Citation: Hui-Jiao Wen, Qing Chen, Guo-Jun Zheng. Enantioselective synthesis of (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B[J]. Chinese Chemical Letters, ;2015, 26(11): 1431-1434. doi: 10.1016/j.cclet.2015.07.005 shu

Enantioselective synthesis of (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B

1.
State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing 100029, China

Corresponding author: Guo-Jun Zheng,
Received Date: 15 April 2015
Available Online: 24 June 2015

An efficient biocatalytic process has been developed to obtain optically pure (1S,4R)-N-(benzylcarbamoyl)- 4-aminocyclopent-2-en-1-ol which can be used as the key intermediate of ticagrelor. In this research, several N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol derivatives have been investigated in which Candida antarctica lipase B (CALB) was used to catalyze the asymmetric hydrolysis reaction. As expected, some of these substrates successfully gave (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent- 2-en-1-ol in >98% enantiomeric excess (ee) with conversion yields up to 45%.
- N-(Benzylcarbamoyl)-4-aminocyclopent-2-
1. [1]
  [1] F. Burlina, A. Favre, J.L. Fourrey, M. Thomas, An expeditious route to carbocyclic nucleosides: (61)-aristeromycin and (61)-carbodine, Bioorg. Med. Chem. Lett. 7 (1997) 247-250.
2. [2]
  [2] K.H. Park, H. Rapoport, Enantioselective synthesis of (1R,4S)-1-amino-4-(hydroxymethyl)- 2-cyclopentene, a precursor for carbocyclic nucleoside synthesis, J. Org. Chem. 59 (1994) 394-399.
3. [3]
  [3] B.M. Trost, D. Stenkamp, S.R. Pulley, An enantioselective synthesis of cis-4-tertbutoxycarbamoyl- 1-methoxycarbonyl-2-cyclopentene—a useful, general building block, Chem. A: Eur. J. 1 (1995) 568-572.
4. [4]
  [4] T. Ando, K. Kojima, P. Chahota, et al., Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase, Bioorg. Med. Chem. Lett. 18 (2008) 2615-2618.
5. [5]
  [5] N.G. Ramesh, A.J. Klunder, B. Zwanenburg, Enantioselective synthesis of 4-acetylaminocyclopent- 2-en-1-ols from tricyclo[5.2.1.0(2, 6)]decenyl enaminones. Precursors for 5'-norcarbocyclic nucleosides and related antiviral compounds, J. Org. Chem. 64 (1999) 3635-3641.
6. [6]
  [6] P.F. Vogt, J.G. Hansel, M.J. Miller, Asymmetric synthesis of an important precursor to 5'-nor carbocyclic nucleosides, Tetrahedron Lett. 38 (1997) 2803-2804.
7. [7]
  [7] D. Zhang, A. Ghosh, C. Suling, et al., Efficient functionalization of acylnitroso cycloadducts: application to the syntheses of carbocyclic nucleoside precursors, Tetrahedron Lett. 37 (1996) 3799-3802.
8. [8]
  [8] J.J.J. Van Giezen, L. Nilsson, P. Berntsson, et al., Ticagrelor binds to human P₂Y (12) independently from ADP but antagonizes ADP-induced receptor signaling and platelet aggregation, J. Thromb. Haemostasis. 7 (2009) 1556-1565.
9. [9]
  [9] B. Springthorpe, A. Bailey, P. Barton, From ATP to AZD6140: the discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis, Bioorg. Med. Chem. Lett. 17 (2007) 6013-6018.
10. [10]
  [10] M. Arita, K. Adachi, Y. Ito, et al., Enantioselective synthesis of the carbocyclic nucleosides (-)-aristeromycin and (-)-neplanocin A by a chemicoenzymatic approach, J. Am. Chem. Soc. 105 (1983) 4049-4055.
11. [11]
  [11] M. Ikbal, C. Cerceau, F. Le Goffic, et al., Synthè se des deux énantiomè res de l'analogue carbocyclique du nicotinamide ribose et évaluation de leurs proprié té s biologiques, Eur. J. Med. Chem. 24 (1989) 415-420.
12. [12]
  [12] S. Saul, S. Corr, J. Micklefield, Biotransformations in low-boiling hydrofluorocarbon solvents, Angew. Chem. Int. Ed. 43 (2004) 5519-5523.
13. [13]
  [13] J. Dauvergne, A.M. Happe, V. Jadhav, et al., Synthesis of 4-azacyclopent-2-enones and 5,5-dialkyl-4-azacyclopent-2-enones, Tetrahedron 60 (2004) 2559-2567.
14. [14]
  [14] C.R. Johnson, S.J. Bis, Enzymatic asymmetrization of meso-2-cycloalken-1 4-diols and their diacetates in organic and aqueous media, Tetrahedron Lett. 33 (1992) 7287-7290.
15. [15]
  [15] D. Zhang, M.J. Miller, Total synthesis of (±) carbocyclic polyoxin C and its α-epimer, J. Org. Chem. 63 (1998) 755-759.
16. [16]
  [16] M.J. Mulvihill, J.L. Gage, M.J. Miller, Enzymatic resolution of aminocyclopentenols as precursors to D-and L-carbocyclic nucleosides, J. Org. Chem. 63 (1998) 3357-3363.
17. [17]
