CN111718966A - 一种丁香酚的微生物合成方法 - Google Patents
一种丁香酚的微生物合成方法 Download PDFInfo
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- CN111718966A CN111718966A CN202010524389.5A CN202010524389A CN111718966A CN 111718966 A CN111718966 A CN 111718966A CN 202010524389 A CN202010524389 A CN 202010524389A CN 111718966 A CN111718966 A CN 111718966A
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Abstract
本发明公开了一种丁香酚的微生物合成方法。本发明提供的松柏醇酰基转移酶CFAT，其氨基酸序列和其核苷酸序列分别用SEQ ID No.1和SEQ ID No.2所示，丁香酚合成酶EGS2、APS1和AIS1,其核苷酸序列分别用SEQ ID No.6、SEQ ID No.9和SEQ ID No.11所示。松柏醇酰基转移酶和丁香酚合成酶EGS2组合，或松柏醇酰基转移酶和丁香酚合成酶APS1组合，或松柏醇酰基转移酶和丁香酚合成酶AIS1组合，能高效催化松柏醇合成丁香酚，减少中间体积累，为微生物发酵丁香酚的工业化生产奠定了基础。
Description
技术领域
本发明所属生物农药技术领域，涉及一种松柏醇酰基转移酶和三种丁香酚合成酶在微生物中转化松柏醇合成丁香酚中的应用。
背景技术
丁香酚是一种高效的植物源生物农药，主要用于防治番茄灰霉病、葡萄霜霉病和马铃薯晚疫病等重要的农业病害。目前国内采用从丁香等植物中提取制备丁香酚，存在含量低、生长缓慢等原料来源问题。
据文献报道，松柏醇酰基转移酶(CFAT)可催化松柏醇发生酰基化反应生成乙酸松柏酯，丁香酚合成酶(EGS)催化乙酸松柏酯发生还原反应生成丁香酚，其途径如图1所示。
松柏醇酰基转移酶(CFAT)属于BAHD酰基转移酶家族，已经从矮牵牛、樱桃李、苹果等植物中鉴定了基因并进行酶学表征[1-4]。丁香酚合成酶是NADPH依赖性还原酶，将乙酸松柏酯侧链上的酯键还原成烯丙基。目前已经有罗勒、啤酒花、牵牛、月季、草莓、手参等多种植物来源的丁香酚合成酶被鉴定[5-9]。在大肠杆菌异源合成丁香酚产量低，在20mg/L以下。如LtCAAT1/LtAPS1的组合，合成了约27mg/L丁香酚[10]，是目前文献报道最高产量。
[1]Dexter R,Qualley A,Kish C M,et al.Characterization of a petuniaacetyltransferase involved in the biosynthesis of the floral volatileisoeugenol[J].Plant J.,2007,49(2):265-275.
[2]Koeduka T,Orlova I,Baiga T J,et al.The lack of floral synthesisand emission of isoeugenol in petunia axillaris subsp.Parodii is due to amutation in the isoeugenol synthase gene[J].Plant J., 2009,58(6):961-969.
