CN107418981B - 白地霉菌株不对称催化还原卤代芳香酮的方法 - Google Patents
白地霉菌株不对称催化还原卤代芳香酮的方法 Download PDFInfo
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- 239000008103 glucose Substances 0.000 claims description 5
- ZDOYHCIRUPHUHN-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanone Chemical group CC(=O)C1=CC=CC=C1Cl ZDOYHCIRUPHUHN-UHFFFAOYSA-N 0.000 claims description 3
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- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 claims description 3
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 claims description 2
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- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000001540 sodium lactate Substances 0.000 claims description 2
- 229940005581 sodium lactate Drugs 0.000 claims description 2
- 235000011088 sodium lactate Nutrition 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims 6
- 210000004027 cell Anatomy 0.000 claims 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 210000001082 somatic cell Anatomy 0.000 claims 1
- 150000008062 acetophenones Chemical class 0.000 abstract description 3
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical class OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract description 2
- 244000168141 Geotrichum candidum Species 0.000 description 16
- 239000000047 product Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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Abstract
白地霉菌株不对称催化还原卤代芳香酮的方法,涉及生物催化领域,包括如下步骤:(1)往白地霉菌体细胞中加入缓冲溶液至白地霉菌体细胞浓度为0.2~0.3g/ml,调pH为6.8~7.2,加共底物至浓度为3~8%(w/v);(2)加入底物卤代芳香酮至浓度为6.67mmol/L~16.7mmol/L,在温度20~30℃的条件下反应至少24h,即可。采用本发明白地霉菌株在本发明转化条件下,能够高效地将卤代苯乙酮转化成(S)‑卤代苯乙醇,转化率高达99%,转化获得的产物纯度(产物e.e.值)大于99%,工业应用前景良好。
Description
技术领域
本发明涉及生物催化领域,具体涉及白地霉菌株不对称催化还原卤代芳香酮的方法。
背景技术
光学手性醇是合成手性药物、精细化学品、农药品及液晶材料等的重要中间体。随着环境污染的日益加剧和石油资源的日益枯竭,以可再生的物质资源为原料,以高效专一,绿色节能为特征的生物催化过程将越来越受到关注。对海洋来源微生物作为生物催化剂应用于有机合成的研究在全世界范围内都属于一个新兴领域,与从常规来源分离的酶相比,海洋微生物在极端条件(即极端温度,压力,pH或有机溶剂)下产生具有高稳定性和活性的新型酶,其应广泛用于生物催化生产精细化学品。
目前,生物催化法制备手性芳香酮的相关报道较多,但仍然无法实现工业化生产,主要原因是生产菌株催化活性不稳定、产物积累量不高及立体选择性较差。
中国专利CN99125752.9一种白地霉G702(Geotrichum sp.702)菌株,系从土壤中筛选出并经沙氏斜面上生长良好的菌体在培养液中培养二天获得纯的菌株。该菌株具有高还原活力,可选择性还原酮得到S-型手性醇化合物。但是白地霉G702(Geotrichum sp.702)菌株还原芳香酮的转化率较低,对于卤代芳香酮的还原立体选择性和转化率均较低。
发明内容
本发明的目的是提供一种或几种海洋来源的白地霉菌株不对称催化还原卤代芳香酮的方法。
白地霉菌株不对称催化还原卤代芳香酮的方法,包括如下步骤:
(1)往白地霉菌体细胞中加入缓冲溶液至白地霉菌体细胞浓度为0.2~0.3g/ml,调pH为6.8~7.2,加共底物至浓度为3~8%(w/v);
(2)加入底物卤代芳香酮至浓度为6.67mmol/L~16.7mmol/L,在温度20~30℃的条件下反应至少24h,即可。
进一步地,步骤(1)中,所述白地霉菌体为Geotrichumcandidum GIM 2.361或Geotrichumcandidum GIM 2.616;
进一步地,所述共底物可为葡萄糖、乳酸钠。
进一步地,步骤(1)中,所述菌体细胞的浓度为0.25g/ml。
进一步地,步骤(1)中,调节pH为7.0。
进一步地,步骤(1)中,所述共底物的浓度为5%(w/v)。
进一步地,步骤(2)中,所述卤代芳香酮为溴代苯乙酮或氯代苯乙酮,优选邻氯苯乙酮、间氯苯乙酮、对氯苯乙酮、
进一步地,步骤(2)中,所述底物卤代芳香酮的浓度为10mmol/L。
进一步地,步骤(2)中,所述反应温度为25℃。
进一步地,步骤(2)中,所述反应的时间为24h。
