Citation: Deng Dun, Zhang Yun, Sun Aijun, Sai Ke, Hu Yunfeng. Functional Characterization of a New Antarctic Microbial Esterase EST112-2 and Its Use in the Preparation of Chiral Tertiary Alcohol (S)-Linalool[J]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 1185-1192. doi: 10.6023/cjoc201710019 shu

Functional Characterization of a New Antarctic Microbial Esterase EST112-2 and Its Use in the Preparation of Chiral Tertiary Alcohol (S)-Linalool

Deng Dun ^a,c,d ,
Zhang Yun ^a,c ,
Sun Aijun ^a,c ,
Sai Ke ^b,e,f,, ,
Hu Yunfeng ^a,c,,

a.
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301
b.
Department of Neurosurgery/Neuro-oncology, Sun Yat-sen University Cancer Center, Guangzhou 510060
c.
Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301
d.
Institute of Animal Science, Guangdong Academy of Agricultural Science, Guangzhou 510640
e.
Collaborative Innovation Center for Cancer Medicine, Guangzhou 510060
f.
State Key Laboratory of Oncology in South China, Guangzhou 510060

Corresponding author: Sai Ke, yunfeng.hu@scsio.ac.cn Hu Yunfeng, saike@sysucc.org.cn
Received Date: 17 December 2017
Revised Date: 26 December 2017
Available Online: 18 May 2018
Fund Project: Project supported by the Priority Research Program of the Chinese Academy of Sciences (No. XDA11030404), the Scientific and Technological Project of Ocean and Fishery from Guangdong Province (No. A201701C12), the Guangzhou Science and Technology Plan Projects (No. 201510010012) and the National Natural Science Foundation of China (No. 21302199)the Guangzhou Science and Technology Plan Projects 201510010012the National Natural Science Foundation of China 21302199the Scientific and Technological Project of Ocean and Fishery from Guangdong Province A201701C12the Priority Research Program of the Chinese Academy of Sciences XDA11030404

Figures(4)

