Citation: Jianxi Ying, Ruiwen Ding, Yumeng Zhang, Bowen Han, Yeting Guo, Ning Wang, Dandan Guo, Yile Wu, Junwei Huang, Yan Liu, Feng Ni, Shaohua Huang, Yufen Zhao. Trimetaphosphate-induced chiral selection between amino acid and nucleoside using ¹⁵N-³¹P coupling NMR[J]. Chinese Chemical Letters, ;2022, 33(2): 821-824. doi: 10.1016/j.cclet.2021.07.031 shu

Trimetaphosphate-induced chiral selection between amino acid and nucleoside using ¹⁵N-³¹P coupling NMR

Jianxi Ying ^{a, b} ,
Ruiwen Ding ^{a, b} ,
Yumeng Zhang ^c ,
Bowen Han ^{a, b} ,
Yeting Guo ^{a, b} ,
Ning Wang ^{a, b} ,
Dandan Guo ^{a, b} ,
Yile Wu ^{a, b} ,
Junwei Huang ^c ,
Yan Liu ^c ,
Feng Ni ^{a, b} ,
Shaohua Huang ^{a, b, *} ,
Yufen Zhao ^{a, b, c, d, *}

a.
Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, China
b.
Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo 315211, China
c.
Department of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
d.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China

huangshaohua@nbu.edu.cn

zhaoyufen@nbu.edu.cn

Received Date: 10 May 2021
Revised Date: 8 July 2021
Accepted Date: 9 July 2021
Available Online: 16 July 2021

Figures(4)