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发明内容
为了解决现有技术中存在的问题，本发明提供一种丁香酚的微生物合成方法，解决现有技术中制备丁香酚含量低的问题。
本发明的技术方案概述如下：
一种丁香酚的微生物合成方法，组合表达松柏醇酰基转移酶CFAT和丁香酚合成酶EGS2，以松柏醇为底物直接合成丁香酚。所述松柏醇酰基转移酶CFAT的氨基酸序列和基因序列分别如SEQ ID No.1和SEQ ID No.2所示，丁香酚合成酶EGS2的氨基酸序列和基因序列分别如SEQ ID No.5和SEQ ID No.6所示。
一种丁香酚的微生物合成方法，组合表达松柏醇酰基转移酶CFAT和丁香酚合成酶APS1，以松柏醇为底物直接合成丁香酚。所述松柏醇酰基转移酶CFAT的氨基酸序列和基因序列分别如SEQ ID No.1和SEQ ID No.2所示，丁香酚合成酶APS1的基因序列如SEQ IDNo.9所示。
一种丁香酚的微生物合成方法，组合表达松柏醇酰基转移酶CFAT和丁香酚合成酶AIS1，以松柏醇为底物直接合成丁香酚。所述松柏醇酰基转移酶CFAT的氨基酸序列和基因序列分别如SEQ ID No.1和SEQ ID No.2所示，丁香酚合成酶AIS1的氨基酸序列和基因序列分别如SEQ ID No.10和SEQ ID No.11所示。
松柏醇酰基转移酶CFAT和丁香酚合成酶EGS2或APS1或AIS1组合，以松柏醇为底物，在丁香酚合成中的应用。
本发明的优点：
本发明通过微生物法转化松柏醇生成丁香酚，并筛选到一种松柏醇酰基转移酶和三种丁香酚合成酶的组合表达，建立生物合成方法，以松柏醇为底物直接合成了丁香酚。本发明通过大肠杆菌表达，筛选出最优酶及其组合，丁香酚产量达到200mg/L以上，有利于工业化生产丁香酚。
附图说明
图1为微生物法转化松柏醇生成丁香酚途径；
图2为菌株BEG1发酵样品气相色谱图；
图3为菌株BEG1发酵样品质谱图；
图4为丁香酚标准品质谱图。
具体实施方式
本发明所用大肠杆菌菌株E.coli BL21(DE3)和E.coli DH5α购买自北京全式金生物技术有限公司。
LB培养基组成为：10g/L NaCl、10g/L蛋白胨和5g/L酵母粉，余量为水，0.1Mpa压力121℃下灭菌20min。
M9Y培养基组成为：6.8g/L Na2HPO4、3.0g/LKH2PO4、1.0g/L NaCl、0.5g/L NH4Cl、1.0 g/L酵母粉，余量为水，培养基在0.1Mpa压力121℃下灭菌20min。灭菌完后加入终浓度为2mM MgSO4、0.1mM CaCl2和10g/L葡萄糖。
下面结合具体实施例对本发明作进一步的说明。
实施例1(类)松柏醇酰基转移酶的获得
松柏醇酰基转移酶可催化松柏醇发生酰基化反应生成乙酸松柏酯，通过生物信息分析和序列比对等方式挖掘，筛选出三种松柏醇酰基转移酶，它们分别是CFAT(GenBank:ABG75942.1)、 CAAT1(GenBank:KF543260.1)和AT(NCBI:NP_178020.1)。下面以松柏醇酰基转移酶PhCFAT 为例，说明如何获取(类)松柏醇酰基转移酶。
结合松柏醇酰基转移酶CFAT的氨基酸序列及大肠杆菌对密码子的偏好性，去除常用酶切位点，设计全长CFAT基因，所述核酸序列如SEQ ID No.2示。设计将CFAT基因连接在质粒 pCDFDuet-1第一个T7启动子下游，全人工合成两端分别加上Nco I和BamH I酶切位点的 PT7-CFAT基因片段，得到的基因片段命名为synCFAT。
将通过化学全合成得到的synCFAT片段，通过PCR方法扩增。用高保真DNA聚合酶，建立PCR体系。以synCFAT-F(SEQ ID No.3)和synCFAT-R(SEQ ID No.4)为引物，synCFAT 片段为模板大量扩增制备。
PCR过程是，95℃预变性5min；95℃变性15s，55℃退火15s，72℃延伸45s，循环数为30个。扩增synCFAT片段，纯化扩增产物后，备用。
采取类似方法，获得了AT和CAAT1的基因序列。
实施例2丁香酚合成酶的获得
丁香酚合成酶催化乙酸松柏酯发生还原反应生成丁香酚。通过生物信息分析和序列比对等方式挖掘，筛选出四种丁香酚合成酶。它们分别是EGS1(GenBank:ABR24113.1)、EGS2 (GenBank:AKB11750.1)、APS1(GenBank:KF543262.1)和AIS1(GenBank:ACL13526.1)。下面以丁香酚合成酶EGS2为例，说明如何获取丁香酚合成酶。
