CN116875645A - 一种生物酶法合成胞苷二磷酸的方法 - Google Patents
一种生物酶法合成胞苷二磷酸的方法 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 38
- ZWIADYZPOWUWEW-XVFCMESISA-N CDP Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1 ZWIADYZPOWUWEW-XVFCMESISA-N 0.000 title claims abstract description 35
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 21
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
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- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 claims abstract description 15
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims abstract description 15
- 108020000161 polyphosphate kinase Proteins 0.000 claims abstract description 13
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 8
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 8
- PSDHRHUVDFEMBQ-UHFFFAOYSA-L dipotassium;acetyl phosphate Chemical compound [K+].[K+].CC(=O)OP([O-])([O-])=O PSDHRHUVDFEMBQ-UHFFFAOYSA-L 0.000 claims abstract description 7
- -1 acetyl potassium phosphate Chemical compound 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 3
- 108010093096 Immobilized Enzymes Proteins 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 101001138544 Homo sapiens UMP-CMP kinase Proteins 0.000 claims description 2
- 102100020797 UMP-CMP kinase Human genes 0.000 claims description 2
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- 230000008569 process Effects 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 3
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 abstract 1
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 abstract 1
- 238000006911 enzymatic reaction Methods 0.000 abstract 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000012258 culturing Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PCDQPRRSZKQHHS-CCXZUQQUSA-N Cytarabine Triphosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 PCDQPRRSZKQHHS-CCXZUQQUSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 4
- IERHLVCPSMICTF-XVFCMESISA-N cytidine 5'-monophosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O1 IERHLVCPSMICTF-XVFCMESISA-N 0.000 description 4
- IERHLVCPSMICTF-UHFFFAOYSA-N cytidine monophosphate Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(COP(O)(O)=O)O1 IERHLVCPSMICTF-UHFFFAOYSA-N 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 108030004122 Cytidine kinases Proteins 0.000 description 3
- 102000007410 Uridine kinase Human genes 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229930183912 Cytidylic acid Natural products 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000012880 LB liquid culture medium Substances 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- BPHPUYQFMNQIOC-NXRLNHOXSA-N isopropyl beta-D-thiogalactopyranoside Chemical compound CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O BPHPUYQFMNQIOC-NXRLNHOXSA-N 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 2
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- C12P19/00—Preparation of compounds containing saccharide radicals
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- C12N9/10—Transferases (2.)
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Abstract
