arg Pro
85 90 95
Leu Leu Leu Leu Pro Pro Thr Phe Ile Arg Trp Ile Val Asp Gln Pro
100 105 110
Glu Ser Thr Ile Ser Leu Asp Pro Ile His Asp Asp Phe His Ala Phe
115 120 125
Val Gly Asp Gly Leu Ile Gly Asp His Thr Val Gln Glu Leu Leu Arg
130 135 140
Arg Glu Leu Thr Leu Asn Leu Asp Lys Leu Thr Pro Met Ile Asn Glu
145 150 155 160
Glu Ile Val Ser Ala Leu Asp Asp Val Leu Gly Asn Ser Thr Glu Trp
165 170 175
Lys Thr Thr Ser Leu Ala Asp Asp Leu Lys Thr Ile Ile Ala Arg Thr
180 185 190
Ser Asn Arg Val Phe Met Gly Lys Asp Leu Ser Gln Asn Glu Asp Tyr
195 200 205
Ile Asn Thr Ala Lys Gly Leu Ala Met Val Val Met Pro Glu Thr Val
210 215 220
Leu Gln Asp Leu Val Pro Gln Ile Leu Lys Gly Pro Leu Ser Lys Ile
225 230 235 240
Thr Arg Val Phe Asn Asn Ile Tyr Ala Met Lys Arg Ile Thr Ser His
245 250 255
Leu Leu Pro Val Val Arg Gln Arg Tyr Ile Asp Val Lys Asn Val Phe
260 265 270
Asp Gly Ser Gly Asp Lys Glu Gln Leu Pro Asp Asn Leu Leu Thr Trp
275 280 285
Met Val Gln Lys Ser Ile Arg Arg Gly Glu Ser Thr Ala Asn Ile Asp
290 295 300
Lys Val Leu Val Ala Arg Ile Gly Met Val Asn Leu Ala Ala Ile Glu
305 310 315 320
Thr Thr Thr Ala Ala Met Thr Lys Ser Ile Leu Asp Leu Val Thr Val
325 330 335
Gly Val Glu Gly Gly Phe Leu Glu Ala Val Gln Glu Glu Ala Leu Ala
340 345 350
Val Leu Glu Gly Cys Asn Tyr Gln Pro Glu Lys Ser Asp Val Ser Lys
355 360 365
Leu Asn Phe Thr Glu Asn Ala Ile Lys Glu Ser Leu Arg Leu Gln Val
370 375 380
Ala Phe Pro Gly Leu Met Arg Gln Val Val Ser Pro Lys Gly Val Thr
385 390 395 400
Leu Asp Asn Gly Leu His Val Pro Tyr Gly Thr Arg Val Gly Val Ser
405 410 415
Ala Ala Gly Ile His Val Asp Asp Ser Val Tyr Glu Asn Ala Thr Thr
420 425 430
Tyr Asn Pro Gly Arg Phe Met Val Ile Asp Leu Asp Ala Arg Gly Lys
435 440 445
Pro Asn Pro Leu Trp Lys Gly Thr Glu Asn Tyr Leu Ala Phe Gly Leu
450 455 460
Gly Arg Arg Ser Cys Pro Gly Arg Trp Tyr Val Thr Asp Gln Leu Lys
465 470 475 480
Leu Thr Leu Ala His Ile Phe Ser Lys Tyr Glu Ile Lys Phe Glu Lys
485 490 495
Ala Ala Lys Lys Thr Ser Ala Leu Arg Lys Ile Leu Pro Gly Ala Pro
500 505 510
Gln Asp His Val Met Ile Arg Arg Arg Ser Lys Val Ala Leu
515 520 525
<210> 31
<211> 1710
<212> DNA
<213> Artificial Sequence
<220>
<223> CEp450-2 核苷酸序列(含内含子)
<400> 31
atggttccat caatgatctc ggcagtggtc ccaataatca cctccacaaa tctggttttt 60
tatggagcaa ctggacttgt cctatttgct atcctcgcct actcacttaa cagattgaca 120
acttgggaat actcgatccc aaacgaagta caatggattg atcgtcgcaa agagtctttc 180
tcttatcttc gcgcaaaagc ccgatcgctt gttagaaaca aagaaaatgt gcttgaagct 240
tatttcaagg tctgtttaat tccaaacccg cttcgaagtt ggagaactca tttgcctaca 300
gttcaacaaa cttggtaatg cagcagcatg tgcggttgct ttcggtcgtc cattgttgct 360
tctgccgcct actttcatcc gctggattgt tgatcaacct gaatctacca tcagtttgga 420
tccgatacac gatgacttcc atgcatttgt tggagatggt ctgatcggtg atcataccgt 480
