Trimetaphosphate-induced chiral selection between amino acid and nucleoside using ~(15)N-~(31)P coupling NMR
Trimetaphosphate-induced chiral selection between amino acid and nucleoside using ~(15)N-~(31)P coupling NMR
复制标题
使用 ~(15)N-~(31)P 耦合 NMR 进行三偏磷酸诱导的氨基酸和核苷之间的手性选择
DOI：
10.1016/j.cclet.2021.07.031
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发表时间：
2022
影响因子：
9.1
通讯作者：
Zhao Yufen
中科院分区：
文献类型：
--
作者：
Ying Jianxi;Ding Ruiwen;Zhang Yumeng;Han Bowen;Guo Yeting;Wang Ning;Guo D;an;Wu Yile;Huang Junwei;Liu Yan;Ni Feng;Huang Shaohua;Zhao Yufen
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 ~(15)N-labeled L-aa and performed one-pot synthesis of nucleotide amidate of amino acid (N-aa-NMP) using equal amounts of L-~(15)N-aa and D-~(14)N-aa with D-/L-Nu in the aqueous solution of trimetaphosphate,generating L-~(15)N-aa-NMP and D-~(14)N-aa-NMP,respectively.The ~(31)P-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-~(15)N-aa-D-NMP vs.D-~(14)N-aa-l-NMP and D-~(14)N-aa-D-NMP vs.l-~(15)N-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.
