Citation: Kun Chen, Zhiyong He, Wei Xiong, Chun-Jiang Wang, Xiang Zhou. Enantioselective Diels–Alder reactions with left-handed G-quadruplex DNA-based catalysts[J]. Chinese Chemical Letters, ;2021, 32(5): 1701-1704. doi: 10.1016/j.cclet.2020.12.047 shu

Enantioselective Diels–Alder reactions with left-handed G-quadruplex DNA-based catalysts

College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, Wuhan University, Wuhan 430072, China

xzhou@whu.edu.cn

Received Date: 4 November 2020
Revised Date: 21 December 2020
Accepted Date: 23 December 2020
Available Online: 29 December 2020

Figures(2)

Since the discovery of left-handed G-quadruplex (L-G4) structure formed by natural DNA, there has been a growing interest in its potential functions. This study utilised it to catalyse enantioselective Diels-Alder reactions, considering its different optical rotation compared to an ordinary G4. It was determined that when L-G4 was used with a combination of copper(Ⅱ) ions, there was a good enantioselectivity (-52% ee) without further addition of ligands. When further consideration was given by adding G4 ligands, G4 was further stabilised, even obtaining a better enantioselectivity (up to -80% ee). Moreover, when using ligands that have regulatory effects on G4, the ee value can be adjusted. In this work, a minimal left-handed G4 was reported. A follow-up study was also conducted, which recovers that the minimal left-handed G4 remains its catalytic effect and enantioselectivity, but is not so effective as the former case. This indicates that a complete G4 structure is relatively conducive to chiral catalysis.
- Diels–Alder reaction,
- Left-handed G-quadruplex,
- Asymmetric catalysis,
- Enantioselectivity,
- G-quadruplex ligand
1. [1]
  M. Frank-Kamenetskii, Nature 328(1987) 17-18. doi: 10.1038/328017a0
2. [2]
  A.J. Boersma, B.L. Feringa, G. Roelfes, Org. Lett. 9(2007) 3647-3650. doi: 10.1021/ol7015274
3. [3]
  (a) A.J. Boersma, J.E. Klijn, B.L. Feringa, G. Roelfes, J. Am. Chem. Soc. 130 (2008) 11783-11790.
  (b) Y.F. Wang, X. Zhang, C.C. Liu, X. Zhou, Acta Chim. Sin. 75 (2017) 692-698.
4. [4]
  A.J. Boersma, D. Coquiere, D. Geerdink, et al., Nat. Chem. 2(2010) 991-995. doi: 10.1038/nchem.819
5. [5]
  S. Park, H. Sugiyama, Angew. Chem. Int. Ed. 49(2010) 3870-3878. doi: 10.1002/anie.200905382
6. [6]
  S. Park, H. Sugiyama, Molecules 17(2012) 12792-12803. doi: 10.3390/molecules171112792
7. [7]
  A.J. Boersma, R.P. Megens, B.L. Feringa, G. Roelfes, Chem. Soc. Rev. 39(2010) 2083-2092. doi: 10.1039/b811349c
8. [8]
  G. Roelfes, B.L. Feringa, Angew. Chem. Int. Ed. 44(2005) 3230-3232. doi: 10.1002/anie.200500298
9. [9]
  N.S. Oltra, G. Roelfes, Acc. Chem. Res. (2008) 6039-6041.
10. [10]
  E.W. Dijk, B.L. Feringa, G. Roelfes, Tetrahedron: Asymmetry 19(2008) 2374-2377. doi: 10.1016/j.tetasy.2008.10.004
11. [11]
  J.T. Davis, G.P. Spada, Chem. Soc. Rev. 36(2007) 296-313. doi: 10.1039/B600282J
12. [12]
  A.I. Karsisiotis, N.M. Hessari, E. Novellino, et al., Angew. Chem. Int. Ed. 50(2011) 10645-10648. doi: 10.1002/anie.201105193
13. [13]
  L.X. Wang, J.F. Xiang, Y.L. Tang, Adv. Synth. Catal. 357(2015) 13-20. doi: 10.1002/adsc.201400818
14. [14]
  S. Neidle, S. Balasubramanian, Quadruplex Nucleic Acids, The Royal Society of Chemistry, London, 2006, pp. 1-30.
15. [15]
  C. Wang, G. Jia, J. Zhou, et al., Angew. Chem. Int. Ed. 51(2012) 9352-9355. doi: 10.1002/anie.201204850
16. [16]
  C. Wang, Y. Li, G. Jia, et al., Chem. Commun. 48(2012) 6232-6234. doi: 10.1039/c2cc31320k
17. [17]
  Y. Li, M. Cheng, J. Hao, et al., Chem. Sci. 6(2015) 5578-5585. doi: 10.1039/C5SC01381J
18. [18]
  W.J. Chung, B. Heddi, E. Schmitt, et al., Proc. Natl. Acad. Sci. U. S. A. 112(2015) 2729-2733. doi: 10.1073/pnas.1418718112
19. [19]
  B. Bakalar, B. Heddi, E. Schmitt, Y. Mechulam, A.T. Phan, Angew. Chem. Int. Ed. 58(2019) 2331-2335. doi: 10.1002/anie.201812628
20. [20]
  V.E. Gouverneur, K. Houk, B. de Pascual-Teresa, et al., Science 262(1993) 204-208. doi: 10.1126/science.8211138
21. [21]
  T.M. Tarasow, S.L. Tarasow, B.E. Eaton, Nature 389(1997) 54. doi: 10.1038/37950