结合丁香酚合成酶EGS2的氨基酸序列及大肠杆菌对密码子的偏好性，去除常用酶切位点，设计全长EGS2基因，所述核酸序列如SEQ ID No.6示。设计将EGS2基因连接在质粒pCDFDuet-1第二个T7启动子下游，全人工合成两端分别加上Nde I和Kpn I酶切位点的PT7-EGS2基因片段，得到的基因片段命名为synEGS2。
将通过化学全合成得到的synEGS2片段，通过PCR方法扩增。用高保真DNA聚合酶，建立PCR体系。以synEGS2-F(SEQ ID No.7)和synEGS2-R(SEQ ID No.8)为引物，synEGS2 片段为模板大量扩增制备。
PCR过程是，95℃预变性5min；95℃变性15s，52℃退火15s，72℃延伸30s，循环数为30个。扩增synEGS2片段，纯化扩增产物后，备用。
采取类似方法，获得了EGS1、APS1和AIS1的基因序列。
实施例3重组表达载体的构建
将优化后的两类基因进行组合，连接至质粒pCDFDuet-1上，其中松柏醇酰基转移酶插入至酶切位点Nco I和BamH I之间，丁香酚合成酶插入至酶切位点Nde I和Kpn I之间。下面以重组表达载体pCPG1为例，说明如何构建重组表达载体。
将synPhCFAT片段使用FastDigest内切酶Nco I和BamH I进行酶切，反应体系为：5μL 10*FD buffer、2μL Nco I内切酶、2μL BamH I内切酶、41μL synCFAT片段。反应条件为：37℃， 2h。并用试剂盒纯化回收得到用Nco I和BamH I双酶切的synCFAT片段。将纯化回收后得到的synCFAT片段与用相同酶酶切得到的线性化载体骨架pCDFDuet-1(包括复制子和抗性片段部分)进行连接反应得到pCP质粒。其连接反应体系为：1μL 10*T4 DNA LigaseBuffer、1μL T4 DNA Ligase、6μL用纯化回收后得到的synCFAT片段和2μL相同酶酶切得到的线性化载体骨架。连接反应条件为：30℃，0.5h。同理，使用FastDigest内切酶Nde I和KpnI酶切synEGS2 片段和pCP质粒，各自回收纯化后再通过连接反应得到重组表达载体pCEG1。
各重组表达载体的组合如下：
pCEG1：pCDFDuet-1，PT7-CFAT-PT7-EGS2；
pCEG2：pCDFDuet-1，PT7-CFAT-PT7-APS1；
pCEG3：pCDFDuet-1，PT7-CFAT-PT7-EGS1；
pCEG4：pCDFDuet-1，PT7-CFAT-PT7-AIS1；
pCEG5：pCDFDuet-1，PT7-AT-PT7-EGS1；
pCEG6：pCDFDuet-1，PT7-AT-PT7-EGS2；
pCEG7：pCDFDuet-1，PT7-AT-PT7-APS1；
pCEG8：pCDFDuet-1，PT7-AT-PT7-AIS1；
pCEG9：pCDFDuet-1，PT7-CAAT1-PT7-EGS1；
pCEG10：pCDFDuet-1，PT7-CAAT1-PT7-EGS2；
pCEG11：pCDFDuet-1，PT7-CAAT1-PT7-APS1；
pCEG12：pCDFDuet-1，PT7-CAAT1-PT7-AIS1。
实施例4重组大肠杆菌的构建及生物转化合成丁香酚
1.重组大肠杆菌的构建
将所构建的重组表达载体电击转化进入宿主细胞E.coli BL21(DE3)中，得到重组菌株 BEG1-BEG12。
2.重组菌BEG1-BEG12生物转化合成丁香酚
将重组菌BEG1-BEG12接种在LB培养基中，37℃，220rpm，震荡培养12h，然后按1％的接种量添加到新鲜LB培养基中，培养至OD600约等于1时加入0.1mM IPTG，继续培养5-6h后等比例转接到M9Y发酵培养基中，添加400mg/L松柏醇，30℃，220rpm发酵12h，转化合成丁香酚。
发酵结束后，取有机相50μL，稀释至10倍体积的乙酸乙酯溶剂中，震荡混匀2min，除水，用0.22μm的微孔滤膜过滤后进行气相色谱(GC)系统检测。气相色谱仪仪器型号为Agilent 7820A，气相色谱柱为HP-5(30m*0.25mm，0.25μm film thick ness)，检测器为FID火焰检测器。升温程序为初始温度60℃，保持1min，20℃/min升到240℃，保持5min，之后10℃/min 升到280℃，然后320℃后运行8min。进样口温度为280℃，检测器温度为320℃。氮气的流速为3mL/min，分流比为10。
