|本期目录/Table of Contents|

[1]裴朝红,张红蕾,张超,等.一株高效不对称还原产生(R)-苯基乙二醇的菌株筛选、鉴定及全细胞催化体系[J].应用与环境生物学报,2018,24(02):352-356.[doi:10.19675/j.cnki.1006-687x.2017.05011]
 PEI Chaohong,ZHANG Honglei,ZHANG Chao,et al.Screening and identification of bacterial strain producing (R)-1-phenyl-1,2-ethanediol by efficient whole-cell catalytic reduction system[J].Chinese Journal of Applied & Environmental Biology,2018,24(02):352-356.[doi:10.19675/j.cnki.1006-687x.2017.05011]
点击复制

一株高效不对称还原产生(R)-苯基乙二醇的菌株筛选、鉴定及全细胞催化体系()
分享到:

《应用与环境生物学报》[ISSN:1006-687X/CN:51-1482/Q]

卷:
24卷
期数:
2018年02期
页码:
352-356
栏目:
研究论文
出版日期:
2018-04-25

文章信息/Info

Title:
Screening and identification of bacterial strain producing (R)-1-phenyl-1,2-ethanediol by efficient whole-cell catalytic reduction system
作者:
裴朝红张红蕾张超徐志栋 李玮
河北大学化学与环境科学学院 保定 071002
Author(s):
PEI Chaohong ZHANG Honglei ZHANG Chao XU Zhidong LI Wei
College of Chemistry & Environmental Science, Hebei University, Baoding 071002, China
关键词:
红球菌全细胞催化不对称还原α-羟基苯乙酮(R)-苯基乙二醇
Keywords:
Rhodococcus sp. whole-cell biocatalyst asymmetric reduction α-hydroxyacetophenone (R)-1-phenyl-1 2-ethanediol
分类号:
Q939.97 : TQ920
DOI:
10.19675/j.cnki.1006-687x.2017.05011
摘要:
R)-苯基乙二醇是合成许多光学活性药物的重要手性中间体,其制备具有重要的现实意义. 以α-羟基苯乙酮为底物,从土壤中筛选得到一株能够立体选择性催化α-羟基苯乙酮产生(R)-苯基乙二醇的细菌菌株HBU-SI7. 经形态学观察和16S rDNA序列分析,鉴定此转化菌株为红球菌属菌株Rhodococcus sp. 菌株全细胞催化体系研究表明在邻苯二甲酸二丁酯-磷酸盐缓冲液(V:V = 1:3)的两相催化体系下,菌体转化α-羟基苯乙酮的最优浓度为3.0 g/L,转化率高达96.2%,e.e值为99.3%. 本研究建立的红球菌全细胞催化还原体系对(R)-苯基乙二醇的高效制备具有潜在的研究和应用价值. (图6 表2 参20)
Abstract:
(R)-1-Phenyl-1,2-ethanediol [(R)-PED] is an important chiral intermediate used to synthesize pharmaceutical intermediates. The production of (R)-PED is of great practical significance. A novel bacterial strain HBU-SI7 isolated from soil samples was screened using α-hydroxyacetophenone (2-HAP) as substrate, which is capable of enantioselective reduction of 2-HAP to (R)-PED. HBU-SI7 was identified as Rhodococcus sp. by bacterial morphological observation and 16S rDNA analysis. The analysis of whole-cell catalytic system showed that the bioconversion of 2-HAP reached 96.2% in the two-phase reaction system (dibutyl phthalate/phosphate buffer = 1/3, V/V) with the substrate concentration of 3.0 g/L, and 99.3% of e.e. for (R)-PED was achieved. A new enantioselective reduction system with the whole cells of Rhodococcus sp. was established for efficient production of (R)-PED, which has potential research and application values.