22. [22]
  T. Ose, K. Watanabe, T. Mie, Nature 422(2003) 185. doi: 10.1038/nature01454
23. [23]
  A. Serganov, S. Keiper, L. Malinina, Nat. Struct. Mol. Biol. 12(2005) 218-224. doi: 10.1038/nsmb906
24. [24]
  M.T. Reetz, N. Jiao, Angew. Chem. Int. Ed. 45(2006) 2416-2419. doi: 10.1002/anie.200504561
25. [25]
  A.J. Boersma, J.E. Klijn, B.L. Feringa, G. Roelfes, J. Am. Chem. Soc. 130(2008) 11783-11790. doi: 10.1021/ja803170m
26. [26]
  X. Xu, W. Mao, F. Lin, Catal. Commun. 74(2016) 16-18. doi: 10.1016/j.catcom.2015.09.012
27. [27]
  S. Otto, F. Bertoncin, J.B. Engberts, J. Am. Chem. Soc. 118(1996) 7702-7707. doi: 10.1021/ja960318k
28. [28]
  P. Murat, Y. Singh, E. Defrancq, Chem. Soc. Rev. 40(2011) 5293-5307. doi: 10.1039/c1cs15117g
29. [29]
  B.S. Fu, J.G. Huang, Y.Q. Chen, et al., Chem. Commun. 52(2016) 10052-10055. doi: 10.1039/C6CC04866H
30. [30]
  S. Muller, S. Kumari, R. Rodriguez, S. Balasubramanian, Nat. Chem. 2(2010) 1095-1098. doi: 10.1038/nchem.842
31. [31]
  K.A. Ahrendt, C.J. Borths, D.W.C. Macmillan, J. Am. Chem. Soc. 122(2000) 4243-4244. doi: 10.1021/ja000092s
1. [1]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
2. [2]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
3. [3]
  Yiming Yang , Lichao Sun , Qingfeng Zhang . Plasmonic nanocrystals with intrinsic chirality: Biomolecule-directed synthesis and applications. Chinese Journal of Structural Chemistry, 2025, 44(1): 100467-100467. doi: 10.1016/j.cjsc.2024.100467
4. [4]
  Cong Gao , Zijian Zhu , Siwei Li , Zheng Xi , Qingqing Sun , Jie Han , Rong Guo . Chiral supramolecular catalysts of helical nanoribbon: More twist, higher enantioselectivity. Chinese Chemical Letters, 2025, 36(3): 109968-. doi: 10.1016/j.cclet.2024.109968
5. [5]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
6. [6]
  Pan-Pan Hua , Hui-Jun Feng , Shu-Ning Lan , Francisco Aznarez , Li-Fang Zhang . Post-modification-induced supramolecular transformation of Hopf link to macrocycle. Chinese Chemical Letters, 2025, 36(6): 110684-. doi: 10.1016/j.cclet.2024.110684
7. [7]
  Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
8. [8]
  Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
9. [9]
  Ji-Jia Zhou , Li-Gao Liu , Zhen-Tao Zhang , Hao-Xuan Dong , Xin Lu , Zhou Xu , Xin-Qi Zhu , Bo Zhou , Long-Wu Ye . Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement. Chinese Chemical Letters, 2025, 36(9): 110870-. doi: 10.1016/j.cclet.2025.110870
10. [10]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
11. [11]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
12. [12]
  Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
13. [13]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
14. [14]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
15. [15]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
16. [16]
  Kai Zhu , Lei Yang , Yang Yang , Yanqi Wu , Fengzhi Zhang . Recent advances toward the catalytic enantioselective synthesis of planar chiral cyclophanes. Chinese Chemical Letters, 2025, 36(7): 110678-. doi: 10.1016/j.cclet.2024.110678
17. [17]
  Jun Liu , Zhaoyu Feng , Renming Pan , Xiaolong Yu , Meijuan Zhou , Gang Zhao , Hongyu Wang . Enantioselective regulation to coronal polyheterocyclic compounds via phosphonium salt-catalyzed cycloadditions of azomethine imines with γ-butenolides. Chinese Chemical Letters, 2025, 36(8): 110647-. doi: 10.1016/j.cclet.2024.110647
18. [18]
  Guodong Wang , Mengying Jia , Haitao Liu , Yong Liu , Zhiguo Zhang , Xianxiu Xu . Expeditious synthesis and applications of isoquinoline ring-modified Quinap derivatives. Chinese Chemical Letters, 2025, 36(8): 110705-. doi: 10.1016/j.cclet.2024.110705
19. [19]
  Bingbing Dong , Junmin Zhang , Xiang-Yu Ye , Xuan Huang , Yonggui Robin Chi . Catalytic construction of P-stereogenic center via phosphorus-centered nucleophilic substitution. Chinese Chemical Letters, 2025, 36(9): 111052-. doi: 10.1016/j.cclet.2025.111052
20. [20]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1547)
HTML views(149)

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