如图2所示，气相检测出现了新峰，与丁香酚标准品具有相同的保留时间。进一步质谱分析，如图3所数据显示，新合成的产物与丁香酚标准品(图4)具有相同的离子图谱，为此新合成的产物为丁香酚。进行计算，各菌株合成丁香酚的产量如表1所示，其在12个菌株中，菌株BEG1合成最多的丁香酚，为207.32mg/L；其次是BEG2和BEG4，丁香酚产量分别为196.30mg/L和188.71mg/L；其余菌株都较低，在30mg/L以下。实验数据表明，CFAT和丁香酚合成酶EGS2组合表达较其它组合而言更具有优势，其次是松柏醇酰基转移酶CFAT分别和丁香酚合成酶APS1以及丁香酚合成酶AIS1的组合表达，但都远高于AT和CAAT1与丁香酚合成酶组合表达的效果，说明松柏醇酰基转移酶CFAT较AT和CAAT1而言，更适合用于丁香酚生物合成过程。
表1.菌株发酵结果
以上对本发明做了示例性的描述，应该说明的是，在不脱离本发明的核心的情况下，任何简单的变形、修改或者其他本领域技术人员能够不花费创造性劳动的等同替换均落入本发明的保护范围。
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ggaaacccta aagccataca tgtggacgag cgtgacattg ccacatattc catcaaggcg 660
gcagacgatg aaaggactct gaacaaaata ttatacataa ggccgcccgc caacatctac 720
tccgtcaatg aactcgtgtc gctttgggag acgaagacga acaaaacact cgaaagaata 780
tatgtttccg aagaagaagt cttgaaaaag ataaatgaat ctcctgggca actgcctttc 840
ttttacgcag tcgcgtatgc cggattcatc aagggactaa cgacaaattt cgacatagat 900
ccatcaatcg gagtcgaggc ctccatcctc tacccagatg tcgaatacac taccgtcgag 960
aagtttatgg accgctttct ataa 984
<210> 7
<211> 27
<212> DNA
<213> 人工序列
<400> 7
ggaattccat atgagcagcc agatcat 27
<210> 8
<211> 30
<212> DNA
<213> 人工序列
<400> 8
ggggtacctt acagaaaacg atccatgaat 30
<210> 9
<211> 927
<212> DNA
<213> 人工序列
<400> 9
atggcacaga agagcaagat tttgatcatt ggaggcactg gctatattgg caaattcgtt 60
gttgaagcaa gcgctaaggc tggccgtcct acctttgcat tagttagaga aagcactgtt 120
tctgaccctg ttaaaggaaa gcttattgca aacttcaaga atttgggtgt caatattctc 180
catggagatc tcaatgatca cgagagctta gtgaaggcaa ttaagaaggt ggatgtggtc 240
atttctacag taggcaactt tcagatagct gatcaagtca agattattgc tgctatcaaa 300
gcggctggaa atgtcaagag atttttccct tcagaatttg gaaacgacgt tgaccgaacc 360
catgctgtgg aaccagcaaa atctacattt gaaatgaagg ctcaactccg cagaactatt 420
gaggcagaag ggatccctta cacttatgtg tcgtccaatt tctttgccgg ttatttcttg 480
cctgtattgg gacaggtagg agtcactgct ccccctagag acaaagtcac cattttaggg 540
gatgggaatc aaaaggctgt tttcaacaag gaagatgata ttggaacata cacaatccga 600
gctgctgatg atccaagaac attgaataag atcctttaca ttaggcctcc tcggaatacc 660
tactcaatga atgagcttgt tgccctgtgg gagaagaaaa ttggcaaaac tcttgaaaag 720
acttacgttc cagaggagca gcttctaaag aacattcaag aggccgaaat accatggaat 780