Chiral tertiary alcohols (TAs) are key building blocks for the synthesis of many crucial flavor compounds and pharmaceuticals. The two enantiomers of tertiary alcohol, linalool, differ in odor. So, sustainable strategies for the manufacture of optically pure TAs represented by linalool, are highly desirable. But the enzymatic synthesis of chiral tertiary alcohols through kinetic resolution was not easily achieved, possibly because of the steric hindrance from the chemical structures of tertiary alcohols. Herein, we identified and functionally characterized a new microbial esterase EST112-2 from the antarctic sediments and utilized esterase EST112-2 as a green biocatalyst in the synthesis of chiral tertiary alcohol (S)-linalool through asymmetric hydrolysis of racemic linalyl acetate. Parameters such as pH, temperature, co-solvents, substrate concentrations, enzyme loading and reaction time were optimized for the kinetic resolutions. Desired chiral product (S)-linalool was finally obtained with an enantiomeric excess of over 66% and a yield of over 72% after process optimization. The enantiomeric excess of (S)-linalool prepared by esterase EST112-2 was much higher than that from previous reports.
- biocatalysis,
- antarctic microbial esterase,
- kinetic resolution,
- chiral tertiary alcohol,
- (S)-linalool
1. [1]
  (a) Yao, G. ; Haque, S. ; Sha, L. ; Kumaravel, G. ; Wang, J. ; Engber, T. M. ; Whalley, E. T. ; Conlon, P. R. ; Chang, H. ; Kiesman, W. F. ; Petter, R. C. Biorg. Med. Chem. Lett. 2005, 15, 511.
  (b) Friel, D. K. ; Snapper, M. L. ; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 9942.
  (c) Shibasaki, M. ; Kanai, M. Chem. Rev. 2008, 108, 2853.
2. [2]
  Frizzo, C. D.; Santos, A. C.; Paroul, N.; Serafini, L. A.; Dellacassa, E.; Lorenzo, D.; Moyna, P. Braz. Arch. Biol. Technol. 2000, 43, 313. doi: 10.1590/S1516-89132000000300011
3. [3]
  (a) Thompson, A. S. ; Corley, E. G. ; Huntington, M. F. ; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36: 8937.
  (b) Gulick, R. M. ; Ribaudo, H. J. ; Shikuma, C. M. ; Lustgarten, S. ; Squires, K. E. ; Meyer Ⅲ, W. A. ; Acosta, E. P. ; Schackman, B. R. ; Pilcher, C. D. ; Murphy, R. L. ; Maher, W. E. ; Witt, M. D. ; Reichman, R. C. ; Snyder, S. ; Klingman, K. L. ; Kuritzkes, D. R. N. Engl. J. Med. 2004, 350, 1850.
4. [4]
  Ishihara, Y.; Baran, P. S. Synlett 2010, 41, 1733.
5. [5]
  (a) Freires, I. ; Denny, C. ; Benso, B; de Alencar, S. ; Rosalen, P. Molecules 2015, 20, 7329.
  (b) Herman, A. ; Tambor, K., Herman, A. Curr. Microbiol. 2016, 72, 165.
6. [6]
  Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. 1991, 30, 49. doi: 10.1002/(ISSN)1521-3773
7. [7]
  Adrio, J. L.; Demain, A. L. Biomolecules 2014, 4, 117. doi: 10.3390/biom4010117
8. [8]
  (a) Holt, J. ; Arends, I. W. C. E. ; Minnaard, A. J. ; Hanefeld, U. Adv. Synth. Catal. 2007, 349, 1341.
  (b) Kourist, R. ; Bornscheuer, U. T. Appl. Microbiol. Biotechnol. 2011, 91, 505.
  (c) Yan, Q. J. ; Yang, S. Q. ; Duan, X. J. ; Xu, H. B. ; Liu, Y. ; Jiang, Z. Q. J. Mol. Catal. B: Enzym. 2014, 109, 76.
9. [9]
  Pogorevc, M.; Faber, K. J. Mol. Catal. B:Enzym. 2000, 10, 357. doi: 10.1016/S1381-1177(99)00121-6
10. [10]
  (a) Timmis, K. E. Handbook of Hydrocarbon and Lipid Microbiology, Eds. : McGenity, T. J. ; van der Meer, J. R. ; de Lorenzo, V. ; Berlin, Heidelberg, 2010, p. 1099.
  (b) Li, P. Y. ; Chen, X. L. ; Ji, P. ; Li, C, Y. ; Wang, P. ; Zhang, Y. ; Xie, B. B. ; Qin, Q. L. ; Su, H. N. ; Zhou, B. C. ; Zhang, Y. Z. ; Zhang, X. Y. J. Biol. Chem. 2015, 290, 11188.
11. [11]
  (a) Helistö, P. ; Korpela, T. Enzym. Microb. Technol. 1998, 23, 113.
  (b) Kulkarni, N. ; Gadre, R. V. J. Ind. Microbiol. Biotechnol. 2002, 28, 344.
12. [12]
  Fillat, A.; Romea, P.; Urpí, F.; Pastor, F. I. J.; Diaz, P. Appl. Microbiol. Biotechnol. 2014, 98, 4479. doi: 10.1007/s00253-013-5458-9
13. [13]
  Bassegoda, A.; Fillat, A.; Pastor, F. I.; Diaz, P. Appl. Microbiol. Biotechnol. 2013, 97, 8559. doi: 10.1007/s00253-012-4676-x
14. [14]
  Osprian, I.; Steinreiber, A.; Mischitz, M.; Faber, K. Biotechnol. Lett. 1996, 18, 1331. doi: 10.1007/BF00129965
15. [15]