参考文献/References:

1. Ni Y, Xu JH. Biocatalytic ketone reduction: a green and efficient access to enantiopure alcohols [J]. Biotechnol Adv, 2012, 30 (6): 1279-1288
2. Pollard DJ, Woodley JM. Biocatalysis for pharmaceutical intermediates: the future is now [J]. Trends Biotechnol, 2007, 25 (2): 66-73
3. Liu JY, Lin YP, Qiu H, Morisseau C, Rose TE, Hwang SH, Chiamvi-monvat N, Hammock BD. Substituted phenyl groups improve the pharmacokinetic profile and anti-inflammatory: effect of urea-based soluble epoxide hydrolase inhibitors in murine models [J]. Eur J Pharma Sci, 2013, 20 (1): 1-9
4. Cao L, Lee J, Chen W, Wood TK. Enantioconvergent production of (R)-1-phenyl-1,2-ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases [J]. Biotechnol Bioeng, 2006, 94 (3): 522-529
5. Kumar P, Upadhyay RK, Pandey RK. Asymmetric dihydroxylation route to (R)-isoprenaline, (R)-norfluoxetine and (R)-fluoxetine [J]. Tetrahedron Asymmetry, 2004, 15 (24): 3955-3959
6. Pandey RK, Fernandes RA, Kumar P. An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine [J]. Tetrahedron Lett, 2002, 43 (25): 4425-4426
7. Oda S, Kikuchi Y, Nanishi Y. Synthesis of optically-active mandelic acid via microbial oxidation of racemic 1-phenyl-1,2-ethanediol [J]. Biosci Biotechnol Biochem, 1992, 56 (8): 1216-1220
8. 张之建, 李鸣海, 张耀华, 巢向红, 陈敖, 刘可可, 管芹芹. 脂肪酶Novozyme435手性拆分(R,S)-扁桃酸[J]. 国外医药(抗生素分册), 2016, 37 (2): 81-83 [Zhang ZZ, Li HM, Zhang YH, Chao XH, Chen A, Liu KK, Guan QQ. The chiral separation of mandelic acid by lipase novozyme 435 [J]. World Notes Antibiot, 2016, 37 (2): 81-83]
9. Blagam B, Mitra R, Richardson DE. Osmium-catalyzed asymmetric dihydroxylstion by carbon dioxide-activated hydron peroxide and N-methylmorpholine [J]. Tetrahedron Lett, 2008, 49: 1071-1075
10. Lee DM, Kwak SH, Lee KI. Highly enantioselective Rh-catalyzed transfer hydrogenation of α-functionalized arylketones [J]. Bull Korean Chem Soc, 2009, 30 (6): 1317-1324
11. Gruber CC, Lavandera I, Faber K, Kroutil W. From a racemate to a single enantiomer: deracemization by stereoinversion [J]. Adv Synth Catal, 2007, 348 (2): 1789-1805
12. Annemarie H, Daniёlle GIP, Jim A. Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: complementary approaches [J]. Tetrahedron Asymmetry, 2001, 12: 1025-1034
13. Matsuyama A, Yamamoto H, Kawada N. Industrial Production of (R)-1,3-butanediol by new biocatalysts [J]. J Mol Catal B Enzym, 2001, 11: 513-518
14. Kazici HC, Bayraktar E, Mehmetoglu U. Optimization of the asymmetric synthesis of chiral aromatic alcohol using freeze-dried carrots as whole-cell biocatalysts [J]. Green Process Synth, 2016, 5 (2): 131-137
15. Wei P, Gao JX, Zheng GW, Wu H, Zong MH, Lou WY. Engineering of a novel carbonyl reductase with coenzyme regeneration in E. coli for efficient biosynthesis of enantiopure chiral alcohols [J]. J Biotechnol, 2016, 68: 54-62
16. Cui ZM, Zhang JD, Fan XJ, Zheng GW, Chang HH, Wei WL. Highly efficient bioreduction of 2-hydroxyacetophenone to (S)- and (R)-1-phenyl-1,2-ethanediol by two substrate tolerance carbonyl reductases with cofactor regeneration [J]. J Biotechnol, 2017, 243: 1-9
17. 陈海波. 酵母催化苯基乙二醇衍生物的不对称合成[D]. 无锡: 江南大学, 2011 [Chen HB. Asymmeric synthesis of 1-phenyl-1,2-ethanediol derivatives catalyzed by baker’’s yeast [D]. Wuxi: Jiangnan University, 2011]
18. Hu QS, Xu Y, Nie Y. Highly enantioselective reduction of 2-hydroxy-1-phenylethanone to enantiopure (R)-phenyl-1,2-ethanediol using Saccharomyces cerevisiae of remarkable reaction stability [J]. Bioresour Technol, 2010, 101 (22): 8502-8508
19. Zhang RZ, Zhou RZ, Xu Y, Liang HB, Jiang JW, Xiao R. Coupled (R)-carbonyl reductase and glucose dehydrogenase catalyzes (R)-1-phenyl-1, 2-ethanediol biosynthesis with excellent stereochemical selectivity [J]. Process Biochem, 2015, 50: 1807-1813
20. Pollard DJ, Woodley JM. Biocatalysis for pharmaceutical intermediates: the future is now [J]. Trends Biotechnol, 2007, 25 (2): 66-73
21. Zhao H, Wang XL, Zhang HL, Li CD, Wang SY. Production of dihydrodaidzein and dihydrogenistein by a novel oxygen-tolerant bovine rumen bacterium in the presence of atmospheric oxygen [J]. Appl Microbiol Biotechnol, 2011, 92 (4): 803-813
a) 梅建凤, 陈虹, 王鸿, 应国清, 易瑜. 水/有机溶剂两相体系中生物转化合成2-苯乙醇[J]. 化学反应工程与工艺, 2009, 25 (1): 69-73 [Mei JF, Chen H, Wang H, Ying GQ, Yi Y. Synthesis of 2-phenylethanol by bioconversion in aqueous/organic solvent two-phase system [J]. Chem React Eng Technol, 2009, 25 (1): 69-73]