gcaggagctg ttacgccgag agttgactct taacctggac aagttgacgc ctatgatcaa 540
cgaagagatt gtttccgctt tagatgacgt attgggaaac tctactgaat ggaaaaccac 600
ttctcttgct gatgatttga aaacaatcat tgcgcggacc tctaacagag tatttatggg 660
caaagactta agtaaattgc tcctattccg cactcaaaac tgttcttatt ccattttcta 720
acacgtcata cctcaggcca aaacgaagac tacatcaaca ctgccaaagg gttggcaatg 780
gttgttatgc cagaaaccgt gctccaagat ctcgttccac aaattctgaa aggaccactt 840
tcaaagataa ctagagtgtt caacaacatc tatgcgatga aaagaatcac gtcacatttg 900
cttcctgtag taaggcaacg gtatattgat gttaagaacg tattcgatgg ttctggagac 960
aaagaacagc ttcctgacaa cttgctgaca tggatggtgc aaaagtcaat tcgtcgagga 1020
gagtctacag caaatatcga taaagtattg gtagcgcgta tcggaatggt taacctggca 1080
gctatcgaaa ctaccactgc tgccatgact aaaagcatcc tagacttggt cactgtgggt 1140
gttgaaggag gcttcctgga agctgttcag gaagaagcat tggccgtgtt ggaaggatgc 1200
aactatcaac cagaaaagag tgatgtttcg aaattgaatt tcaccgaaaa tgcaatcaag 1260
gagtcactcc gccttcaagt cgcctttcca ggtctcatgc gccaagttgt cagcccaaaa 1320
ggtgttacgc tagacaatgg tctacacgtg ccttacggta cccgtgttgg tgtatctgca 1380
gctggaatcc atgttgacga ctcggtctat gaaaacgcca cgacctacaa tcctggcaga 1440
ttcatggtca tagatttaga cgctcgaggc aaacctaatc cgttatggaa aggtactgag 1500
aactacctag cctttggcct tgggagacga tcgtgtcccg gccggtggta tgtgaccgat 1560
cagttaaaac tcacacttgc ccatatcttc tcgaagtacg agattaaatt tgagaaggct 1620
gcaaagaaga caagtgcgct aagaaaaatc ctacctggtg ctcctcaaga tcacgttatg 1680
attcgacgta gatcgaaagt agccctgtga 1710
<210> 32
<211> 500
<212> PRT
<213> Artificial Sequence
<220>
<223> CEP450-3氨基酸序列
<400> 32
Met Ile Asn Leu Ala Ser Pro Leu Phe Ala Thr Thr Ala Val Leu Val
1 5 10 15
Trp Leu Ser Ser Leu Ile Ile Tyr Arg Leu Tyr Leu Ser Pro Leu Ser
20 25 30
Arg Phe Pro Gly Pro Lys Leu Ala Ala Leu Thr Gly Trp Tyr Glu Thr
35 40 45
Tyr Phe Asp Leu Phe Lys Arg Gly Arg Tyr Trp Ile Glu Ile Glu Arg
50 55 60
Met His Glu Val Tyr Gly Pro Ile Ile Arg Ile Asn Pro Asn Glu Leu
65 70 75 80
His Val Asn Asp Pro Glu Trp Asn Glu Pro Tyr Lys Ile Ser Gly Arg
85 90 95
Val Asp Lys Tyr Asp Trp Tyr Tyr Thr Phe Val Gly Ser Ser Gly Ser
100 105 110
Ser Ser Ala Phe Gly Thr Ile Asp His Asp Val His Arg Gly Arg Arg
115 120 125
Lys Ala Gln Gln Gly Tyr Phe Thr Thr Asp Ala Ile Thr Arg Phe Glu
130 135 140
Pro His Leu Glu Thr Leu Thr Ala Lys Phe Cys Ala Arg Leu Asp Gly
145 150 155 160
Phe Lys Gly Thr Gly Lys His Val Asn Leu Ser Asp Ala Phe Arg Ser
165 170 175
Ile Ala Val Asp Val Ala Ala Met Phe Thr Leu Asn Gln Ser Tyr Gly
180 185 190
Phe Ile Asp Asp Pro Asp Phe Lys Ala Glu Val His Gln Gly Ile Arg
195 200 205
Ala Phe Pro Asp Ile Gly Val Leu Asn Arg His Phe Thr Gly Leu Phe
210 215 220
Val Val Leu Glu Ser Ile His Arg Trp Val Leu Ser Val Ile Asn Pro
225 230 235 240
Ser Glu Glu Asp Asn Gly Leu Leu Thr Ser Arg Ile Asn Leu His Cys
245 250 255
Lys Ala Ile Ile Ala Asp Tyr Ala Ser Lys Lys Gly Asp Val Lys Pro