本发明提供一种生物酶法合成胞苷二磷酸的方法,属于生物医药技术领域。以胞苷酸和乙酰磷酸钾盐为原料,在胞苷酸激酶和多聚磷酸激酶的催化作用下发生反应生成胞苷二磷酸。与其它工艺相比,该方法采用酶促法合成胞苷二磷酸,利用乙酰磷酸钾盐作为腺苷三磷酸合成的原料,反应步骤简单,工艺周期短,具有成本较低,污染较小的特点,适宜产业化。
Description
技术领域
本发明涉及一种生物酶法合成胞苷二磷酸的方法,属于生物医药技术领域。
背景技术
胞苷二磷酸,英文名为cytidine diphosphate,简称CDP,分子式为C9H15N3O11P2,分子量为403.18,CAS登记号为63-38-7,是合成脑磷脂过程中乙醇胺的载体。工业上主要用于合成胞苷三磷酸和聚肌胞等药物。
目前胞苷二磷酸的生产方式主要是利用啤酒酵母生产胞苷二磷酸,通过先将一磷酸胞苷(CMP)合成三磷酸胞苷(CTP),再将CTP降解生成CDP的二步法来生产(王赞苗,利用啤酒酵母生产二磷酸胞苷的工艺研究[J].化学与生物工程,2005(07):52-54.)。利用啤酒酵母生产胞苷二磷酸发酵液内含有含有大量杂蛋白及其它无机物,分离难度高,工序较多,操作复杂,得率较低。
发明内容
为了克服上述技术缺陷,本发明提供了一种生物酶法合成胞苷二磷酸的方法。以胞苷酸,乙酰磷酸钾盐为原料,在胞苷酸激酶和多聚磷酸盐激酶的催化下反应得到胞苷二磷酸。该工艺所需原料来源广泛,价格便宜,反应步骤简单,产量高,反应过程温和,污染较小。
本发明所述一种生物酶法合成胞苷二磷酸的方法,包括如下步骤:以胞苷酸、乙酰磷酸钾盐和ATP为原料,采用胞苷酸激酶和多聚磷酸盐激酶共同作用下进行生物转化,得到胞苷二磷酸。采用反应方程式表示为:
进一步地,在上述技术方案中,所述胞苷酸激酶序列为序列表中(1)SEQ IDNO.1所示核苷酸序列。
进一步地,在上述技术方案中,所述多聚磷酸激酶序列为序列表中SEQ ID NO.2所示的核苷酸序列。
进一步地,在上述技术方案中,反应在25-35℃和pH=6.0-8.0条件下进行。
进一步地,在上述技术方案中,反应加入MgCl2或MgSO4。
进一步地,在上述技术方案中,所述胞苷酸浓度为200-400mM,乙酰磷酸钾盐浓度为400-1000mM,ATP浓度为15-25mM。
进一步地,在上述技术方案中,所述乙酰磷酸钾盐乙酰磷酸钾盐作为磷酸供体,为液体型试剂。
进一步地,在上述技术方案中,所述胞苷酸激酶和多聚磷酸盐激酶包括但不局限于酶液、酶冻干粉、含酶细胞以及各种固定化酶和固定化酶细胞。例如未经纯化的粗酶形式、经部分纯化或完全纯化的形式。
发明有益效果
1、生物酶法合成胞苷二磷酸的方法,与目前现有利用啤酒酵母生产胞苷二磷酸的工艺不同,本发明反应步骤简单,对环境更为友好。
2、生物酶法合成胞苷二磷酸的方法,与目前现有以多聚磷酸盐作为磷酸供体的技术不同,本发明以价格更为低廉乙酰磷酸钾盐为磷酸供体,极大降低了生产成本。
3、生物酶法合成胞苷二磷酸的方法,产品胞苷二磷酸的产物浓度达到75g/L。
说明书附图
图1为实施例3中温度对反应收率影响图;
图2为实施例4中pH对反应收率影响图;
图3为实施例5中反应液胞苷二磷酸HPLC谱图。
具体实施方式
实施例1胞苷酸激酶的发酵培养:
发酵培养基配方:葡萄糖30g/L,七水硫酸镁0.3g/L,磷酸二氢钾3g/L,磷酸氢二钠4.8g/L,氯化铵1g/L,酵母膏20g/L,蛋白胨15g/L。
将胞苷酸激酶菌株单菌落接种到LB液体培养基,在35℃下震荡培养10-12h,以5%接种量将震荡后的培养基转接到新鲜培养基中,在35℃下震荡培养至OD600=0.6时,接种到发酵罐。发酵培养至OD600=16时加入IPTG诱导培养8h,然后离心得胞苷酸激酶菌体细胞252g。
实施例2多聚磷酸激酶的发酵培养:
发酵培养基配方:葡萄糖30g/L,七水硫酸镁0.3g/L,磷酸二氢钾3g/L,磷酸氢二钠4.8g/L,氯化铵1g/L,酵母膏20g/L,蛋白胨15g/L。
将多聚磷酸激酶菌株单菌落接种到LB液体培养基,在35℃下震荡培养10-12h,以5%接种量将震荡后的培养基转接到新鲜培养基中,在35℃下震荡培养至OD600=0.6时,接种到发酵罐。发酵培养至OD600=16时加入IPTG诱导培养8h,然后离心得多聚磷酸激酶菌体细胞265g。
实施例3温度优化反应
反应体系及反应条件:在250mL烧杯中加入50mM胞苷酸,100mM乙酰磷酸钾盐溶液,10mMATP,50mM MgCl2,加适量纯化水,用NaOH调PH至7.0-7.2,之后分别加入2g胞苷酸激酶、2g多聚磷酸盐激酶,用纯化水定容至100mL,分别在20、30、40、50、60℃条件下反应3-9h,最终测定在35℃反应温度下,反应产品浓度最佳(图1),反应过程中取样进行高效液相色谱((HPLC)检测,监控反应进程最终胞苷二磷酸的产品浓度达到15g/L。
实施例4pH优化反应
反应体系及反应条件:在250mL烧杯中加入50mM胞苷酸,100mM乙酰磷酸钾盐溶液,10mMATP,50mM MgCl2,加适量纯化水,之后分别加入2g胞苷酸激酶、2g多聚磷酸盐激酶,用纯化水定容至100mL,分别用碱调节pH为5.0、6.0、7.0、8.0、9.0,最终测定在pH为7.0-7.2,产物转化率最佳,在35℃水浴锅中反应8h(图2),反应过程中取样进行高效液相色谱(HPLC)检测,监控反应进程。最终胞苷二磷酸的产品浓度达到25g/L。
实施例5酶法合成胞苷二磷酸的方法
反应体系及反应条件:在250mL烧杯中加入300mM胞苷酸,500mM乙酰磷酸钾盐溶液,25mMATP,50mM MgCl2,加适量纯化水,用1.5M NaOH调pH至7.0-7.2,之后分别加入2g胞苷酸激酶、2g多聚磷酸盐激酶,用纯化水定容至100mL,在35℃水浴锅中反应8h,反应过程中取样进行高效液相色谱((HPLC)检测,监控反应进程(图3)。最终胞苷二磷酸的产品浓度达到75g/L。
以上实施例描述了本发明的基本原理、主要特征及优点。本行业技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书的描述只是用来解释本发明的原理,在不脱离本发明原理的范围下,本发明还会有各种变化和改进,这些变化和改进均落入本发明保护的范围内。
Claims (6)
1.一种生物酶法合成胞苷二磷酸的方法,其特征在于:以胞苷酸、乙酰磷酸钾盐和ATP为原料,在胞苷酸激酶和多聚磷酸激酶催化下发生反应,制得胞苷二磷酸。
2.根据权利要求1所述生物酶法合成胞苷二磷酸的方法,其特征在于:乙酰磷酸钾盐作为磷酸供体,为液体型试剂。
3.根据权利要求1所述生物酶法合成胞苷二磷酸的方法,其特征在于:反应在25-35℃和pH=6.0-8.0条件下进行。
4.根据权利要求1所述生物酶法合成胞苷二磷酸的方法,其特征在于:反应过程中加入MgCl2或MgSO4。
5.根据权利要求1所述生物酶法合成胞苷二磷酸的方法,其特征在于:所述胞苷酸浓度为50-400mM,乙酰磷酸钾盐浓度为100-1000mM,ATP浓度为15-25mM。
6.根据权利要求1所述生物酶法合成胞苷二磷酸的方法,其特征在于:所述胞苷酸激酶和多聚磷酸盐激酶包括酶液、酶冻干粉、含酶细胞以及各种固定化酶或固定化酶细胞。
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