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

作　　者：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 

机构地区：[1]Institute of Drug Discovery Technology,Ningbo University,Ningbo 315211,China [2]Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences,Ningbo University,Ningbo 315211,China [3]Department of Chemical Biology,College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China [4]Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology(Ministry of Education),Department of Chemistry,Tsinghua University,Beijing 100084,China

出　　处：《Chinese Chemical Letters》2022年第2期821-824,共4页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China (Nos.91856126,42003062,21778042 and 41876072);Scientific Research Grant of Ningbo University (No.215432000282);Ningbo Top Talent Project (No.215-432094250)。

摘　　要：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 in-trinsic 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.Surpris-ingly,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,respec-tively.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.

关 键 词：Chiral selection Amino acids NUCLEOSIDES Prebiotic chemistry Origin of life 

分 类 号：Q-05[生物学]