采用本发明白地霉菌株在本发明转化条件下,能够高效地将卤代苯乙酮转化成(S)-卤代苯乙醇,转化率高于90%,转化获得的产物纯度(产物e.e.值)大于95%,优选高于99%,工业应用前景良好。
具体实施方式
为了使本领域的技术人员更好地理解本发明的技术方案,下面进一步披露一些非限制实施例对本发明作进一步的详细说明。
实施例1
1.1仪器与试剂
LC1620高效液相色谱[正相手性柱:Ultimate Cellu-D,4.6x250mm,5μm];MS-100恒温混匀仪;Anton Paar型旋光仪MCP200;PHS-3C型PH计;Bruker400M核磁共振仪,湘仪L530离心机,柱层析硅胶200-300目;50mL离心管
Geotrichumcandidum GIM 2.361,Geotrichumcandidum GIM 2.616购买于广东省微生物菌种保藏中心
1.2菌的活化及培养
用无菌吸管吸取0.3-0.5毫升适宜的液体培养基(葡萄糖1%,蛋白胨1%,酵母提取物0.5%,琼脂2%)滴入安瓿瓶内,轻轻震荡,使冻干菌体溶解呈悬浮状,吸取全部菌悬液,移植于培养基平板上,活化,挑菌落于1L的锥形瓶中加入500mL蒸馏水,葡萄糖7.5g,蛋白胨2.5g,酵母膏2.5g,Na2HPO4 0.25g,NaH2PO4 0.25g,MgSO4 0.25g,NaCl 0.5g的液体培养基中,在摇床中恒温28℃,转速180rmp将该培养物在相互摇动约96小时。通过在4000rpm和4℃的条件下离心20分钟收集细胞,或通过过滤袋过滤。除去上清液,并用Na2HPO4-KH2PO4缓冲液(100mM,pH7.0)冲洗细胞并再次离心,弃去上清液,将颗粒保存在-20℃。
1.3海洋真菌催化芳香酮的不对称还原
取2-3g全细胞于50mL的离心管中,加入0.5g葡萄糖,10mLNa2HPO4-KH2PO4缓冲溶液(pH=7)再加入10mM底物置于摇床中在25℃,220rmp的条件下进行反应24h后取出,离心,取2mL上清液用2mL正己烷:异丙醇=95:5的流动相进行萃取,离心,萃取液用无水Na2SO4干燥。对于空白反应,设置是相同的,但没有添加细胞。允许反应在给定温度下进行24小时。为了处理,通过离心除去细胞,并用NaCl饱和2mL上清液,然后用2×1mL HPLC洗脱液(正己烷/i-PrOH=95/5,v/v)萃取,摇动5分钟。将合并的有机层用Na2SO4干燥并通过HPLC测定产率和ee值。
1.4分析与检测
通过使用Shimadzu LC-10AT VP系列和Shimadzu SPD-M10Avp光电二极管阵列检测器(190~370nm)的AD-H柱(洗脱液:正己烷/正己烷/i-PrOH(95:5,v/v),流速:0.5mL/min,柱温25℃)。根据以下保留时间数据(如表1所示),通过手性HPLC分析测定分析物的产量及ee值,结果见表2。
表1:
序号 | 底物 | 底物出峰时间 | 产物出峰时间 |
1 | 对氯苯乙酮 | 10.78min | tR(R)=15.09min;tR(S)=16.09min |
2 | 对溴苯乙酮 | 11.21min | tR(R)=16.83min;tR(S)=17.99min |
3 | 间氯苯乙酮 | 10.49min | tR(R)=14.60min;tR(S)=16.35min |
4 | 邻氯苯乙酮 | 10.71min | tR(R)=13.32min;tR(S)=13.98min |
产率=(CS+CR)/C0×100%
ee=(CS-CR)/(CS+CR)×100%
表2:
由表2可以看出:采用Geotrichumcandidum GIM 2.361和GeotrichumcandidumGIM 2.616催化还原卤代苯乙酮,转化率全部达90%以上,产物纯度(产物e.e.值)大于95%,产物构型为S构型。
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。
Claims (9)
1.白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于包括如下步骤:
(1)往白地霉菌体细胞中加入缓冲溶液至白地霉菌体细胞浓度为0.2~0.3g/ml,调pH为6.8~7.2,加共底物至浓度为3~8%( w/v );
(2)加入底物卤代芳香酮至浓度为6.67mmol/L~16.7mmol/L,在温度20~30℃的条件下反应至少24h,即可;
所述白地霉菌体为Geotrichumcandidum GIM 2.361或Geotrichum-candidum GIM2.616。
2.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于所述共底物为葡萄糖、乳酸钠。
3.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于步骤(1)中,所述菌体细胞的浓度为0.25g/ml。
4.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于步骤(1)中,调节pH为7.0。
5.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于步骤(1 )中,所述共底物的浓度为5%( w/v )。
6.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于步骤(2)中,所述卤代芳香酮为溴代苯乙酮或氯代苯乙酮。
7.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于所述卤代芳香酮为邻氯苯乙酮、间氯苯乙酮或对氯苯乙酮。
8.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于步骤(2)中,所述底物卤代芳香酮的浓度为10 mmol/L。
9.如权利要求1所述白地霉菌株不对称催化还原卤代芳香酮的方法,其特征在于步骤(2)中,所述反应温度为25℃、反应的时间为24h。
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CN103642849A (zh) * | 2013-12-12 | 2014-03-19 | 天津市食品加工工程中心 | 一种不对称还原1-萘乙酮为光学纯(s)-1-萘基-1-乙醇的方法及筛选方法 |
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