260 265 270
Asn Ile Ile His Arg Met Leu Asp Ala Pro Glu Leu Ser Met Lys Asp
275 280 285
Lys Thr Ala Trp Arg Leu Gln Leu Glu Ala Arg Thr Leu Ile Gly Ala
290 295 300
Gly Thr Glu Thr Thr Gly His Thr Leu Ala Val Ile Ala Phe His Leu
305 310 315 320
Leu Ala Asn Pro Glu Lys Ala Lys Arg Leu Lys Glu Glu Ile Leu Ala
325 330 335
Thr Lys Glu Gly Arg Glu Lys Pro Leu Thr Tyr Gln Glu Leu Gln Met
340 345 350
Leu Pro Tyr Leu Ser Ser Val Val Leu Glu Gly His Arg Ile Ser Ser
355 360 365
Val Val Ser Gly Arg Leu Pro Arg Val Asn Thr Lys Glu Pro Leu Arg
370 375 380
Tyr Gly Asp Tyr Ser Ile Pro Ile Gly Thr Pro Val Ser Thr Thr Gln
385 390 395 400
Arg Leu Thr His Tyr Asn Ala Thr Ile Phe Pro Ser Pro Asn Thr Phe
405 410 415
Leu Pro Glu Arg Trp Leu Gln Pro Ser Glu Arg Lys Arg Leu Glu Lys
420 425 430
Tyr Ile Gln Pro Phe Gly Arg Gly Ser Arg Ser Cys Ile Gly Met His
435 440 445
Leu Ala Asn Ala Glu Ile Tyr Lys Thr Leu Ala Glu Met Phe Ala Arg
450 455 460
Phe Asp Met Lys Leu Tyr Asp Thr Glu Phe Glu Asp Ile Met Gln Val
465 470 475 480
His Asp Phe Phe Thr Ser Phe Pro Ser Ser Glu Arg Gly Leu Arg Ile
485 490 495
Leu Val Glu Ala
500
<210> 33
<211> 1802
<212> DNA
<213> Artificial Sequence
<220>
<223> CEp450-3 核苷酸序列(含内含子)
<400> 33
atgataaatc ttgcaagtcc cctcttcgca acaacagcag ttctagtctg gctcagcagt 60
ctcataatct atcgcctata tctctctcca ctatctcgat ttcccggccc aaaactcgct 120
gctctaacag gatggtacga gacatacttc gacctcttta aacggggtcg ctactggatc 180
gagattgaac gcatgcacga agtctatggt aagtttgtat tttcttcaat aaaaagcgga 240
tatattttga caccagccag gccctatcat ccgcatcaat cccaatgagc tacatgttaa 300
tgacccagaa tggaatgagc cctacaagat cagcggccgc gttgacaagt atgactggta 360
ctacaccttt gttggtagtt ccggatcctc atctgcattc ggaaccatag accacgacgt 420
tcatcgtggc cgccggaaag ctcaacaggg ctatttcacc accgacgcca tcacgcgctt 480
tgaaccacat ttagaaaccc tgacagcaaa gttctgcgca agactagacg gcttcaaggg 540
gacgggaaag catgttaatc tctccgatgc gttccgatca atcgcggtgg atgtggccgc 600
gatgtttaca ttgaatcaat cgtatggttt catcgatgac ccggatttca aggccgaggt 660
ccatcaaggg atccgggcat ttccggatat tggagtgctg aatcgccatt ttacgggttt 720
gttcgtggtt ttggagtcaa tccatagatg ggtgttgagt gttatcaacc cgtcagaaga 780
agataatggg ttactcacaa gtgtacgtat ctttccacta atactgcttt ccccgagatc 840
ctaatgcgtg atagagaata aacctgcatt gtaaagctat tattgccgac tacgccagta 900
agaaaggcga cgtcaagccc aatatcattc acagaatgct agacgcacca gaactatcga 960
tgaaagataa gacagcgtgg cgccttcaat tggaggcgcg cacccttata ggagctggaa 1020
ctgaaacgac aggacacaca ttagccgtca tagcattcca tctgctagca aatccggaga 1080
aggcaaagag gttgaaggag gagatcttag ctacgaaaga agggcgggaa aagcctttaa 1140
cttatcagga gttacaaatg cttccgtatt tagtgagtgt attgttatgg tctgcagagc 1200
atggctaatg aaagcagtct tctgtggtcc ttgaaggtca tcggtaggga gttgattttt 1260
acttttcaga agatgaggct aataacctgt agcatttcta gtgttgtatc aggtcgtctg 1320
