Enantioselective Resolution of (±)-1-Phenylethyl Acetate by Using the Whole Cells of Deep-sea Bacterium Bacillus sp. DL-2

doi:10.1007/s40242-019-9126-1

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (5): 792-798.doi: 10.1007/s40242-019-9126-1

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Enantioselective Resolution of (±)-1-Phenylethyl Acetate by Using the Whole Cells of Deep-sea Bacterium Bacillus sp. DL-2

DONG Lu^1,2,3, XU Yongkai⁴, ZHANG Yun^1,3, SUN Aijun^1,3, HU Yunfeng^1,3

1. CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China;
3. Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, P. R. China;
4. Affiliated Hospital of Shandong University of Traditional Chinese Medicine, Jinan 250014, P. R. China

Received:2019-04-30 Online:2019-10-01 Published:2019-09-24
Contact: HU Yunfeng E-mail:yunfeng.hu@scsio.ac.cn
Supported by:
Supported by the Natural Science Foundation of Guangdong Province, China(No.2018A030313151), the Senior User Project of the Research Vessel KEXUE(No.KEXUE2018G05), the Priority Research Program of the Chinese Academy of Sciences(No.XDA11030404) and the Scientific and Technological Project of the Ocean and Fishery from Guangdong Province, China(No.A201701C12).

Abstract

Abstract: Bacillus sp. DL-2 was isolated from the deep sea of the Western Pacific and further utilized as novel biocatalysts to efficiently asymmetrically hydrolyze (±)-1-phenylethyl acetate. After the optimization of hydrolytic reactions, chiral chemicals (R)-1-phenylethanol and (S)-1-phenylethyl acetate were obtained with high optical purities (96% and 99.8%, respectively). Our research is about the asymmeric hydrolysis of (±)-1-phenylethyl acetate using whole-cell biocatalysts. In addition, the optical purity of (S)-1-phenylethyl acetate generated through the kinetic resolution of (±)-1-phenylethyl acetate using the whole-cells of Bacillus sp. DL-2 was the highest report so far. Using the whole cells of deep sea bacterium Bacillus sp. DL-2 as the biocatalysts is an environmentally friendly method and will play critical roles in industrial asymmetric synthesis.

Key words: Deep-sea microorganism, Whole-cell biocatalyst, Asymmetric hydrolysis, (R)-1-Phenylethanol, (S)-1-Phenylethyl acetate

DONG Lu, XU Yongkai, ZHANG Yun, SUN Aijun, HU Yunfeng. Enantioselective Resolution of (±)-1-Phenylethyl Acetate by Using the Whole Cells of Deep-sea Bacterium Bacillus sp. DL-2[J]. Chemical Research in Chinese Universities, 2019, 35(5): 792-798.

References

[1] Huisman G. W., Gray D., Current Opinion in Biotechnology, 2002, 13(4), 352
[2] Pollard D. J., Woodley J. M., Trends in Biotechnology, 2007, 25(4), 66
[3] Yu H. L., Xu J. H., Lu W. Y., Lin G. Q., Advances in Biochemical Engineering/Biotechnology, 2009, 113, 1
[4] Wohlgemuth R., Current Opinion in Microbiology, 2010, 13(3), 283
[5] Zheng G. W., Xu J. H., Current Opinion in Biotechnology, 2011, 22(6), 784
[6] Tibrewal N., Tang Y., Annual Review of Chemical & Biomolecular Engineering, 2014, 5(1), 347
[7] Carvalho A. C. L. D. M., Fonseca T. D. S., Mattos M. C. D., Oliveira M. D. C. F. D., Lemos T. L. G. D., Molinari F., Romano D., Serra I., International Journal of Molecular Sciences, 2015, 16(12), 29682
[8] Kisukuri C. M., Andrade L. H., Organic & Biomolecular Chemistry, 2015, 13, 10086
[9] Kataoka M., Miyakawa T., Shimizu S., Tanokura M., Applied Microbiology & Biotechnology, 2016, 100(13), 5747
[10] Tufvesson P., Lima-Ramos J., Nordblad M., Woodley J. M., Organic Process Research & Development, 2011, 15, 266
[11] Shu Z. Y., Wu J. G., Cheng L. X., Chen D., Jiang Y. M., Li X., Huang J. Z., Applied Biochemistry & Biotechnology, 2012, 166, 536
[12] Marchand P., Lamare S., Legoy M. D., Goubet I., Biotechnology & Bioengineering, 2009, 103(4), 687
[13] Duetz W. A., van Beilen J. B., Witholt B., Current Opinion in Biotechnology, 2001, 12(4), 419
[14] Hudlicky T., Reed J. W., Chemical Society Reviews, 2009, 38(11), 3117
[15] Jin Z., Han S. Y., Zhang L., Zheng S. P., Wang Y., Lin Y., Bioresource Technology, 2013, 130(2), 102
[16] Parages M. L., Gutiérrez-Barranquero J. A., Reen F. J., Dobson A. D. W., O'Gara F., Marine Drugs, 2016, 14(62), 1
[17] Habulin M., Knez Z., Journal of Molecular Catalysis B:Enzymatic, 2009, 58(1), 24
[18] Ma L., Liu X. M., Li D. G., Zhang Z. H., Advanced Materials Research, 2011, 236-238, 981
[19] Liang J. Y., Zhang Y., Sun A. J., Deng D., Hu Y. F., Applied Biochemistry & Biotechnology, 2016, 178(3), 558
[20] Şahin E., Dertli E., Chemistry & Biodiversity, 2017, 14(9), 1
[21] Weber N., Gorwa-grauslund M., Carlquist M., Microbial Cell Factories, 2014, 13(1), 1
[22] Gao W. Y., Fan H. Y., Chen L. F., Wang H. L., Wei D. Z., Biotechnology Letters, 2016, 38(7), 1165
[23] Matsumoto T., Ito M., Fukuda H., Kondo A., Applied Microbiology & Biotechnology, 2004, 64(4), 481
[24] Kaieda M., Nagayoshi M., Hama S., Kondo A., Fukuda H., Applied Microbiology & Biotechnology, 2004, 65(3), 301
[25] Lee S. H., Choi J. I., Han M. J., Choi J. H., Lee S. Y., Biotechnology & Bioengineering, 2005, 90(2), 223
[26] Chen C. S., Fujimoto Y., Girdaukas G., Sih C. J., Journal of the American Chemical Society, 1982, 104, 7294

Enantioselective Resolution of (±)-1-Phenylethyl Acetate by Using the Whole Cells of Deep-sea Bacterium Bacillus sp. DL-2

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