gttgtgttag caatcaacca ttccgtcttt gtaaagggtg atcataccaa cttcgcgatc 840
aaaccatctt tcggcgtcga ggcctccgag ctttatcccg atgtcaagta taccactgtt 900
gaggagtacc ttagtcagtt tgtttaa 927
<210> 10
<211> 324
<212> PRT
<213> Pimpinella anisum
<400> 10
Met Gly Ser Ile Glu Gln Lys Ser Arg Ile Leu Val Phe Gly Gly Thr
1 5 10 15
Gly Tyr Ile Gly Asn Phe Ile Val Lys Ala Cys Val Ala Ala Gly His
20 25 30
Pro Thr Tyr Val Tyr Val Arg Pro Met Lys Pro Asp His Asn Pro Ser
35 40 45
Lys Leu Asp Val Leu Asn Glu Tyr Lys Ser Leu Gly Val Thr Ile Phe
50 55 60
Glu Gly Glu Leu Asp Glu His Glu Lys Leu Val Asp Val Leu Arg Gln
65 70 75 80
Val Asp Ile Val Ile Val Thr Leu Ala Ile Pro Gln Cys His Glu Gln
85 90 95
His Lys Ile Ile Glu Ala Met Lys Glu Ala Gly Asn Ile Lys Arg Phe
100 105 110
Ile Pro Ser Glu Phe Gly Asn Asp Val Asp Arg Ile Ser Pro Leu Pro
115 120 125
Pro Phe Gln Glu Gly Val Cys Lys Ile Lys Lys Gly Val Arg Arg Ala
130 135 140
Ala Glu Lys Ser Gly Ile Pro Tyr Thr Phe Val Ser Ser Asn Ser Cys
145 150 155 160
Gly Ala Tyr Phe Val Asn Phe Leu Leu Arg Pro Ser Asp Glu Lys Leu
165 170 175
Arg Lys Val Thr Val Tyr Gly Thr Gly Glu Ala Lys Phe Pro Leu Asn
180 185 190
Tyr Glu Lys Asp Ile Ala Glu Tyr Thr Leu Arg Leu Ala Thr Asp Pro
195 200 205
Arg Ala Ala Asn Ser Leu Val Phe Tyr Arg Pro Pro Lys Asn Ile Val
210 215 220
Ser Gln Leu Asp Leu Ile Ser Ser Trp Glu Lys Lys Thr Gly Arg Thr
225 230 235 240
Leu Glu Lys Thr Tyr Val Ser Glu Glu Glu Ile Ile Lys Leu Ser Gln
245 250 255
Thr Ala Ser Thr Val Gln Asp Ala Val Gly Thr Ser Ile Leu His Ser
260 265 270
Ile Phe Val Lys Gly Glu Gln Met Asn Phe Glu Leu Lys Glu Asp Glu
275 280 285
Leu Glu Val Ser Lys Leu Tyr Pro Asp Tyr Lys Tyr Thr Ser Val Asp
290 295 300
Glu Leu Leu Asp Ile Phe Leu Val Asp Pro Pro Lys Pro Ala Ser Ala
305 310 315 320
Ala Phe Gly
<210> 11
<211> 972
<212> DNA
<213> 人工序列
<400> 11
atgggttcta ttgagcagaa aagcaggata cttgtatttg gaggaaccgg ttatattggt 60
aatttcatag taaaagcatg cgttgcagct ggtcatccaa cttatgttta tgttcgtccg 120