ccacgggtca atacaaaaga gccgctcaga tatggtgact atagtatccc tattggcgca 1380
agttttcctc tcctttcgct ctctttctat aactgacgga ttagacagac acccgtcagc 1440
accacccaac ggttaacaca ctacaatgcc accatattcc cctccccaaa cacattcctc 1500
cccgaacgtt ggcttcagcc ctcggaacga aagcgcctgg agaaatacat ccagccgttc 1560
gggcgtggct caagatcttg tataggcatg cagtaagtct cgtcccctat tcgagtgtga 1620
ctaaaatgac taatgagaga agtcttgcaa atgcagagat ttacaaaaca ttggcggaga 1680
tgtttgcaag gtttgacatg aagttatatg atacggagtt cgaggatatt atgcaagtgc 1740
atgacttttt tacttcgttt ccatcgagcg agaggggttt aagaatactt gtggaagcat 1800
aa 1802
<210> 34
<211> 331
<212> PRT
<213> Artificial Sequence
<220>
<223> CEOXY2氨基酸序列
<400> 34
Met Ala Val Gln Thr Ile Gln Thr Leu Asp Tyr Arg Asp Phe Gln Asp
1 5 10 15
Gly Ser Pro Glu Gln Ser Lys Lys Phe Cys Gln Ala Leu Cys Asp Thr
20 25 30
Leu Ser Thr Trp Gly Phe Ala Lys Ile Arg Asn Ser Thr Ile Pro Asp
35 40 45
Ala Val Ile Asp Glu Leu Phe Gln Tyr Asn Lys Arg Phe Phe Ala Leu
50 55 60
Pro Glu Asn Ile Lys His Lys Ala Ala His Pro Ala Ala Pro Asn Pro
65 70 75 80
His Arg Gly Trp Ser Ala Val Gly Gln Glu Gln Leu Ser Arg Ile Ala
85 90 95
Gly Phe Glu Lys Asp Glu Glu Arg Asp Gly Phe Val Pro Glu Phe Arg
100 105 110
Glu Ser Phe Asp Gln Gly Ala Ala Asp Asp Glu Leu Phe Pro Asn Arg
115 120 125
Trp Val Asp Glu Ser Asp Leu Pro Gly Phe Arg Lys Phe Met Glu Asn
130 135 140
Tyr Tyr Asp Gln Cys His Asn Phe His Asn His Leu Leu Arg Ala Ile
145 150 155 160
Ser Ala Gly Leu Asn Leu Pro Glu Asp Leu Leu Leu Ser Arg His Gln
165 170 175
Thr Asp Thr Ser Glu Leu Arg Ile Leu His Tyr Pro Ser Ile Pro Cys
180 185 190
Ala Gln Leu Lys Ser Ala Met Arg Ile Gly Glu His Ser Asp Phe Gly
195 200 205
Thr Leu Thr Leu Leu Leu Gln Asp Ser Val Gly Gly Leu Gln Val Glu
210 215 220
Asp Gln Lys Arg Pro Gly Thr Phe Ile Pro Val Glu Ser Asp Ser Ile
225 230 235 240
Tyr Glu Ile Ile Ile Asn Val Gly Asp Cys Leu Gln Arg Trp Thr Asn
245 250 255
Arg Glu Leu Gln Ser Ala Asn His Arg Val His Leu Pro Glu Gly Lys
260 265 270
Asp Ala Lys Ser Gly Asp Val Leu Ala Glu Arg Tyr Ser Val Ala Tyr
275 280 285
Phe Gly Lys Pro Asp Arg Glu Val Leu Val Asp Thr Leu Pro Glu Phe
290 295 300
Cys Arg Asp Gly Lys Ser Arg Tyr Asn Asp His Met Asn Ala Leu Gln
305 310 315 320
Tyr Asn Gln Thr Lys Leu Leu Arg Thr Tyr Ala
325 330
<210> 35
<211> 1107
<212> DNA
<213> Artificial Sequence
<220>
<223> CEOXY2核苷酸序列(含内含子)
<400> 35
atggcagttc aaacaattca aacactcgac tatcgagact tccaggatgg cagcccagag 60
caaagtaaaa agttctgtca agctctctgt gacactttgt cgacttgggg ctttgctaaa 120
atccgaaact caactatccc agacgctgtc atagatgagc tcttccaata tgtcagtcta 180
ctcaatccca aactcatgag acaactgtct aactcattac cagaacaaac gcttctttgc 240
cttacctgaa aatatcaagc ataaggcggc tcatcccgca gcacccaatc cacatcgagg 300
ttggagtgct gtcggccagg agcaattatc tagaatcgcc ggctttgaaa aagatgaaga 360
gcgcgacggt ttcgttcccg agttccgggt acgtctcatg atagatagtc ggatcgtttg 420