Life on Earth uses a common set of l-amino acids (l-aa) to construct proteins and d-nucleosides (d-Nu) to form nucleic acids, which serve as the carrier of genetic information. Herein, we reveal the intrinsic mechanism of chiral selection of l-aa and d-Nu from the perspective of chemical origin of life. This work employed ¹⁵N-labeled l-aa and performed one-pot synthesis of nucleotide amidate of amino acid (N-aa-NMP) using equal amounts of l-¹⁵N-aa and d-¹⁴N-aa with d-/l-Nu in the aqueous solution of trimetaphosphate, generating l-¹⁵N-aa-NMP and d-¹⁴N-aa-NMP, respectively. The ³¹P-NMR data indicated that l-aa was preferentially selected during the formation of N-aa-NMP in the presence of d-Nu. Surprisingly, d-aa was preferred over l-aa in the presence of l-Nu. Further analysis revealed that l-¹⁵N-aa-d-NMP vs. d-¹⁴N-aa-l-NMP and d-¹⁴N-aa-d-NMP vs. l-¹⁵N-aa-l-NMP were mirror isomers of each other, respectively. These data suggest that there could be a set of chiral systems opposite to that on Earth, which infers there might be a world of life that is a mirror image of the Earth.
- Chiral selection,
- Amino acids,
- Nucleosides,
- Prebiotic chemistry,
- Origin of life
1. [1]
  G.L. Rikken, E. Raupach, Nature 405(2000) 932-935. doi: 10.1038/35016043
2. [2]
  M.A. Famiano, R.N. Boyd, T. Kajino, T. Onaka, Astrobiology 18(2018) 190-206. doi: 10.1089/ast.2017.1686
3. [3]
  A. Oda, T. Nakayoshi, S. Fukuyoshi, et al., Chirality 30(2018) 332-341. doi: 10.1002/chir.22821
4. [4]
  M.F. Guasti, Phys. Lett. A 383(2019) 3180-3186. doi: 10.1016/j.physleta.2019.06.002
5. [5]
  A. Yachmenev, J. Onvlee, E. Zak, A. Owens, J. Kupper, Phys. Rev. Lett. 123(2019) 243202. doi: 10.1103/PhysRevLett.123.243202
6. [6]
  C. Viedma, Phys. Rev. Lett. 94(2005) 065504. doi: 10.1103/PhysRevLett.94.065504
7. [7]
  R.M. Hazen, T.R. Filley, G.A. Goodfriend, Proc. Natl. Acad. Sci. 98(2001) 5487-5490. doi: 10.1073/pnas.101085998
8. [8]
  X.C. Ye, J.X. Cui, B.W. Li, et al., Nat. Commun. 10(2019) 1964. doi: 10.1038/s41467-019-09997-y
9. [9]
  J. Bailey, A. Chrysostomou, J.H. Hough, et al., Science 281(1998) 672-674. doi: 10.1126/science.281.5377.672
10. [10]
  J.Y. Wang, G.L. Zhuang, M.Q. Chen, et al., Angew. Chem. Int. Ed. 59(2020) 1619-1626. doi: 10.1002/anie.201909401
11. [11]
  J.Y. Kim, J. Yeom, G.P. Zhao, et al., J. Am. Chem. Soc. 141(2019) 11739-11744. doi: 10.1021/jacs.9b00700
12. [12]
  J. Yeom, B. Yeom, H. Chan, et al., Nat. Mater. 14(2015) 66-72. doi: 10.1038/nmat4125
13. [13]
  P. Yin, Z.M. Zhang, H. Lv, et al., Nat. Commun. 6(2015) 6475. doi: 10.1038/ncomms7475
14. [14]
  C. Viedma, J.M. McBride, B. Kahr, P. Cintas, Angew. Chem. Int. Ed. 52(2013) 10545-10548. doi: 10.1002/anie.201303915
15. [15]
  P.G. Higgs, N. Lehman, Nat. Rev. Genet. 16(2015) 7-17. doi: 10.1038/nrg3841
16. [16]
  W. Gilbert, Nature 319(1986) 618-618.
17. [17]
  P. Schimmel, Annu. Rev. Biochem. 56(1987) 125-158. doi: 10.1146/annurev.bi.56.070187.001013
18. [18]
  M. Ibba, D. Soll, Annu. Rev. Biochem. 69(2000) 617-650. doi: 10.1146/annurev.biochem.69.1.617
19. [19]
  D. Soll, Nucleic Acids Symp. Ser. (Oxf) (2004) 283-284.
20. [20]
  K. Tamura, P. Schimmel, Science 305(2004) 1253-1253. doi: 10.1126/science.1099141
21. [21]
  K. Tamura, P.R. Schimmel, Proc. Natl. Acad. Sci. U. S. A. 103(2006) 13750-13752. doi: 10.1073/pnas.0606070103
22. [22]
  K. Tamura, Int. J. Mol. Sci. 12(2011) 4745-4757. doi: 10.3390/ijms12074745
23. [23]
  H. Griesser, M. Bechthold, P. Tremmel, E. Kervio, C. Richert, Angew. Chem. Int. Ed. 129(2017) 1244-1248. doi: 10.1002/ange.201610651
24. [24]
  N.S. Wickramasinghe, J.C. Lacey, Orig. Life Evol. Biospheres 22(1992) 361-368. doi: 10.1007/BF01809372
25. [25]
  J.P. Biron, A.L. Parkes, R. Pascal, J.D. Sutherland, Angew. Chem. Int. Ed. 44(2005) 6731-6734. doi: 10.1002/anie.200501591
26. [26]
  J. Ying, S. Fu, X. Li, et al., Chem. Commun. 54(2018) 8598-8601. doi: 10.1039/C8CC04767G
27. [27]
  T. Wang, P. Zhang, G. Hu, et al., ChemistrySelect 3(2018) 7849-7855. doi: 10.1002/slct.201800965
28. [28]
  D.S. Kelley, J.A. Karson, D.K. Blackman, et al., Nature 412(2001) 145-149. doi: 10.1038/35084000
29. [29]
  W. Martin, J. Baross, D. Kelley, M.J. Russell, Nat. Rev. Microbiol. 6(2008) 805-814. doi: 10.1038/nrmicro1991