atgaaacctg atcataatcc ctccaagtta gacgttctca acgaatataa atcccttgga 180
gttaccattt tcgagggaga actcgatgaa catgagaagc tcgtggatgt gctccgtcag 240
gtagacatcg ttattgtgac attagcaata cctcaatgcc atgaacaaca caaaataata 300
gaagccatga aagaagctgg caacataaag agatttattc cttcagaatt tggaaatgac 360
gtggatagga ttagtccatt gccaccgttt caagaagggg tctgtaaaat caagaaagga 420
gtcagaaggg ccgctgaaaa atctggaata ccttacactt ttgtttcctc aaactcatgt 480
ggagcatatt ttgttaattt cttgcttcgt ccctctgatg aaaagctccg caaagttact 540
gtctatggga ctggtgaagc taaatttccg ttgaactacg aaaaagacat agctgaatat 600
acactgaggc tcgcaacaga tccacgagca gcaaatagct tggttttcta caggcctcca 660
aagaatatag tctcacagtt agatttgatt tcaagctggg agaaaaaaac tggacgtact 720
ctggaaaaga catacgtctc tgaggaagaa atcatcaagc tctctcagac ggcctctact 780
gtgcaggatg ctgtggggac atccatactt catagcattt tcgtaaaagg tgagcagatg 840
aattttgagc tgaaagagga tgagttagaa gtatctaagc tttatccaga ctacaagtat 900
acatcagttg atgaacttct tgatattttt ctggttgatc caccaaaacc agcatcagct 960
gctttcgggt ag 972
Claims (7)
1.一种丁香酚的微生物合成方法，其特征在于，组合表达松柏醇酰基转移酶CFAT和丁香酚合成酶EGS2，以松柏醇为底物直接合成丁香酚。
2.根据权利要求1所述的丁香酚的微生物合成方法，其特征在于，所述松柏醇酰基转移酶CFAT的氨基酸序列和基因序列分别如SEQ ID No.1和SEQ ID No.2所示，丁香酚合成酶EGS2的氨基酸序列和基因序列分别如SEQ ID No.5和SEQ ID No.6所示。
3.一种丁香酚的微生物合成方法，其特征在于，组合表达松柏醇酰基转移酶CFAT和丁香酚合成酶APS1，以松柏醇为底物直接合成丁香酚。
4.根据权利要求3所述的丁香酚的微生物合成方法，其特征在于，所述松柏醇酰基转移酶CFAT的氨基酸序列和基因序列分别如SEQ ID No.1和SEQ ID No.2所示，丁香酚合成酶APS1的基因序列如SEQ ID No.9所示。
5.一种丁香酚的微生物合成方法，其特征在于，组合表达松柏醇酰基转移酶CFAT和丁香酚合成酶AIS1，以松柏醇为底物直接合成丁香酚。
6.根据权利要求5所述的丁香酚的微生物合成方法，其特征在于，所述松柏醇酰基转移酶CFAT的氨基酸序列和基因序列分别如SEQ ID No.1和SEQ ID No.2所示，丁香酚合成酶AIS1的氨基酸序列和基因序列分别如SEQ ID No.10和SEQ ID No.11所示。
7.松柏醇酰基转移酶CFAT和丁香酚合成酶EGS2或APS1或AIS1组合，以松柏醇为底物，在丁香酚合成中的应用。
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Citations (1)
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| US20100031398A1 (en) * | 2006-07-07 | 2010-02-04 | Washington State University | Genes encoding chavicol/eugenol synthase from the creosote bush larrea tridentata |
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