  Pogorevc, M.; Strauss, T. U.; Hayn, M.; Faber, K. Monatsh. Chem. 2000, 131, 639. doi: 10.1007/s007060070092
16. [16]
  Winkler, U. K.; Stuckmann, M. J. Bacteriol. 1979, 138, 663.
17. [17]
  Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294. doi: 10.1021/ja00389a064
1. [1]
  Meng Shan , Yongmei Yu , Mengli Sun , Shuping Yang , Mengqi Wang , Bo Zhu , Junbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781
2. [2]
  Zhaoxin LI , Ruibo WEI , Min ZHANG , Zefeng WANG , Jing ZHENG , Jianbo LIU . Advancements in the construction of inorganic protocells and their cell mimic and bio-catalytical applications. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2286-2302. doi: 10.11862/CJIC.20240235
3. [3]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
4. [4]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
5. [5]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
6. [6]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
7. [7]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
8. [8]
  Ling Tang , Yan Wan , Yangming Lin . Lowering the kinetic barrier via enhancing electrophilicity of surface oxygen to boost acidic oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100345-100345. doi: 10.1016/j.cjsc.2024.100345
9. [9]
  Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
10. [10]
  Manman Ou , Yunjian Zhu , Jiahao Liu , Zhaoxuan Liu , Jianjun Wang , Jun Sun , Chuanxiang Qin , Lixing Dai . Polyvinyl alcohol fiber with enhanced strength and modulus and intense cyan fluorescence based on covalently functionalized graphene quantum dots. Chinese Chemical Letters, 2025, 36(2): 110510-. doi: 10.1016/j.cclet.2024.110510
11. [11]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
12. [12]
  Zongyi Huang , Cheng Guo , Quanxing Zheng , Hongliang Lu , Pengfei Ma , Zhengzhong Fang , Pengfei Sun , Xiaodong Yi , Zhou Chen . Efficient photocatalytic biomass-alcohol conversion with simultaneous hydrogen evolution over ultrathin 2D NiS/Ni-CdS photocatalyst. Chinese Chemical Letters, 2024, 35(7): 109580-. doi: 10.1016/j.cclet.2024.109580
13. [13]
  Yaxin Sun , Huiyu Li , Shiquan Guo , Congju Li . Metal-based cathode catalysts for electrocatalytic ORR in microbial fuel cells: A review. Chinese Chemical Letters, 2024, 35(5): 109418-. doi: 10.1016/j.cclet.2023.109418
14. [14]
  Yiqiao Chen , Ao Liu , Biwen Yang , Zhenzhen Li , Binggang Ye , Zhouyi Guo , Zhiming Liu , Haolin Chen . Photoluminescence and photothermal conversion in boric acid derived carbon dots for targeted microbial theranostics. Chinese Chemical Letters, 2024, 35(9): 109295-. doi: 10.1016/j.cclet.2023.109295
15. [15]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
16. [16]
  Pingping HAO , Fangfang LI , Yawen WANG , Houfen LI , Xiao ZHANG , Rui LI , Lei WANG , Jianxin LIU . Hydrogen production performance of the non-platinum-based MoS₂/CuS cathode in microbial electrolytic cells. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1811-1824. doi: 10.11862/CJIC.20240054
17. [17]
  Yuqing Liu , Yu Yang , Yuhan E , Changlong Pang , Di Cui , Ang Li . Insight into microbial synthesis of metal nanomaterials and their environmental applications: Exploration for enhanced controllable synthesis. Chinese Chemical Letters, 2024, 35(11): 109651-. doi: 10.1016/j.cclet.2024.109651
18. [18]
  Shilong Li , Liang Duan , Qiusheng Gao , Hengliang Zhang . Reduction of methane emission from microbial fuel cells during sulfamethoxazole wastewater treatment. Chinese Chemical Letters, 2025, 36(6): 110997-. doi: 10.1016/j.cclet.2025.110997
19. [19]
  Shunyu Wang , Yanan Zhu , Yang Zhao , Wanli Nie , Hong Meng . Steric effects and electronic manipulation of multiple donors on S₀/S₁ transition of D_n-A emitters. Chinese Chemical Letters, 2025, 36(4): 110555-. doi: 10.1016/j.cclet.2024.110555
20. [20]
  Hongrui Zhang , Miaoying Cui , Yongjie Lv , Yongfang Rao , Yu Huang . A short review on research progress of ZnIn₂S₄-based S-scheme heterojunction: Improvement strategies. Chinese Chemical Letters, 2025, 36(4): 110108-. doi: 10.1016/j.cclet.2024.110108

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1077)
HTML views(177)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142