30. [30]
  J. Lacey Jr, D. Mullins, Orig. Life 13(1983) 3-42. doi: 10.1007/BF00928761
31. [31]
  Z. Wang, W. Xu, L. Liu, T.F. Zhu, Nat. Chem. 8(2016) 698-704. doi: 10.1038/nchem.2517
32. [32]
  J.J. Ling, C. Fan, H. Qin, et al., Angew. Chem. Int. Ed. 59(2020) 3724-3731. doi: 10.1002/anie.201914799
1. [1]
  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
2. [2]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
3. [3]
  Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
4. [4]
  Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
5. [5]
  Min-Hang Zhou , Jun Jiang , Wei-Min He . EDA-complexes-enabled photochemical synthesis of α-amino acids with imines and tetrabutylammonium oxalate. Chinese Chemical Letters, 2025, 36(1): 110446-. doi: 10.1016/j.cclet.2024.110446
6. [6]
  Huan Yao , Jian Qin , Yan-Fang Wang , Song-Meng Wang , Liu-Huan Yi , Shi-Yao Li , Fangfang Du , Liu-Pan Yang , Li-Li Wang . Ultra-highly selective recognition of nucleosides over nucleotides by rational modification of tetralactam macrocycle and its application in enzyme assay. Chinese Chemical Letters, 2024, 35(6): 109154-. doi: 10.1016/j.cclet.2023.109154
7. [7]
  Cheng Guo , Xiaoxiao Zhang , Xiujuan Hong , Yiqiu Hu , Lingna Mao , Kezhi Jiang . Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(4): 108867-. doi: 10.1016/j.cclet.2023.108867
8. [8]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
9. [9]
  Weiwei He , Hongbo Zhang , Xudong Lin , Lili Zhu , Tingting Zheng , Hao Pei , Yang Tian , Min Zhang , Guoyue Shi , Lei Wu , Jianlong Zhao , Gulinuer Wumaier , Shengqing Li , Yufang Xu , Honglin Li , Xuhong Qian . Advancements in life-on-a-chip: The impact of "Beyond Limits Manufacturing" technology. Chinese Chemical Letters, 2024, 35(5): 109091-. doi: 10.1016/j.cclet.2023.109091
10. [10]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
11. [11]
  Peiwen Liu , Fang Zhao , Jing Zhang , Yunpeng Bai , Jinxing Ye , Bo Bao , Xinggui Zhou , Li Zhang , Changlu Zhou , Xinhai Yu , Peng Zuo , Jianye Xia , Lian Cen , Yangyang Yang , Guoyue Shi , Lin Xu , Weiping Zhu , Yufang Xu , Xuhong Qian . Micro/nano flow chemistry by Beyond Limits Manufacturing. Chinese Chemical Letters, 2024, 35(5): 109020-. doi: 10.1016/j.cclet.2023.109020
12. [12]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
13. [13]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
14. [14]
  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
15. [15]
  Yao-Hua Gu , Yu Chen , Qing Li , Neng-Bin Xie , Xue Xing , Jun Xiong , Min Hu , Tian-Zhou Li , Ke-Yu Yuan , Yu Liu , Tang Tang , Fan He , Bi-Feng Yuan . Metabolome profiling by widely-targeted metabolomics and biomarker panel selection using machine-learning for patients in different stages of chronic kidney disease. Chinese Chemical Letters, 2024, 35(11): 109627-. doi: 10.1016/j.cclet.2024.109627
16. [16]
  Zhenqiang Guo , Huicong Yang , Qian Wei , Shengjun Xu , Guangjian Hu , Shuo Bai , Feng Li . Dual-additives enable stable electrode-electrolyte interfaces for long life Li-SPAN batteries. Chinese Chemical Letters, 2024, 35(5): 108622-. doi: 10.1016/j.cclet.2023.108622
17. [17]
  Lingna Wang , Chenxin Tian , Ruobin Dai , Zhiwei Wang . Eco-friendly regeneration of end-of-life PVDF membrane with triethyl phosphate: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(9): 109356-. doi: 10.1016/j.cclet.2023.109356
18. [18]
  Ning DING , Siyu WANG , Shihua YU , Pengcheng XU , Dandan HAN , Dexin SHI , Chao ZHANG . Crystalline and amorphous metal sulfide composite electrode materials with long cycle life: Preparation and performance of hybrid capacitors. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1784-1794. doi: 10.11862/CJIC.20240146
19. [19]
  Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4^th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
20. [20]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(753)
HTML views(46)

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

Trimetaphosphate-induced chiral selection between amino acid and nucleoside using 15N-31P coupling NMR

Metrics

通讯作者: 陈斌, bchen63@163.com

Trimetaphosphate-induced chiral selection between amino acid and nucleoside using ¹⁵N-³¹P coupling NMR