tccgaggagt gctaactgag cgaacaggag tccttcgatc aaggggccgc cgatgatgag 480
cttttcccca atcgttgggt tgatgagagt gacttgccag ggtttcgaaa atttatggag 540
aattactatg atcagtgcca caacttccac aaccatcttc ttcgggcaat ctcggctggg 600
ttaaatcttc ctgaagatct ccttctctca agacaccaga ccgacactag cgagcttcgg 660
attcttcact atccttcgat accttgtgcg caactaaaat cggctatgag gattggcgag 720
cactcagact ttggaaccct taccctctta ctccaggact cggtcggtgg cttgcaggtc 780
gaggatcaga aaaggccagg cacatttatt cccgtggagt cagacagtat ctacgaaatt 840
atcatcaatg ttggagactg cttgcaacgc tggacaaaca gggagctcca atcagcaaac 900
caccgagtgc atctccctga aggtaaagac gccaagtctg gggatgtttt ggctgagcgc 960
tattcggtgg catattttgg caaaccggac agagaagtat tggttgacac acttccggaa 1020
ttttgtagag atggaaagag caggtacaac gatcatatga atgcgctgca gtacaaccag 1080
acaaaattgc tgcgtacata tgcgtag 1107
<210> 36
<211> 328
<212> PRT
<213> Artificial Sequence
<220>
<223> CEOXY3氨基酸序列
<400> 36
Met Asp His Thr Lys Glu Thr Glu Asn Ser Pro Leu Ser Ser Leu Ser
1 5 10 15
Leu Ser Gln Leu Glu Ala Asn Ile Pro Glu Glu Ser Lys Arg Leu Phe
20 25 30
Glu Ala Cys Val Asn Glu Gly Phe Phe Tyr Leu Asp Leu Arg Asp His
35 40 45
Lys Gln Leu Leu Ser Asp Tyr Asp Ala Leu Leu Glu Ile Met Lys Asn
50 55 60
Tyr Phe Asp Gln Ser Leu Asp Gln Lys Met Lys Asp Asp Arg Lys Ser
65 70 75 80
Asp Thr Val Gly Tyr Glu Pro Val Ala Thr Ser Ala Gly Ala Leu Asp
85 90 95
Gly Leu Pro Asp Tyr Tyr Glu Ser Phe Lys Val Ser Trp Asp Gln Leu
100 105 110
Arg Asn Gly Asp Gln Asp Ile Ser Ala Val Val Gln Glu Asn Met Asp
115 120 125
Val Phe Asp Arg Phe Thr Lys Cys Ala His Ser Leu Leu Leu Met Ile
130 135 140
Leu Thr Arg Leu Ser Asp Thr Met Gly Tyr Asp Gly Asn Arg Arg Phe
145 150 155 160
Glu Ala Ser His Lys Asp Gly Thr Val Thr Arg Thr Asn Leu Thr Phe
165 170 175
Leu Lys Tyr Pro Lys Gln Asn Thr Val Glu His Gly Val Gly His Asn
180 185 190
Arg His Thr Asp Ile Gly Thr Leu Thr Phe Leu Leu Ser Gly Gln Arg
195 200 205
Gly Leu Gln Arg Leu Thr Thr Asp Gly Trp Cys Asp Val Glu Pro Arg
210 215 220
Pro Gly Phe Ala Val Val Asn Val Gly Asp Ser Leu Arg Phe Leu Ser
225 230 235 240
Asp Cys Ala Phe Ser Ser Ile Ile His Arg Val Leu Pro Val Gly Ser
245 250 255
Arg Gln Thr Glu Asp Arg Tyr Thr Leu Ala Tyr Phe Leu Arg Pro Glu
260 265 270
Asp Glu Ala Val Phe Lys Asp Leu Asn Gly Asn Leu Ile Ser Ala Lys
275 280 285
Ser Trp His Asp Arg Lys Phe Asp His Phe Arg Glu Ser His Asp Gln
290 295 300
Gln Lys Lys Ala Ser Ile Leu Thr Gly Gly Met Glu Glu Asn Gln Lys
305 310 315 320
Phe Leu Gln Ser Lys Ile Gln Ala
325
<210> 37
<211> 1045
<212> DNA
<213> Artificial Sequence
<220>
<223> CEOXY3 核苷酸序列(含内含子)
<400> 37
atggatcaca ccaaggaaac tgaaaactcg ccactatctt ctttgtctct atcccaactc 60
gaggccaaca tcccagaaga atcaaaaagg ctttttgaag catgtgtgaa cgaaggattc 120
ttctacttgg atctgcgaga tcacaaacaa ttacttagcg actatgatgc gctgcttgaa 180