相似文献/References:

[1]郭娜,李志敏,叶勤.烷烃降解菌的筛选、鉴定及优势菌株的降解特性[J].应用与环境生物学报,2011,17(04):572.[doi:10.3724/SP.J.1145.2011.00572]
 GUO Na,LI Zhimin,YE Qin.Screen and Identification of Alkane Degrading Bacteria and Characteristics of a Predominant Strain[J].Chinese Journal of Applied & Environmental Biology,2011,17(02):572.[doi:10.3724/SP.J.1145.2011.00572]
[2]孙纪全,徐莲,汤岳琴,等.红球菌Chr-9降解吡啶和苯酚的特性[J].应用与环境生物学报,2012,18(04):647.[doi:10.3724/SP.J.1145.2012.00647]
 SUN Jiquan,XU Lian,TANG Yueqin,et al.Degradation Characteristics of Pyridine and Phenol by Rhodococcus sp. Chr-9[J].Chinese Journal of Applied & Environmental Biology,2012,18(02):647.[doi:10.3724/SP.J.1145.2012.00647]
[3]郭倩,张铁雨,冯进辉,等.高效转化胆固醇菌株的筛选、鉴定及转化条件优化[J].应用与环境生物学报,2014,20(01):101.[doi:10.3724/SP.J.1145.2014.00101]
 GUO Qian,ZHANG Tieyu,FENG Jinhui,et al.Screening, identification and condition optimization of a bacterial strain efficient in biotransforming cholesterol[J].Chinese Journal of Applied & Environmental Biology,2014,20(02):101.[doi:10.3724/SP.J.1145.2014.00101]
[4]王旭昌 宗红,陆信曜,诸葛斌,等.醋酸杆菌生物催化丙烯醛合成丙烯酸[J].应用与环境生物学报,2015,21(04):652.[doi:10.3724/SP.J.1145.2014.12021]
 WANG Xuchang,ZONG Hong,LU Xinyao,et al.Biosynthesis of acrylic acid from acrolein by Acetobacter sp.[J].Chinese Journal of Applied & Environmental Biology,2015,21(02):652.[doi:10.3724/SP.J.1145.2014.12021]
[5]杨智,陈吉祥,秦波,等.3株石油降解红球菌(Rhodococcus spp.)特性及相关基因分析[J].应用与环境生物学报,2015,21(05):805.[doi:10.3724/SP.J.1145.2015.01063]
 YANG Zhi,CHEN Jixiang,QIN Bo,et al.Characterization and catabolic genes detection of three oil-degrading Rhodococcus spp.[J].Chinese Journal of Applied & Environmental Biology,2015,21(02):805.[doi:10.3724/SP.J.1145.2015.01063]

更新日期/Last Update: 2018-04-25