  [17] E.M. Anderson, K.M. Larsson, O. Kirk, One biocatalyst - many applications: the use of Candida antarctica B-lipase in organic synthesis, Biocatal. Biotransform. 16 (1998) 181-204.
18. [18]
  [18] L. Bollans, J. Bacsa, J.A. Iggo, et al., The acyl nitroso Diels-Alder (ANDA) reaction of sorbate derivatives: an X-ray and 15N NMR study with an application to aminoacid synthesis, Org. Biomol. Chem. 7 (2009) 4531-4538.
19. [19]
  [19] Compound 2: ¹H NMR (400 MHz, CDCl₃): δ 7.47-7.09 (m, 5H), 5.97 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.85 (m, 1H), 4.76 (m, 1H), 2.84 (m, 1H), 2.30 (t, 2H), 1.56 (m, 1H), 1.17 (t, 3H). Compound 3: ¹H NMR (400 MHz, CDCl3): d 7.61-7.24 (m, 5H), 5.98 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.83 (m, 1H), 4.69 (m, 1H), 2.97-2.65 (m, 1H), 2.29 (t, 2H), 1.70-1.48 (m, 3H), 0.98 (t, 3H). Compound 4: ¹H NMR (400 MHz, CDCl3): δ 7.94-7.13 (m, 10H), 6.01 (m, 2H), 5.72 (s, 1H), 5.11 (s, 2H), 4.85(m, 1H), 4.75 (m, 1H), 2.97-2.85 (m, 1H), 1.65 (m, 1H).
20. [20]
  [20] L. Werner, J.R. Hudlicky, M. Wernerova, et al., Synthesis of 1,2-and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines, Tetrahedron 66 (2010) 3761-3769.
21. [21]
  [21] Analytical HPLC methods: the enantiomeric excess analysis was performed using a HPLC system (Shimadzu, Japan) equipped with a CHIRALPAK IF column (0.46 mm × 250 mm × 5 mm), elution with ethanol/hexane 15:85 v/v for compound 1, ethanol/hexane 25:75 v/v for compounds 2 and 3, ethanol/hexane 30:70 for compound 4.
1. [1]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
2. [2]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
3. [3]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
4. [4]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
5. [5]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
6. [6]
  Jiajun Wang , Guolin Yi , Shengling Guo , Jianing Wang , Shujuan Li , Ke Xu , Weiyi Wang , Shulai Lei . Computational design of bimetallic TM₂@g-C₉N₄ electrocatalysts for enhanced CO reduction toward C₂ products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050
7. [7]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
8. [8]
  Zhi Zhu , Xiaohan Xing , Qi Qi , Wenjing Shen , Hongyue Wu , Dongyi Li , Binrong Li , Jialin Liang , Xu Tang , Jun Zhao , Hongping Li , Pengwei Huo . Fabrication of graphene modified CeO2/g-C3N4 heterostructures for photocatalytic degradation of organic pollutants. Chinese Journal of Structural Chemistry, 2023, 42(12): 100194-100194. doi: 10.1016/j.cjsc.2023.100194
9. [9]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
10. [10]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
11. [11]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
12. [12]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
13. [13]
  Zhijie Zhang , Xun Li , Huiling Tang , Junhao Wu , Chunxia Yao , Kui Li . Cs₂CuBr₄ perovskite quantum dots confined in mesoporous CuO framework as a p-n type S-scheme heterojunction for efficient CO₂ photoconversion. Chinese Chemical Letters, 2024, 35(11): 109700-. doi: 10.1016/j.cclet.2024.109700
14. [14]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
15. [15]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
16. [16]
  Xin Jiang , Han Jiang , Yimin Tang , Huizhu Zhang , Libin Yang , Xiuwen Wang , Bing Zhao . g-C₃N₄/TiO_2-X heterojunction with high-efficiency carrier separation and multiple charge transfer paths for ultrasensitive SERS sensing. Chinese Chemical Letters, 2024, 35(10): 109415-. doi: 10.1016/j.cclet.2023.109415
17. [17]
  Dai-Huo Liu , Ao Wang , Hong-Yan Lü , Xing-Long Wu , Dan Luo , Wen-Hao Li , Jin-Zhi Guo , Haozhen Dou , Qianyi Ma , Zhongwei Chen . In situ constructing (MnS/Mn₂SnS₄)@N,S-ACTs heterostructure with superior Na/Li-storage capabilities in half-cells and pouch full-cells. Chinese Chemical Letters, 2024, 35(11): 109285-. doi: 10.1016/j.cclet.2023.109285
18. [18]
  Caili Yang , Tao Long , Ruotong Li , Chunyang Wu , Yuan-Li Ding . Pseudocapacitance dominated Li₃VO₄ encapsulated in N-doped graphene via 2D nanospace confined synthesis for superior lithium ion capacitors. Chinese Chemical Letters, 2025, 36(2): 109675-. doi: 10.1016/j.cclet.2024.109675
19. [19]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
20. [20]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(670)
HTML views(4)

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