atcatgaaaa attactttga tcaatctctg gatcaaaaga tgaaggacga ccgcaaaagt 240
gatacagtcg gttacgaacc cgtcgcaacc tctgctggag cactagatgg gttgccagat 300
tactacgagt ctttcaaggt accaattatt ctgcggcctg tagaattaca tattgcatga 360
tactgacaac tttcaggttt catgggacca actgagaaat ggtgatcagg acatttccgc 420
cgttgtccag gaaaatatgg atgtgttcga tcgctttacg aagtgtgccc acagtttgct 480
tctgatgatc ttgactcgtc tctcggacac catgggttac gatggtaaca ggcgctttga 540
ggcttctcac aaagatggca ctgttaccag aacaaacctc acttttctca aatacccaaa 600
gcagaataca gtagagcatg gcgtgggaca taaccggcat acggacattg gcacgttgac 660
ctttctcctc agtggtcagc gcggtctgca acgacttaca acagacggtt ggtgtgatgt 720
agagccccgt ccaggatttg cagttgtcaa cgttggtgat tctttgaggt tcctgtcgga 780
ctgtgcgttc tcatctatta tacacagagt actgccagtg ggatcccgcc agactgaaga 840
caggtacaca ttggcatatt tcctgcgccc tgaagatgaa gccgtcttta aggacctgaa 900
tggaaatctg atcagtgcca aatcatggca cgaccgcaag ttcgaccatt tcagagagtc 960
tcatgaccaa cagaagaaag cgtccatctt aactggtggc atggaggaaa atcagaagtt 1020
cttgcagagc aagatccagg cttag 1045
<210> 38
<211> 4140
<212> DNA
<213> Artificial Sequence
<220>
<223> Cas9的DNA序列
<400> 38
atggacaaga agtacagcat tggcctggac attggcacga actcggtcgg ctgggccgtc 60
atcacggacg agtacaaggt cccctccaag aagtttaagg tcctgggcaa caccgaccgc 120
cactccatca agaagaacct cattggcgcc ctgctcttcg actccggcga gaccgccgag 180
gccacccgcc tcaagcgcac cgcccgccgc cgatacacgc gccgcaagaa ccgcatctgc 240
tacctgcagg agattttctc caacgagatg gccaaggtcg acgactcctt ctttcaccgc 300
ctggaggagt cgttcctcgt cgaggaagac aagaagcacg agcgccaccc catctttggc 360
aacattgtcg acgaggtcgc ctaccacgag aagtacccca cgatctacca cctgcgcaag 420
aagctcgtcg actccaccga caaggccgac ctccgcctga tctacctcgc cctggcccac 480
atgattaagt tccgcggcca ctttctgatc gagggcgacc tcaaccccga caacagcgac 540
gtcgacaagc tgttcatcca gctcgtccag acctacaacc agctctttga ggagaacccc 600
attaacgcct ccggcgtcga cgccaaggcc atcctctcgg cccgcctctc caagagccgc 660
cgactcgaga acctgatcgc ccagctgccc ggcgagaaga agaacggcct gttcggcaac 720
ctcatcgccc tctccctggg cctcaccccc aacttcaagt cgaactttga cctcgccgag 780
gacgccaagc tgcagctctc caaggacacc tacgacgacg acctggacaa cctcctggcc 840
cagatcggcg accagtacgc cgacctgttc ctcgccgcca agaacctgtc cgacgccatc 900
ctcctgtcgg acattctccg cgtcaacacc gagattacga aggcccctct ctccgcctcg 960
atgatcaagc gctacgacga gcaccaccag gacctgaccc tgctcaaggc cctggtccgc 1020
cagcagctcc ccgagaagta caaggagatc ttctttgacc agagcaagaa cggctacgcc 1080
ggctacatcg acggcggcgc tagccaagag gagttctaca agtttatcaa gcccattctg 1140
gagaagatgg acggcacgga ggagctcctg gtcaagctca accgcgagga cctcctgcgc 1200
aagcagcgca ccttcgacaa cggcagcatc ccccaccaga ttcacctcgg cgagctgcac 1260
gccatcctcc gccgacaaga ggacttctac ccctttctca aggacaaccg cgagaagatc 1320
gagaagattc tgacgttccg catcccctac tacgtcggcc ccctggcccg cggcaacagc 1380
cgctttgcct ggatgacccg caagtccgag gagaccatca cgccctggaa cttcgaggaa 1440
