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
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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

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通讯作者: 陈斌, bchen63@163.com

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