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Prebiotic Phosphorylation and Concomitant Oligomerization of Deoxynucleosides to form DNA
Author(s) -
Jiménez Eddy I.,
Gibard Clémentine,
Krishnamurthy Ramanarayanan
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202015910
Subject(s) - phosphodiester bond , dna , rna , nucleotide , chemistry , purine , biochemistry , pyrimidine , dna replication , biology , enzyme , gene
Recent demonstrations of RNA–DNA chimeras (RDNA) enabling RNA and DNA replication, coupled with prebiotic co‐synthesis of deoxyribo‐ and ribo‐nucleotides, have resurrected the hypothesis of co‐emergence of RNA and DNA. As further support, we show that diamidophosphate (DAP) with 2‐aminoimidazole (amido)phosphorylates and oligomerizes deoxynucleosides to form DNA—under conditions similar to those of ribonucleosides. The pyrimidine deoxynucleoside 5′‐O‐amidophosphates are formed in good (≈60 %) yields. Intriguingly, the presence of pyrimidine deoxynucleos(t)ides increased the yields of purine deoxynucleotides (≈20 %). Concomitantly, oligomerization (≈18–31 %) is observed with predominantly 3′,5′‐phosphodiester DNA linkages, and some (<5 %) pyrophosphates. Combined with previous observations of DAP‐mediated chemistries and the constructive role of RDNA chimeras, the results reported here help set the stage for systematic investigation of a systems chemistry approach of RNA–DNA coevolution.