gtcgtcgaca agggcgcctc ggcccagtcc ttcatcgagc gcatgaccaa ctttgacaag 1500
aacctgccca acgagaaggt cctccccaag cactcgctcc tgtacgagta cttcaccgtc 1560
tacaacgagc tcacgaaggt caagtacgtc accgagggca tgcgcaagcc cgccttcctg 1620
tcgggcgagc agaagaaggc catcgtcgac ctcctgttta agaccaaccg caaggtcacg 1680
gtcaagcagc tcaaggaaga ctacttcaag aagattgagt gctttgacag cgtcgagatc 1740
tccggcgtcg aggaccgctt taacgcctcc ctgggcacct accacgacct cctgaagatc 1800
attaaggaca aggacttcct ggacaacgag gagaacgagg acatcctcga ggacattgtc 1860
ctgaccctca cgctgtttga ggaccgcgag atgatcgagg agcgcctgaa gacgtacgcc 1920
cacctcttcg acgacaaggt catgaagcag ctcaagcgcc gccgatacac cggctggggc 1980
cgcctgagcc gcaagctcat caacggcatt cgcgacaagc agtcgggcaa gacgatcctc 2040
gacttcctga agagcgacgg cttcgccaac cgcaacttta tgcagctgat tcacgacgac 2100
tccctcacct tcaaggaaga catccagaag gcccaggtct ccggccaggg cgactccctg 2160
cacgagcaca tcgccaacct cgccggcagc cccgccatca agaagggcat tctgcagacc 2220
gtcaaggtcg tcgacgagct cgtcaaggtc atgggccgcc acaagcccga gaacatcgtc 2280
attgagatgg cccgcgagaa ccagaccacg cagaagggcc agaagaacag ccgcgagcgc 2340
atgaagcgca tcgaggaagg catcaaggag ctgggctccc agatcctcaa ggagcacccc 2400
gtcgagaaca cccagctgca gaacgagaag ctctacctgt actacctcca gaacggccgc 2460
gacatgtacg tcgaccagga gctggacatt aaccgcctct cggactacga cgtcgaccac 2520
atcgtccccc agagcttcct gaaggacgac tccatcgaca acaaggtcct cacccgcagc 2580
gacaagaacc gcggcaagag cgacaacgtc ccctccgagg aagtcgtcaa gaagatgaag 2640
aactactggc gccagctcct gaacgccaag ctgatcacgc agcgcaagtt tgacaacctc 2700
accaaggccg agcgaggcgg cctctcggag ctggacaagg ccggcttcat caagcgccag 2760
ctggtcgaga cccgccagat cacgaagcac gtcgcccaga ttctcgactc gcgcatgaac 2820
acgaagtacg acgagaacga caagctgatc cgcgaggtca aggtcattac cctgaagtcg 2880
aagctcgtca gcgacttccg caaggacttc cagttttaca aggtccgcga gatcaacaac 2940
taccaccacg cccacgacgc ctacctcaac gccgtcgtcg gcaccgccct gatcaagaag 3000
taccccaagc tcgagtccga gttcgtctac ggcgactaca aggtctacga cgtccgcaag 3060
atgatcgcca agtccgagca ggagattggc aaggccaccg ccaagtactt cttttactcg 3120
aacatcatga acttctttaa gaccgagatc accctcgcca acggcgagat ccgcaagcgc 3180
cccctcattg agaccaacgg cgagaccggc gagatcgtct gggacaaggg ccgcgacttc 3240
gccaccgtcc gcaaggtcct cagcatgccc caggtcaaca tcgtcaagaa gaccgaggtc 3300
cagacgggcg gcttctcgaa ggagagcatt ctgcccaagc gcaactccga caagctcatc 3360
gcccgcaaga aggactggga ccccaagaag tacggtggct tcgactcccc caccgtcgcc 3420
tactcggtcc tggtcgtcgc caaggtcgag aagggcaagt cgaagaagct caagagcgtc 3480
aaggagctcc tgggcatcac cattatggag cgcagctcct tcgagaagaa ccccatcgac 3540
tttctcgagg ccaagggcta caaggaagtc aagaaggacc tgatcattaa gctccccaag 3600
tactccctct tcgagctgga gaacggccgc aagcgcatgc tcgcctccgc cggcgagctc 3660
cagaagggca acgagctcgc cctgcccagc aagtacgtca acttcctcta cctggccagc 3720
cactacgaga agctcaaggg ctcccccgag gacaacgagc agaagcagct gtttgtcgag 3780
cagcacaagc actacctcga cgagatcatt gagcagattt ccgagttctc gaagcgcgtc 3840
atcctggccg acgccaacct ggacaaggtc ctcagcgcct acaacaagca ccgcgacaag 3900
cccatccgcg agcaggccga gaacatcatt cacctcttca ccctgaccaa cctcggcgcc 3960
cccgccgcct tcaagtactt tgacaccacg atcgaccgca agcgctacac ctcgacgaag 4020
gaagtcctgg acgccaccct catccaccag agcattaccg gcctctacga gacgcgcatc 4080
gacctcagcc agctcggcgg cgactcccgc gccgacccca agaagaagcg caaggtctaa 4140
Claims (10)
1.一种基因工程菌,其特征在于,所述基因工程菌在出发菌丝状真菌Coleophomaempetri中失活编码α-酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因,其中所述α-酮戊二酸依赖性氧化酶为CEOXY1或CEOXY4,所述P450单加氧酶为CEP450-1、CEP450-2或CEP450-3。
2.如权利要求1所述的基因工程菌,其特征在于,所述出发菌为Coleophoma empetriF-11899,和/或,所述CEOXY1的氨基酸序列如SEQ ID NO:24所示,和/或,所述CEOXY4的氨基酸序列如SEQ ID NO:26所示,和/或,所述CEP450-1的氨基酸序列如SEQ ID NO:28所示,和/或,所述CEP450-2的氨基酸序列如SEQ ID NO:30所示,和/或,所述CEP450-3的氨基酸序列如SEQ ID NO:32所示;
优选地,编码所述CEOXY1的核苷酸序列如SEQ ID NO:25所示,和/或,编码所述CEOXY4的核苷酸序列如SEQ ID NO:27所示,和/或,编码所述CEP450-1的核苷酸序列如SEQ ID NO:29所示,和/或,编码所述CEP450-2的核苷酸序列如SEQ ID NO:31所示,和/或,编码所述CEP450-3的核苷酸序列如SEQ ID NO:33所示。
3.一种如权利要求1或2所述的基因工程菌的构建方法,其特征在于,所述构建方法为在出发菌中使如权利要求1或2所述的基因工程菌中所定义的编码α-酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因失活;
优选地,所述失活为在所述出发菌中导入cas9***和靶向如权利要求1或2中所定义的编码α-酮戊二酸依赖性氧化酶和/或P450单加氧酶的基因的sgRNA表达盒。
4.如权利要求3所述的构建方法,其特征在于,所述cas9***包含编码cas9酶的基因,所述sgRNA表达盒包含能够特异性识别目的基因的N20片段;优选地,
所述编码cas9酶的基因的核苷酸序列如SEQ ID NO:38所示;和/或,
所述N20片段的核苷酸序列如SEQ ID NO:1、SEQ ID NO:2、SEQ ID NO:3、SEQ ID NO:4和/或SEQ ID NO:5所示;和/或,
所述导入的方法为农杆菌介导法。
5.一种FR901379衍生物,其特征在于,所述FR901379衍生物的结构如式I所示:
其中,R1为H;R2、R4和R5独立地为H或OH;R3为C1-6烷基或H,优选为甲基;R6为H或;X+为一价阳离子;
或,R3为H;R1、R2、R4和R5独立地为H或OH;R6为H或X+为一价阳离子;
或,R1、R2和R4为OH;R3为C1-6烷基;R5和R6为H;
所述X+优选为Na+、K+或NH4 +,例如为Na+;
R3中,所述C1-6烷基较佳地为甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基,更佳地为甲基;
带“*”的碳原子独立地为手性碳原子或非手性碳原子,当为手性碳原子时,独立地为R构型和/或S构型。
6.如权利要求5所述FR901379衍生物,其特征在于,所述FR901379衍生物的结构如式I-1所示:
其中,R1为H;R2为OH;R3为甲基;R4为H;R5为H;R6为OSO3Na;和/或,
R1为OH;R2为OH;R3为H;R4为OH;R5为OH;R6为OSO3Na;和/或,
R1为OH;R2为OH;R3为H;R4为OH;R5为H;R6为OSO3Na;和/或,
R1为OH;R2为H;R3为H;R4为OH;R5为H;R6为OSO3Na;和/或,
R1为H;R2为H;R3为甲基;R4为OH;R5为H;R6为OSO3Na;和/或,
R1为OH;R2为OH;R3为甲基;R4为OH;R5为H;R6为H。
7.如权利要求6所述FR901379衍生物,其特征在于,所述FR901379衍生物为以下任一化合物:
8.一种制备FR901379衍生物的方法,其特征在于,所述方法包括在发酵培养基中培养如权利要求1或2所述的基因工程菌,使其表达产生FR901379衍生物;所述FR901379衍生物为如权利要求5~7任一项所定义,或为FR901381或FR901382。
9.如权利要求8所述的方法,其特征在于,所述发酵培养基的pH值为6.0~7.0,和/或,所述发酵培养基包含80~120g/L甘露醇,4~6g/L棉籽饼粉,8~12g/L黄豆饼粉,3~5g/LK2HPO4和0.8~1.2g/L CaCO3;和/或,
所述培养的温度为23~27℃,和/或,所述培养的转速为200~240rpm,和/或,所述培养的时间为8~12天;
所述发酵培养基的pH值优选6.5;
所述甘露醇优选100g/L,所述棉籽饼粉优选5g/L,所述黄豆饼粉优选10g/L,所述K2HPO4优选4g/L,所述CaCO3优选1g/L;
所述温度优选25℃;所述转速优选220rpm;所述时间优选10天。
10.如权利要求1或2所述的基因工程菌在生产FR901379衍生物中的应用;优选地,所述FR901379衍生物如权利要求5~7任一项所定义,或所述FR901379衍生物为FR901381或FR901382。
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